Aug. 27, 2026

The Tinder Trap: The Murder of Sydney Loofe – Aubrey Trail & Bailey Boswell

The Tinder Trap: The Murder of Sydney Loofe – Aubrey Trail & Bailey Boswell
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Season 10

On November 15, 2017, 24-year-old Sydney Loofe left her Lincoln apartment excited for a second Tinder date. She posted a Snapchat: “Ready for my date.” She never came home.The woman she matched with was Bailey Boswell.
Sydney didn’t know Boswell lived with older boyfriend Aubrey Trail — a career criminal prosecutors said was already looking for someone to kill. Boswell lured Sydney to a basement apartment in Wilber. There she was strangled with an extension cord, cut into 14 pieces, stuffed into trash bags, and dumped along rural roads. For three weeks her family and the FBI searched. Then the bags were found.
Store video showed Trail and Boswell buying saws and bleach while Sydney was still alive.
Trail was sentenced to death. Boswell got life. In 2024 her conviction was upheld. Sydney just wanted a second date. What she walked into was a trap set before they ever matched.

Timestamps:
03:51 Sidney Loof
14:26 Aubrey Trail’s Criminal Past
18:27 Bailey Boswell’s Fall
25:21 The Wilbur Basement
29:00 Tinder Trap Set
38:07 Trials and Verdicts
41:37 Justice After Loss

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WEBVTT

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Hey everyone, welcome back to Bloody Angola. I'm your host

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Jim Chapman, continuing the series 50 Shades of Evil. I'm

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taking you back to Nebraska for a second time for

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this one, and we're going to go to the evening

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of November 15th, 2017, when a 24-year-old woman named Sydney

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Loof stood in her Lincoln, Nebraska apartment and did something

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millions of people do every single day. She opened up

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a dating app. She checked her messages and she got

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ready for a second date. Now, she even posted a

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Snapchat story. And the caption, it was simple.

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It was ordinary.

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She just put, ready for my date with a picture

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of herself. Sidney had already met this woman once. The

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first evening had gone well. She had told a friend

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she thought she may have found her dream girl. The

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woman on the other end of the messages called herself Audrey.

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She was friendly, she was attentive, and she had reassured

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Sidney twice that it would just be the two of them. Now,

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Sidney left her apartment that night, drove roughly 40 minutes

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south to the small town of Wilbur, And the way

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we know this is her phone pinged near a basement

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apartment on a quiet residential street, and then it went dark.

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She never came home. Three weeks later, searchers walking gravel

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roads in Nebraska in a rural county called Clay County,

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they began finding plastic trash bags scattered into ditches. And

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in those bags were the carefully cut remains of a

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young woman. 14 pieces in total. One arm still carried

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a tattoo that read, Everything will be wonderful someday. Some

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of her organs were never recovered. Near the bags lay

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a plastic sauna suit with the crotch cut out, sex toys,

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a dog leash, latex gloves, and pieces of extension cord.

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And the woman Sidney believed was Audrey was not Audrey

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at all. She was a 23-year-old by the name of

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Bailey Marie Boswell. And waiting inside that Wilbur basement was

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Boswell's 50-year-old boyfriend, a longtime fraudster and a con man

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named Aubrey Clifton Trail. Prosecutors would later prove that hours

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before Sidney ever left work at the Menard store where

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she was a cashier, Trail and Boswell had already been shopping.

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Surveillance cameras and receipts would capture them buying hacksaws. 10 snips,

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a utility knife, and extra blades. Large quantities of bleach

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in the exact brand of trash bags that would later

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hold her body. Now, while Sidney was still alive and

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still on the clock, the tools of her dismemberment were

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already in their possession. So this is a story of

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how an ordinary tender connection became a calculated murder. It's

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the story of two people who turned a young woman's

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desire for companionship into a night of strangulation, sexual violence,

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and methodical disposal of her body. And it's the story

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of how the Nebraska justice system ultimately decided their fate.

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Death for one, life without possibility of parole for the other.

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So let's get into it. And before we talk about

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the people who took her life, we need to spend

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some time with the young woman they took from this world.

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Because if we start with the killers, we're turning Sidney

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Loof into a plot point. rather than into a person.

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And she was very much a person and deeply loved.

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She was born on August 21st, 1993 in Broken Bow, Nebraska.

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Her parents were George and Susie Loof. George, he was

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an educator through and through. a teacher, a coach, and

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even later, a principal. And Susie, she also worked in education,

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eventually becoming a special ed teacher. They were the kind

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of couple who built their lives around schools and their

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small town community. Now, the family did live for a

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time in what's known as Arcadia, which is a tiny

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central Nebraska town And that's where Sidney would spend her

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earliest years along her older brother, Levi, and later a

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younger sister named Mackenzie. And these three siblings, they were close.

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Family members later remembered a childhood full of the simple

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things that would define rural Nebraska, like swinging on a

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tree swing, riding bikes to a local pool in the summertime,

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even sledding in the wintertime. and spending long hours outdoors. Now, Sydney,

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was also known as a tomboy. Her mother Susie would

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later say she could outfish most of her family. She

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always wanted to tag along with her father and her

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brother when they went fishing. And the loose fish near Yankton,

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South Dakota, along the Missouri River, just beautiful areas to

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see all this wonderful fishing. And those trips became a

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part of the fabric of this family life that they spent. Sydney,

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she loved the water, the quiet, the patience of it,

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and just being outdoors. George would coach her junior high

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basketball team, and he recalled her as just a natural

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in sports. He would say she had a great baseline jumper.

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And she also played golf and was really good at

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that as well. Teachers and family described her as a

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girl who was active and very competitive. but all that

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would change in her teenage years. Sydney would unfortunately develop scoliosis,

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which is a curvature of the spine, and that made

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physical activity very painful for her, especially swinging a golf club.

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basketball would become difficult. And that active lifestyle that had

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defined her childhood was largely taken away from her. It

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was a significant loss for this girl who had defined

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herself partly through movement and through the outdoors, but fishing

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would remain and she would make the best of just

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a horrible situation for her in her younger years. She

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was very determined to make the best of that. Now,

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around the year 2000, the family would move to Nellie, Nebraska,

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which is a town of roughly 1500 people. It's in

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the northeast area of Nebraska. And that became home for them.

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Just this small town of 1500 people. Sydney would attend

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the local schools all the way from second grade through

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graduation in May of 2011. And in a town that size,

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the school is really the center of life. If you're

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from a small town, you get that. It's all about

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high school, Friday night lights, and baseball games in the spring.

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And that's exactly what it was like there. Now, after

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graduating in 2011, Sidney began working as a cashier at

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what was known as Menard's Store. And she stayed there

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for about two years. She then transfers to another location

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of that store that was in Lincoln, Nebraska. And there

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was a reason for that. Her brother and sister lived

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in the Lincoln area at the time. and she wanted

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to be closer to her siblings.

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Made a lot of sense.

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It spoke to her family spirit, if you will, and

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these siblings would stay connected even as adults. Kenzie would

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come over to watch Netflix, make dinner, and help tidy

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up because, according to her, Sydney hated cleaning up. Levi

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would be counted on to be there when her car

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would break down or when she would have problems. And

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that happened more than once. One time it died 200

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yards from where he lived, and he tracked her down

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and helped her fill the tank to get it running again.

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She was out of gas.

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Cindy also raised a cat named Mimsy from a kitten

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that she had bought off Craigslist and she adored that cat.

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Mimsy was still in her apartment without food and water

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when the family would force entry after she went missing

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and that detail would stay with them. She was known

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as one of the kindest, most polite cashier's customers. And

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co-workers would later tell the family how much they loved

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just seeing her and her big smile. And she worked

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very hard. And her brother would remember later when she

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received her first bonus how much pride she beamed with.

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She felt like her hard work was being rewarded and

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it was validation, right? But Menards was never the end

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goal for Sidney. She actually dreamed of working with animals

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at a veterinary clinic. And she had a soft spot

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for creatures that needed care and that same softness that

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she would extend to people. As a matter of fact,

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on at least three occasions that her parents would later recall,

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Sidney took in people that were struggling. She gave them

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a place to stay while they worked through problems. And

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one specific story involved a younger male co-worker who was

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living in what you would classify as substandard conditions. Sidney

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would let him stay at her apartment.

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She taught him how to save money.

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She helped him with basic hygiene and life skills until

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he could find a place of his own. And when

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asked why she would do that for someone that she

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barely knew, The answers she gave, according to those who

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knew her, were simple. Everybody needs help at some point

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in their life. Her brother Levi put it this way,

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Sidney was the poster person for caring more about others

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than she did for herself. In that quality, it made

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her family proud. It also made the later news of

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what happened to her almost impossible to understand or absorb.

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That same young woman who had opened her home to

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help people in need was the one who would be

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targeted by two animals, if you will, who saw her

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as a means to an end. By 2017, Sydney was

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24 years old. She was living in Lincoln. She maintained

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regular contact with her parents. I'm talking phone calls and

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texts two, three, four, five times a week. And the

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drive between where her parents lived and Lincoln was about

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three hours. So check-ins mattered. She wasn't just right down

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the street if you were worried. She was responsible.

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She shut up for.

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Work all the time without fail, no exception, was very

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on time as a person, and friends and family said

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she didn't simply vanish without explanation ever. Now, despite all that,

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she was struggling. Susie later recounted that her daughter suffered

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from anxiety and major depression, and in the days leading

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up to her disappearance, Sidney would talk to her family

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about her struggles with mental health. They scheduled a doctor's appointment,

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drove her to get antidepressants, and that visit was the

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last time her immediate family would see her in person.

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The weekend before she went missing, Sydney went back to

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visit her parents. She spent time with family and friends

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and she just had a great weekend. It was the

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kind of weekend that happens with close families all the time. Now,

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Sydney also used dating apps like everybody else her age, right?

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She was looking for connection. She wanted companionship. She wanted

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someone who saw her and just was.

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Blown away by that. She wanted to fall in love, right?

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In early November of 2017, she matched with a woman

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who called herself Audrey. And the messages were friendly. Sidney

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asked careful questions. She made plans, and after the first date,

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she even told her friend, you know, I may have

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found my dream girl here. On the evening of November 15th,

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she posted a Snapchat story that I told you about earlier,

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where she just put, ready for my date, with the picture,

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and left her apartment. Her cat, Mimsy, was there. Her

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car would still be in the driveway somewhere. The next day,

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her purse, her glasses, the ordinary objects that if you're

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going to disappear for a little while, you're going to

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take with you, they were all found inside of her house.

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But Sidney herself would not return. When she failed to

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show up for work the next day at Menards, this

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was on November 16th, her co-workers became worried. They knew her,

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and they knew this was not like her. Word reached

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her sister. Her sister then called her parents, and George

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and Susie would try to reach her. One of the

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texts that Susie sent to Sidney just read, please, Sidney,

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you're scaring me. Now, by the evening of the 16th,

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they had reported her missing to the Lincoln Police Department,

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and the search that would follow would consume the next

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three weeks of their lives, and it would leave a

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permanent mark on the Nebraska town that had watched Sidney

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grow up. Now, If Sidney Loof's story is one of

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relative stability, loving family, rooted in small-town Nebraska, Aubrey Trail's

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life sits at the opposite end of that spectrum. Aubrey

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was born in 1967, and look, details of his early

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life are cloudy, but what is clear is that by

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the age of 17, he was already in serious trouble

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with the law. He was imprisoned in Tennessee for armed

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robbery at that age of a motel, and that conviction

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marked the start of a long pattern of incarceration and release.

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that would stretch across multiple states for decades. Now, the

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armed robbery is significant, not only because it put him

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in prison so young, but because it established an early

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willingness to use force or threat of force in the

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commission of a crime. He didn't care if he had

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to pull a gun on somebody. And from that point forward,

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this guy's record shifted more heavily toward fraud, forgery, and theft.

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Crimes of deception rather than overt violence. But the capacity

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for control and intimidation never left this guy. And as

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an adult, Trell would develop a particular specialty, antiques and

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rare coin collecting fraud. He moved through communities and he

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would present himself as this knowledgeable coin.

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Dealer, right?

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Someone who understood the value of collectibles, right? and maybe

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some antiques if they had those, and he would facilitate

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these high-dollar transactions. But in reality, those schemes would involve

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00:16:17.100 --> 00:16:22.120
passing bad checks or inflating what the value of something

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he was selling was to the point that it was robbery.

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And he would fabricate deals with people. He's just a

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total scumbag, Connors. And Trell would target antique malls or

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individual coin collectors. He would present himself as a serious

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00:16:36.500 --> 00:16:40.309
buyer and just screw them out of everything they had.

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And he didn't just do this in Nebraska, Pennsylvania, Tennessee.

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He would go all over the place. An Iowa antique

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00:16:48.269 --> 00:16:52.590
store owner later described the frustration of dealing with him as.

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Impossible. Now, understand this. Trell was not.

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00:16:57.330 --> 00:17:03.269
A successful, legitimate businessman who occasionally maybe stepped outside of

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00:17:03.309 --> 00:17:06.799
the law. This guy was a career criminal. His primary

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00:17:06.890 --> 00:17:10.920
skill was persuading people and lying to them. And he

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00:17:10.940 --> 00:17:14.720
could talk. He could present a version of himself that

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00:17:14.839 --> 00:17:18.500
sounded credible to people that wanted to believe they were

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00:17:18.539 --> 00:17:23.220
dealing with someone somewhat sophisticated. Now, that same skill set,

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00:17:23.319 --> 00:17:28.059
the ability to present this compelling story to offer financial

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00:17:28.160 --> 00:17:33.410
help or access or position himself as a provider or

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authority figure, that would later be turned toward young women.

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In the years leading up to 2017, Trail and a

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00:17:42.789 --> 00:17:47.579
woman named Bailey Boswell would use dating apps and other

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platforms to draw women.

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Women in their circles.

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And they would talk about some strange shit to lure victims.

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They would talk about witches, a coven, vampires. They would

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00:17:58.460 --> 00:18:02.609
offer financial support in exchange for obedience to a set

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00:18:02.640 --> 00:18:08.150
of rules. And women were recruited 50 shades of gray style, right?

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00:18:08.650 --> 00:18:14.470
Rules were imposed, check-ins every few hours, restrictions on other relationships,

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00:18:14.970 --> 00:18:19.349
expectations of sex, and money and housing restricted. were offered

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00:18:19.630 --> 00:18:23.569
as incentives. And they would prey on these women that

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had nothing but vulnerability in front of them. So I

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brought up Bailey Boswell. Let's talk about her a little bit.

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Her story begins in a very different place from the

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one where it eventually ends. And if Aubrey Trails Early

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00:18:41.500 --> 00:18:46.059
years were defined by instability and all his bullshit through

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00:18:46.099 --> 00:18:51.130
the criminal justice system Bailey's childhood carried. I guess the

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markers of a more conventional life. small-town American life, at

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00:18:55.200 --> 00:18:59.220
least on the surface. She was raised in Leon, Iowa,

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00:18:59.359 --> 00:19:01.859
a quiet community. It was in the southern part of

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00:19:01.900 --> 00:19:05.559
the state, and her biological father was actually murdered when

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00:19:05.619 --> 00:19:08.619
she was still an infant. Now, the circumstances, according to

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00:19:08.720 --> 00:19:14.019
family accounts shared during her sentencing, involved a drug-related dispute,

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00:19:14.259 --> 00:19:17.980
and after his death, Bailey was raised by her mother,

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00:19:18.140 --> 00:19:23.529
Priscilla and her stepfather, Jeff Boswell, who adopted her. By

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00:19:23.630 --> 00:19:27.279
most descriptions offered by her family, the household that followed

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00:19:27.359 --> 00:19:31.359
was stable and supportive. She had siblings, and she seemingly

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00:19:31.599 --> 00:19:34.650
lived a normal life, and she was a standout high

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00:19:34.690 --> 00:19:38.289
school athlete. She excelled in basketball and track.

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She was fast.

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00:19:39.599 --> 00:19:42.700
She could score points on the basketball court. And she

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was the kind of player who drew attention from coaches

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00:19:46.390 --> 00:19:50.779
and classmates, family members, and people who knew her intimately. Leon,

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00:19:51.039 --> 00:19:55.299
Iowa later described her as bubbly, outgoing, popular, the girl

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00:19:55.339 --> 00:19:58.539
who would buy breakfast for her young siblings on the

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00:19:58.579 --> 00:20:01.109
way to school. and seemed to have like a clear,

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00:20:01.289 --> 00:20:04.650
great path ahead of her in life. She even received

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00:20:04.890 --> 00:20:09.049
interest from colleges and was offered a partial scholarship to

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00:20:09.089 --> 00:20:12.660
play basketball. And for a young woman from a small town,

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00:20:12.980 --> 00:20:17.119
that kind of opportunity represents more than just sports. It

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00:20:17.200 --> 00:20:21.630
represents a ticket out to A chance to a different

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00:20:21.750 --> 00:20:26.289
scale of life. A future that feels open. And teachers

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00:20:26.430 --> 00:20:29.339
and community members, they saw a lot of promise in her.

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00:20:29.799 --> 00:20:33.519
I'm telling you, from the outside, looking upward, it looked

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00:20:33.539 --> 00:20:38.599
like this girl was going to have just a star-bound life. Now,

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00:20:38.720 --> 00:20:43.029
after high school... That's when things started to unravel for her.

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00:20:43.509 --> 00:20:47.170
Bailey went off toward college with athletics on her mind

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00:20:47.250 --> 00:20:51.750
and a lot of opportunity. Then the supports that had

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00:20:51.869 --> 00:20:55.990
held her began to fray. There are accounts of sexual

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00:20:56.049 --> 00:20:59.769
assault at a party. There are accounts of substance abuse.

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00:21:00.269 --> 00:21:04.490
And there's a destructive relationship that family members have. would

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00:21:04.549 --> 00:21:08.230
later define as the turning point for her. She became

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00:21:08.289 --> 00:21:11.039
involved with a man named Freddie, and according to her

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00:21:11.119 --> 00:21:17.059
parents and other relatives, he was physically, emotionally, and sexually abusive.

307
00:21:17.480 --> 00:21:22.470
More than that, they say he coerced her into commercial sex,

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00:21:22.549 --> 00:21:27.190
basically pimped her out. And Bailey was young, and the

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00:21:27.230 --> 00:21:32.809
relationship obviously would accelerate downward. She had a daughter during

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00:21:32.849 --> 00:21:36.890
this period, and as the abuse and the instability continued,

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00:21:37.319 --> 00:21:41.579
custody of the little girl was ultimately placed with relatives.

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00:21:41.920 --> 00:21:46.559
Bailey's parents would describe watching their daughter change. This bubbly,

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00:21:46.759 --> 00:21:51.039
athletic teenager they had known was harder to locate in

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00:21:51.059 --> 00:21:54.900
the young woman who became entangled with this abusive partner

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00:21:55.319 --> 00:22:00.160
and struggling mother. to maintain stability. Now, in 2016, while

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00:22:00.220 --> 00:22:04.400
living in the Cameron, Missouri area, Bailey was fined for

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00:22:04.480 --> 00:22:06.660
possession of drug paraphernalia.

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00:22:07.119 --> 00:22:07.859
No big deal.

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00:22:08.160 --> 00:22:11.930
A minor entry on a criminal record. But it sat

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00:22:12.089 --> 00:22:18.009
beside like a larger picture that her family painted. After

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00:22:18.109 --> 00:22:21.400
all this happened, a young woman who had become chaotic,

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00:22:21.640 --> 00:22:25.019
who was using substances and was under the control of

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00:22:25.099 --> 00:22:28.839
someone who exploited her. And by the time she encountered

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00:22:28.940 --> 00:22:34.140
Aubrey Trail, Bailey Boswell, she was in a vulnerable position.

325
00:22:34.359 --> 00:22:37.960
This girl had experienced the murder of her biological father

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00:22:38.039 --> 00:22:40.859
before she could even form memories of him. She had

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00:22:40.900 --> 00:22:44.380
been sexually assaulted. She had been in a relationship marked

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00:22:44.420 --> 00:22:48.720
by violence and trafficking, and she had lost primary custody

329
00:22:48.759 --> 00:22:52.880
of her child. She was young, financially unstable, and she's

330
00:22:52.960 --> 00:22:58.349
looking for security, right? According to statements made through legal proceedings,

331
00:22:58.730 --> 00:23:02.809
she sought out a path of a sugar daddy through

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00:23:02.829 --> 00:23:06.650
the classified site back page. And this is where the

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00:23:06.750 --> 00:23:11.269
paths of Bailey Boswell and Aubrey Trail would cross.

334
00:23:11.630 --> 00:23:12.450
Trail was older.

335
00:23:12.609 --> 00:23:16.130
He was roughly twice her age, but he presented himself

336
00:23:16.289 --> 00:23:19.730
as a man with money, with connections, and with the

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00:23:19.789 --> 00:23:23.470
ability to provide a different life for her. And he

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00:23:23.599 --> 00:23:29.279
used names and stories that suggested he was this badass.

339
00:23:28.539 --> 00:23:31.559
Guy, right? And to a young woman who had been.

340
00:23:31.460 --> 00:23:34.890
Exploited in trying to find solid ground, it was a

341
00:23:35.089 --> 00:23:38.849
rescue for her. Family members would later say they never

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00:23:38.930 --> 00:23:43.480
had a good feeling about Aubrey Trail. One described him

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00:23:43.559 --> 00:23:47.750
as scum. They noticed the control that Bailey was under,

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00:23:48.190 --> 00:23:52.289
and she would obey just about everything he said. He

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00:23:52.329 --> 00:23:57.200
provided cars for her, housing, money, and in exchange, he

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00:23:57.279 --> 00:24:02.880
expected compliance, check-ins, and the recruitment of young women as

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00:24:02.940 --> 00:24:08.069
he made her rely on this financial dependence. So Bailey

348
00:24:08.150 --> 00:24:11.410
eventually moves in with Trail and they would travel and

349
00:24:11.450 --> 00:24:15.180
they would engage in these antique and coin fraud schemes

350
00:24:15.259 --> 00:24:20.220
that funded their lifestyle. She became the more approachable face

351
00:24:20.460 --> 00:24:24.480
in the recruitment of other women. Trail knew this. He

352
00:24:24.559 --> 00:24:27.000
knew if he had a woman there and he was

353
00:24:27.059 --> 00:24:29.869
trying to recruit other women, it would be easier for

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00:24:30.009 --> 00:24:33.430
her to do that than him. And they would use

355
00:24:33.650 --> 00:24:37.420
Tinder for these recruitments, if you will. So by the

356
00:24:37.500 --> 00:24:41.680
summer and fall of 2017, Aubrey Trail and Bailey Boswell,

357
00:24:41.740 --> 00:24:44.779
they were living together in a basement apartment. This is

358
00:24:44.880 --> 00:24:49.880
in Wilbur, Nebraska. And together they had generated enough income

359
00:24:50.019 --> 00:24:54.900
to support a lifestyle that would include hotel stays, casino visits,

360
00:24:55.259 --> 00:24:58.480
and the ability to offer housing or cash to young

361
00:24:58.559 --> 00:25:01.750
women that they would draw into this circle. Now, one

362
00:25:01.769 --> 00:25:06.490
of the more significant schemes that they did involved defrauding

363
00:25:06.609 --> 00:25:13.859
a Kansas couple of roughly $ 375, 000 cash in gold coins

364
00:25:14.220 --> 00:25:16.240
through a high-value coin deal.

365
00:25:16.759 --> 00:25:17.880
And Trill, it.

366
00:25:17.859 --> 00:25:20.880
Would come out later, used the name Alan Russell in

367
00:25:20.940 --> 00:25:25.210
that operation. So the Wilbur basement where they lived, that

368
00:25:25.279 --> 00:25:29.019
became the physical center of their operation. It was the

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00:25:29.059 --> 00:25:33.559
place where women were brought, where rules were explained, where

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00:25:33.599 --> 00:25:37.759
the couple's particular blend of crime and control would play out.

371
00:25:38.240 --> 00:25:42.380
Trell would position himself as the provider, the authority figure.

372
00:25:42.789 --> 00:25:47.250
He was older, experienced, and he had money. Boswell, closer

373
00:25:47.289 --> 00:25:50.670
in age to the women they recruited and more approachable

374
00:25:50.750 --> 00:25:54.819
on the surface, would serve as that initial point of contact.

375
00:25:55.059 --> 00:25:57.609
And the way they would do this, Boswell would create

376
00:25:57.710 --> 00:26:02.109
profiles on Tinder and similar platforms. She would use aliases

377
00:26:02.210 --> 00:26:06.309
like Audrey, Jenna, and others, and she matched with these

378
00:26:06.410 --> 00:26:11.359
young women. They would engage in flirtatious conversation, and they

379
00:26:11.380 --> 00:26:16.220
would arrange meetings. And once a connection was established, she

380
00:26:16.259 --> 00:26:20.119
would introduce the women to trail. He was framed as

381
00:26:20.200 --> 00:26:23.769
a sugar daddy, and he was the central figure in

382
00:26:23.829 --> 00:26:29.069
a group lifestyle that offered financial support in exchange for

383
00:26:29.289 --> 00:26:34.180
sex and obedience to them. Now, several women testified under

384
00:26:34.420 --> 00:26:37.480
oath about what that lifestyle entailed. One of the most

385
00:26:37.660 --> 00:26:41.240
detailed accounts came from a woman identified in court records

386
00:26:41.319 --> 00:26:45.779
as Ashley Hills. She described meeting Boswell through the dating

387
00:26:45.980 --> 00:26:50.410
app in the summer of 2017 and then being introduced

388
00:26:50.430 --> 00:26:52.910
to Trail. Trail told her he could help her get

389
00:26:53.009 --> 00:26:57.150
revenge on an abusive stepfather. He spoke of a group

390
00:26:57.250 --> 00:27:01.460
of women he called, quote, his girls or witches, and

391
00:27:01.480 --> 00:27:05.500
he claimed that there were others already involved. Boswell was

392
00:27:05.599 --> 00:27:10.710
referred to as the Queen Witch. Trail described himself at

393
00:27:10.829 --> 00:27:15.029
times as a vampire, and he showed Hill's nude photographs

394
00:27:15.150 --> 00:27:18.150
of women that he claimed were part of the group.

395
00:27:18.250 --> 00:27:22.769
The rules, according to testimony, were explicit. Women were expected

396
00:27:22.890 --> 00:27:25.970
to check in every few hours by phone or text.

397
00:27:26.319 --> 00:27:30.339
They needed permission for ordinary activities like eating. They were

398
00:27:30.400 --> 00:27:33.440
not supposed to be involved with other men. And in

399
00:27:33.480 --> 00:27:39.559
the apartment, there were expectations around nudity and sexual availability.

400
00:27:40.099 --> 00:27:44.940
Financial help, including rent, cash, and stability, was the incentive,

401
00:27:45.380 --> 00:27:49.990
and leaving the group was framed as possible until a

402
00:27:50.049 --> 00:27:54.349
certain point. That point, according to what Trail told at

403
00:27:54.430 --> 00:27:59.240
least one woman, involved, quote, taking a soul, which she

404
00:27:59.319 --> 00:28:03.910
understood as killing someone and them taking their last breath. Now,

405
00:28:04.069 --> 00:28:09.339
other women offered overlapping accounts. They described conversations about torture

406
00:28:09.490 --> 00:28:13.440
and recorded acts of violence. About the possibility of selling

407
00:28:13.589 --> 00:28:18.009
videos for large sums of money, one young woman testified

408
00:28:18.130 --> 00:28:21.990
she was told she could become the 13th witch if

409
00:28:22.049 --> 00:28:26.490
she tortured and killed someone. Prosecutors would later argue these

410
00:28:26.609 --> 00:28:31.849
conversations would demonstrate that everything was premeditated and that they

411
00:28:31.890 --> 00:28:36.049
had a genuine interest in violence. The defense for both

412
00:28:36.349 --> 00:28:39.470
Trail and Boswell would characterize much.

413
00:28:39.269 --> 00:28:41.509
Of it as a dark fantasy. They would say this

414
00:28:41.549 --> 00:28:43.910
was role play. It was just talk.

415
00:28:44.309 --> 00:28:48.440
It never crossed into concrete planning until, in fact, the

416
00:28:48.500 --> 00:28:52.359
night that Sidney Loof died. The jury and the sentencing

417
00:28:52.420 --> 00:28:57.579
judges ultimately treated this pattern of related evidence as intent crime.

418
00:28:58.569 --> 00:29:01.349
and spoke to the character of these two. So back

419
00:29:01.390 --> 00:29:05.569
to the night in question. On November 11th of 2017,

420
00:29:05.569 --> 00:29:09.359
Sidney Louf, she matched on Tinder with a woman using

421
00:29:09.420 --> 00:29:13.240
the name Audrey. And the profile presented a young woman

422
00:29:13.440 --> 00:29:17.869
interested in meeting someone. The early messages are everything you thought.

423
00:29:17.940 --> 00:29:21.490
They would talk about food, plans to meet, et cetera.

424
00:29:21.849 --> 00:29:24.730
And Sidney, she was smart enough to ask direct questions,

425
00:29:25.349 --> 00:29:28.069
asking whether it would just be the two of them,

426
00:29:28.569 --> 00:29:31.900
and Audrey would reassure her, yes, just.

427
00:29:31.740 --> 00:29:32.519
The two of us.

428
00:29:32.940 --> 00:29:36.750
And they had friendly conversation. They arranged a first date

429
00:29:36.829 --> 00:29:39.289
for November 14th. Sidney went.

430
00:29:39.470 --> 00:29:40.809
She came home. safely.

431
00:29:40.950 --> 00:29:44.960
Everything was perfect. And afterwards, she even told a friend, hey,

432
00:29:45.000 --> 00:29:48.259
I think I found the one. That second meeting was

433
00:29:48.299 --> 00:29:51.599
scheduled for the 15th. While Sidney was still at work

434
00:29:51.779 --> 00:29:56.039
at Menards in Lincoln that day, Aubrey Trail and Bailey

435
00:29:56.099 --> 00:30:01.130
Boswell were already moving through stores buying shit. Surveillance videos

436
00:30:01.170 --> 00:30:05.430
and receipts would later place them at multiple locations where

437
00:30:05.450 --> 00:30:09.420
they bought a folding saw, a weeder, food grinders. At

438
00:30:09.500 --> 00:30:14.420
Home Depot, they purchased a foot-long hacksaw, wire snips, drop claws,

439
00:30:14.779 --> 00:30:19.109
a sharp utility knife with extra blades. They also purchased

440
00:30:19.250 --> 00:30:23.690
a large quantity of Clorox bleach, 30-gallon trash bags, and

441
00:30:23.829 --> 00:30:27.880
all kinds of related cleaning supplies. And cell phone data

442
00:30:27.930 --> 00:30:31.900
would add another layer. Trell was captured on camera at

443
00:30:31.940 --> 00:30:36.099
the Menards location where Sidney worked. The timing and movement

444
00:30:36.240 --> 00:30:40.420
of the couple's phones were consistent with the awareness of

445
00:30:40.900 --> 00:30:46.339
Sidney's location and schedule. And prosecutors would later call this monitoring.

446
00:30:46.710 --> 00:30:49.589
So Sydney leaves for work that day, she returns to

447
00:30:49.650 --> 00:30:52.589
her apartment, and she prepares for that second date. She

448
00:30:52.630 --> 00:30:55.730
posted that Snapchat story that I told you about where

449
00:30:55.789 --> 00:30:58.829
she said, ready for my date, and her phone activity

450
00:30:58.890 --> 00:31:03.849
showed movements toward the basement apartment Trail and Boswell shared.

451
00:31:04.029 --> 00:31:08.190
The last significant pings occurred in that area around 8.30

452
00:31:08.190 --> 00:31:08.950
that evening.

453
00:31:10.549 --> 00:31:12.170
And then the whole thing goes dark.

454
00:31:12.470 --> 00:31:15.990
Now, what happened inside that apartment is known through primarily

455
00:31:16.089 --> 00:31:21.250
Trail's own shifting statements to investigators. The physical evidence recovered

456
00:31:21.289 --> 00:31:26.039
later and the forensic conclusion drawn from the remains. Trail

457
00:31:26.119 --> 00:31:29.900
admitted in multiple interviews that he strangled Sidney with an

458
00:31:30.000 --> 00:31:33.759
extension cord, and the accounts would vary over time. Some

459
00:31:33.819 --> 00:31:38.289
versions He claimed the death occurred during a consensual sex act.

460
00:31:38.589 --> 00:31:41.910
In others, he said she reacted badly when he revealed

461
00:31:41.950 --> 00:31:45.250
the nature of their relationship and he killed her to

462
00:31:45.349 --> 00:31:48.549
keep her from talking. And in others, he took primary

463
00:31:48.650 --> 00:31:53.970
responsibility while attempting to minimize Boswell's role, depending on who

464
00:31:54.009 --> 00:31:56.779
he was talking to. The guy was absolutely crazy. But

465
00:31:56.940 --> 00:31:58.519
one thing remained consistent.

466
00:31:59.119 --> 00:31:59.759
The method.

467
00:32:00.339 --> 00:32:05.400
Strangulation with an electrical cord. was the way he killed her.

468
00:32:05.750 --> 00:32:08.750
Items were covered near the body and in related searches

469
00:32:09.089 --> 00:32:12.269
added a sexual component to the events in the apartment.

470
00:32:12.650 --> 00:32:16.809
A plastic sauna suit with the crotch cut out, sex toys,

471
00:32:16.950 --> 00:32:21.329
a dog collar, leash, restraints, and other material were found

472
00:32:21.690 --> 00:32:25.609
in the proximity of the remains. Prosecutors were argued these

473
00:32:25.650 --> 00:32:29.099
were elements of part of the crime itself. In the defense,

474
00:32:29.259 --> 00:32:32.390
they would say, There's all kinds of things you can

475
00:32:32.450 --> 00:32:37.210
interpret from that. After the killing would come the dismemberment.

476
00:32:37.569 --> 00:32:41.410
The tools purchased earlier that day, remember the hacksaw, the

477
00:32:41.549 --> 00:32:46.859
utility knives, etc. They were consistent with cuts on the body. Now,

478
00:32:46.990 --> 00:32:55.160
Sidney's remains were separated into approximately 14 pieces. Some internal organs,

479
00:32:55.279 --> 00:32:59.170
including her heart, were never recovered. The pieces were placed

480
00:32:59.509 --> 00:33:02.910
in 30-gallon black trash bags that the couple had bought

481
00:33:03.369 --> 00:33:05.950
in the work. And believe it or not, these animals

482
00:33:05.990 --> 00:33:10.839
had cleaned up so much, the apartment found no blood

483
00:33:10.960 --> 00:33:16.099
evidence despite the nature of these injuries. Prosecutors would say

484
00:33:16.279 --> 00:33:20.039
this is evidence of the planning, the preparation, and the

485
00:33:20.079 --> 00:33:24.190
deliberate cleanup. And I couldn't agree more with that. The

486
00:33:24.230 --> 00:33:28.339
bags were then transported roughly an hour west into rural

487
00:33:28.430 --> 00:33:32.160
Clay County. They were deposited along gravel roads and in

488
00:33:32.279 --> 00:33:36.900
ditches near the town of Edgar, and multiple disposal sites

489
00:33:37.079 --> 00:33:42.200
were later identified, 17 in total according to investigative accounts.

490
00:33:42.619 --> 00:33:47.079
Some bags were torn or partially open when found. Additional

491
00:33:47.220 --> 00:33:52.500
items like tarps with biological material, pieces of the sauna suit, gloves,

492
00:33:52.880 --> 00:33:57.099
clothing fragments, and even the extension cord were recovered in

493
00:33:57.140 --> 00:34:00.200
the same general area. Now, in the hours and days

494
00:34:00.339 --> 00:34:06.079
immediately after this killing, Trell and Boswell did not remain static,

495
00:34:06.180 --> 00:34:09.519
if you will. Cell data and hotel records showed a

496
00:34:09.559 --> 00:34:13.880
lot of movement. They stayed in various locations, including hotels.

497
00:34:14.300 --> 00:34:18.199
They continued some of their ordinary patterns, and they began

498
00:34:18.320 --> 00:34:22.420
constructing what I would call a public narrative. When law

499
00:34:22.440 --> 00:34:26.360
enforcement eventually named them as people of interest, the couple

500
00:34:26.429 --> 00:34:30.750
responded with Facebook Live videos in which they denied involvement,

501
00:34:30.909 --> 00:34:34.190
claimed they had spent time with Cindy, and offered an

502
00:34:34.250 --> 00:34:38.230
account of dropping her off at a friend's house. Those videos,

503
00:34:38.429 --> 00:34:44.510
while attempts at control, ultimately helped investigators locate them. So

504
00:34:44.590 --> 00:34:49.719
as I told you, Sydney gets reported on November 16th, 2017.

505
00:34:49.719 --> 00:34:52.780
And by that evening, her family had filed a missing

506
00:34:52.880 --> 00:34:56.659
persons report with the Lincoln Police Department. Officers would conduct

507
00:34:56.699 --> 00:35:00.639
a welfare check and they would see that her glasses

508
00:35:00.739 --> 00:35:03.710
were there. her purse, all the things you would bring

509
00:35:03.769 --> 00:35:07.570
if you're leaving. But more than anything else, they noticed Mimsy,

510
00:35:07.670 --> 00:35:11.230
her cat, was there without food and water. Everybody knew

511
00:35:11.269 --> 00:35:14.380
there's no way that would have happened. So that scene

512
00:35:14.780 --> 00:35:20.320
would suggest she had left voluntarily, but intended to return soon.

513
00:35:20.539 --> 00:35:25.570
Investigators would reconstruct her last known moments. Friends would identify

514
00:35:25.619 --> 00:35:29.090
that Tinder match. And when police looked into that, they

515
00:35:29.130 --> 00:35:30.789
found a profile named Audrey.

516
00:35:31.260 --> 00:35:32.199
The phone number.

517
00:35:32.039 --> 00:35:36.269
Associated with that account was traced to an application that

518
00:35:36.309 --> 00:35:40.829
was linked to Bailey Boswell, and cell tower data would

519
00:35:41.010 --> 00:35:46.659
quickly focus the attention on Wilbert, Nebraska, and specifically on

520
00:35:46.719 --> 00:35:50.739
that basement apartment. When officers and the landlord went to

521
00:35:50.760 --> 00:35:54.960
the residence, they noted a strong bleach odor, which is

522
00:35:55.000 --> 00:35:58.159
a big red flag. And they also noticed the unusual

523
00:35:58.239 --> 00:36:01.869
fact the air conditioner was running, and this was mid-November

524
00:36:01.929 --> 00:36:04.889
in a very cold area of the country. No way

525
00:36:04.949 --> 00:36:07.630
that would have happened unless it was intentional. So they

526
00:36:07.650 --> 00:36:10.590
get a search warrant, they go into the apartment, and

527
00:36:10.630 --> 00:36:14.559
it appeared too clean. as if someone had cleaned it

528
00:36:14.980 --> 00:36:16.000
to the point you could eat.

529
00:36:15.940 --> 00:36:16.599
Off the floor.

530
00:36:16.960 --> 00:36:20.960
There was no blood evidence or really anything obvious that

531
00:36:21.079 --> 00:36:24.300
that was a crime scene. So they keep investigating. Trail

532
00:36:24.340 --> 00:36:28.090
and Boswell publicly are named as people of interest because

533
00:36:28.110 --> 00:36:31.269
they couldn't locate them and The couple, as I said,

534
00:36:31.429 --> 00:36:36.670
responded on Facebook Live with videos denying any involvement. Police

535
00:36:36.710 --> 00:36:39.510
were able to work with Facebook to figure out where

536
00:36:39.550 --> 00:36:44.409
those videos came from. And on November 30th, 2017, Trail

537
00:36:44.500 --> 00:36:48.699
and Boswell are arrested in Branson, Missouri. They were taken

538
00:36:48.760 --> 00:36:53.280
into custody primarily on federal fraud charges. connected to a

539
00:36:53.340 --> 00:36:56.699
Kansas coin scheme because they didn't have enough evidence to

540
00:36:56.800 --> 00:37:00.239
charge them yet for this. And on them, they have maps,

541
00:37:00.400 --> 00:37:05.679
hiking shoes, and a lot of materials that would suggest

542
00:37:05.699 --> 00:37:09.130
they were not planning to go home anytime soon. Now,

543
00:37:09.170 --> 00:37:13.289
the critical breakthrough on the body came days later. Lincoln

544
00:37:13.349 --> 00:37:17.510
Police Investigator analysis of cell tower data from the night

545
00:37:17.530 --> 00:37:23.269
of November 15th would follow these two down rural roads

546
00:37:23.429 --> 00:37:26.769
in Clay County. When they checked out this data, they

547
00:37:26.809 --> 00:37:31.699
were able to actually almost find exactly where these bags

548
00:37:31.780 --> 00:37:35.940
were based off of that cell tower data.

549
00:37:36.260 --> 00:37:37.480
Now, when they found all of.

550
00:37:37.480 --> 00:37:41.750
This, obviously the case gets transformed from a missing persons

551
00:37:41.809 --> 00:37:47.010
case into homicide. Formal charges of first-degree murder and improper

552
00:37:47.079 --> 00:37:51.340
disposal of human skeletal remains were filed against both Trail

553
00:37:51.440 --> 00:37:55.619
and Boswell. This is in June of 2018. And conspiracy

554
00:37:55.679 --> 00:38:00.130
charges were added... as well. Trell eventually entered a plea

555
00:38:00.250 --> 00:38:04.250
to the improper disposal count and both maintained not guilty

556
00:38:04.309 --> 00:38:09.030
positions on the murder and conspiracy charges. So Aubrey Trell's

557
00:38:09.150 --> 00:38:15.130
trial took place in 2019 and the evidence presented was extensive.

558
00:38:15.610 --> 00:38:18.690
Store surveillance, everything I told you about, the receipts for

559
00:38:18.730 --> 00:38:22.449
the hacksaws, tin snaps, utility knife bleach, all that shit,

560
00:38:22.849 --> 00:38:25.929
cell phone data, that put this guy at the scene.

561
00:38:26.170 --> 00:38:30.199
And Trail's own statements to FBI agents were enough.

562
00:38:30.389 --> 00:38:31.559
He couldn't get out of this.

563
00:38:32.179 --> 00:38:35.420
The jury deliberated for less than three hours, and they

564
00:38:35.500 --> 00:38:40.500
returned guilty verdicts on first-degree murder, conspiracy to commit first-degree murder,

565
00:38:40.800 --> 00:38:44.059
and some related counts. And the moment of the verdict

566
00:38:44.320 --> 00:38:48.949
produced one of the most dramatic scenes in Nebraska courtroom history.

567
00:38:49.550 --> 00:38:50.409
Trail stood.

568
00:38:50.889 --> 00:38:55.380
declared that Bailey Boswell was innocent, cursed the court and

569
00:38:55.440 --> 00:38:58.960
the jury, and then used a small razor blade he

570
00:38:59.000 --> 00:39:02.670
had concealed to slash his own throat right there in

571
00:39:02.730 --> 00:39:03.329
open court.

572
00:39:03.750 --> 00:39:06.809
I bet you didn't expect that. But the wounds were

573
00:39:06.869 --> 00:39:07.530
not fatal.

574
00:39:08.070 --> 00:39:12.440
Medical attention was provided and he survived and later chose

575
00:39:12.659 --> 00:39:18.320
not to attend subsequent proceedings. So Bailey Boswell's trial follows.

576
00:39:18.380 --> 00:39:23.480
This is in 2020. Because of extensive pretrial publicity, the

577
00:39:23.519 --> 00:39:26.690
venue was moved to what's known as Dawson County. The

578
00:39:26.750 --> 00:39:31.110
court evidence mirrored that that was presented in the trail trial.

579
00:39:31.880 --> 00:39:35.079
Everything I already told you about. And of course, Bailey

580
00:39:35.139 --> 00:39:39.280
Boswell is convicted of first degree murder, conspiracy and improper

581
00:39:39.320 --> 00:39:44.139
disposal of human remains and sentencing upcoming. Now, something to

582
00:39:44.199 --> 00:39:48.360
say about sentencing. In Nebraska, capital cases are actually handled

583
00:39:48.400 --> 00:39:52.239
by a three judge panel rather than a trial jury.

584
00:39:52.639 --> 00:39:56.699
And that panel must be unanimous in finding an aggravating

585
00:39:56.780 --> 00:40:01.210
circumstance has been proven beyond a reasonable doubt. before the

586
00:40:01.289 --> 00:40:05.610
death sentence can get imposed. In June 2021, the panel

587
00:40:05.650 --> 00:40:11.829
considered Aubrey Trail's sentence and found the aggravating circumstances unanimously

588
00:40:11.989 --> 00:40:16.699
were proven, and Judge Vicki Johnson, who spoke for the panel,

589
00:40:16.780 --> 00:40:21.539
described the crime as involving cold, calculated planning. She noted

590
00:40:21.579 --> 00:40:26.679
that Sidney had been selected, lured, killed, and needlessly mutilated

591
00:40:27.059 --> 00:40:29.630
in a manner that went beyond what was required to

592
00:40:29.750 --> 00:40:34.829
just conceal a body. The judges concluded the manipulation served

593
00:40:35.070 --> 00:40:39.610
both intellectual and sexual purposes, and he was sentenced to death.

594
00:40:40.010 --> 00:40:43.349
Bailey Boswell's sentence hearing was held in November of 2021.

595
00:40:43.349 --> 00:40:49.219
Two of three judges found the stated proven exceptional depravity.

596
00:40:49.639 --> 00:40:52.320
They pointed to the planning, the luring of the victim,

597
00:40:52.760 --> 00:40:56.869
participating in the killing and the needless mutilation. The third

598
00:40:56.929 --> 00:41:01.289
judge did not join that finding. And because the law

599
00:41:01.309 --> 00:41:04.980
in Nebraska must be unanimous for a death sentence, Bailey

600
00:41:05.039 --> 00:41:09.780
Boswell ended up with life in prison without the possibility

601
00:41:09.820 --> 00:41:10.480
of parole.

602
00:41:10.840 --> 00:41:16.030
Of course, appeals would follow. However, all of those were denied.

603
00:41:16.139 --> 00:41:19.449
And as of 2026, as it relates to Aubrey Trail,

604
00:41:19.650 --> 00:41:24.710
he's still on death row. He's at Tecumseh State Correctional Institution.

605
00:41:25.190 --> 00:41:27.150
Still doesn't have an execution date.

606
00:41:27.630 --> 00:41:29.389
And Boswell, her.

607
00:41:29.309 --> 00:41:33.809
Life sentences also unanimously upheld. And she is serving her

608
00:41:33.869 --> 00:41:38.250
sentence at Nebraska Correctional Center for Women in York. Now,

609
00:41:38.329 --> 00:41:42.599
for Sidney's family, that legal process... Brought a.

610
00:41:42.659 --> 00:41:46.159
Measure of finality. Of course, you never get closure.

611
00:41:46.719 --> 00:41:51.380
You can get justice to some extent. George and Susie Loof,

612
00:41:51.539 --> 00:41:55.380
along with her siblings Levi and Mackenzie, they sat through

613
00:41:55.440 --> 00:41:59.280
all this horrificness of these trials. Just a horrific crime.

614
00:41:59.659 --> 00:42:03.539
that I brought you today, certainly fitting of 50 shades

615
00:42:03.679 --> 00:42:06.619
of evil. And in this new world that we live

616
00:42:06.679 --> 00:42:09.619
in now, where people don't date like they used to,

617
00:42:09.639 --> 00:42:12.840
you meet people on dating apps. You absolutely don't know

618
00:42:12.920 --> 00:42:16.239
somebody on a dating app. I can't believe that people

619
00:42:16.320 --> 00:42:19.460
focus so much on that. Whatever happened to meeting, you know,

620
00:42:20.260 --> 00:42:22.719
you got five friends and you're all out dancing or

621
00:42:22.760 --> 00:42:24.059
something and you meet somebody.

622
00:42:23.820 --> 00:42:26.559
Or maybe you meet him at church, whatever. This is

623
00:42:26.599 --> 00:42:27.519
how they do it now.

624
00:42:27.780 --> 00:42:31.480
And it is extremely dangerous, as you can see, and

625
00:42:31.519 --> 00:42:33.719
I'm sure you already know. But there you have it.

626
00:42:33.820 --> 00:42:37.460
Cindy Loof, 24 years old, loved fishing, loved her cat,

627
00:42:37.480 --> 00:42:40.650
showed up for work, helped other people that were struggling,

628
00:42:41.130 --> 00:42:44.469
and was trying, even in the middle of her own difficulties,

629
00:42:44.690 --> 00:42:47.389
to find a connection with somebody. On the night of

630
00:42:47.469 --> 00:42:53.130
November 15th, 2017, that search ended in a basement apartment

631
00:42:53.260 --> 00:42:57.559
in Wilbur, at the hands of two people who had

632
00:42:57.619 --> 00:43:00.920
plans from the beginning to kill her. So my thoughts

633
00:43:01.119 --> 00:43:05.260
obviously go out to her family and my prayers for

634
00:43:05.320 --> 00:43:07.929
what they've been through. I'll be back next week with

635
00:43:07.989 --> 00:43:11.929
another episode. And until next time, for Bloody Angola, I'm

636
00:43:11.949 --> 00:43:13.090
your host, Jim Chapman.

637
00:43:13.650 --> 00:43:14.250
Much love.