The Bizarre Disappearance and Murder of Sydney Loofe
When 24-year-old Sydney Loofe didn’t show up for her work shift the morning of Nov. 16, 2017, her co-workers knew something had to be wrong. Normally Loofe was a dependable, responsible woman. When she didn’t answer phone calls or messages from her friends and family, they immediately called the Lincoln, Nebraska, police.
Police went to her home, but nothing seemed out of place, and there was no sign of a struggle.
Next, they looked at her digital records. The last thing she posted online was a selfie with the caption, “Ready for my date.”
Further digging revealed that she had been messaging a woman she’d met on Tinder who went by the name “Audrey.” They had met for a date once before, and were planning on meeting up again the night of Nov. 15.
As the days ticked by, Loofe’s parents went on the media begging for anyone with any information to come forward. Her friends set up a Facebook page to help in the search.
Soon, the FBI got involved. They obtained more of Loofe’s cell phone data, which showed that her phone last pinged about 40 miles south of Lincoln, in a small town called Wilber. Specifically, at the apartment of a couple named Bailey Boswell, 23, and Aubrey Trail, 51.
Boswell and Trail had an extensive criminal history: hot checks, theft, and various other scams, mostly targeting antiques businesses, across multiple states. But nothing violent.
When police went to Boswell and Trail’s apartment to question them, the couple were nowhere to be found. The landlord, however, pointed out that the apartment had smelled strongly of bleach.
So the police obtained a search warrant.
Inside the basement apartment, the smell of bleach was still overpowering. One room had been meticulously cleaned and the walls scrubbed, while the rest of the apartment was cluttered and dirty. It looked as though the couple had left in a hurry.
They also found items that rang their alarm bells: a dog leash (the couple didn’t own a dog), duct tape, a sauna suit with the crotch cut out, zip ties, a hatchet, a plastic drop cloth smeared with blood, and a book on anatomy.
Fearing the worst, the police began searching the rural areas and ponds in and around Wilber. Loofe’s parents continued speaking with the media, trying to keep her case in the public eye.
Then videos of Boswell and Trail began surfacing on social media. In these videos, the couple protested their innocence. Boswell — wearing a black hoodie and large sunglasses — said that she had smoked pot and done other drugs with Loofe on their date, but then dropped her off at a friend’s house afterwards. Trail — his face fully visible — admitted to being a thief, but swore he was not a murderer. They claimed they weren’t running or hiding, but that they couldn’t go home because the local media had prejudiced everyone against them.
Using subpoenaed cell-phone data, police were able to trace the couple’s movements across several states, and saw that they ended up in Branson, Missouri. That’s where their past caught up with them: they were arrested on a previous warrant for stealing several gold coins, then transporting them across state lines.
Now with the couple in custody, the case could move forward. But no one could have expected where it would eventually end up.
Sydney is found…but more questions remain
Boswell’s cell-phone data did more than just reveal where the couple were. It also revealed that on the day Loofe was reported missing, Boswell had driven around 200 miles on various dirt roads in rural Clay County, Nebraska.
When investigators followed the digital trail, they soon found what they were looking for. In a ditch beside an isolated dirt road, investigators noticed a human arm sticking out of a garbage bag. Further searching found more human remains — in 13 separate garbage bags, all near the roads Boswell’s phone had pinged from.
The remains were identified as Loofe’s by her distinctive tattoos.
However, not all of Loofe’s remains were recovered. Her left upper arm was never recovered, and there were no internal organs found, either. What they did find was a latex glove smeared in blood with some of the remains.
An autopsy would reveal that Loofe’s cause of death was suffocation, and that she had bruising that indicated she had fought with her attacker.
Trail immediately confessed. He told police that he and Loofe — along with two other women, but not Boswell — had engaged in some consensual BDSM, which the women had paid him $15,000 to film. He said that during that, he had strangled her with an extension cord solely as an erotic act, but that it “got out of hand” and he accidentally killed her. Afterwards, he said, he panicked and chopped up her body and hid it so as not to get caught.
He was adamant that Boswell was in no way involved with Loofe’s death, and had only helped him dispose of her body.
Boswell corroborated his story, claiming she had fallen asleep in the living room while Loofe, Trail, and the other two women engaged in group sex in the bedroom.
However, the story that Loofe’s death was merely an accident during otherwise consensual sex did not line up with the evidence. First, there were the text messages between Loofe and Boswell. In none of these messages did Boswell mention Trail or any man, leading Loofe to believe the date would just be the two of them.
Investigators also said there was no evidence that anyone other than Loofe, Boswell, and Trail were in the apartment at the time of Loofe’s murder.
Perhaps most damning, surveillance footage from a local Home Depot showed Trail and Boswell, just hours before the “date,” purchasing a hacksaw, tin snips, a utility knife, and plastic drop cloths.
They were extradited back to Nebraska, and each of them was charged with first degree murder, conspiracy to commit murder, and improper disposal of human remains. Trail pled guilty to improper disposal of human remains, but not guilty to the other two counts. Boswell pled not guilty to all three charges against her.
While they were in jail awaiting their trials, authorities discovered coded messages the couple had been exchanging in order to line up their stories. In the messages, Trail insisted on taking all the blame, and said it was important that Boswell be painted as “the victim.”
The two were tried separately, beginning with Trail.
The Trail trial gets even weirder
In June 2019, Trail stood trial for first degree murder and conspiracy to commit murder. In addition to the digital and forensic evidence, the prosecution also had witness testimonies from three women who were ordered to remain anonymous. Their testimonies were used to prove that not only was Loofe’s murder premeditated, but that Trail’s motive was beyond bizarre.
The women — all in their early 20s — testified that they had first met Boswell through Tinder, and that later, Boswell had introduced them to Trail, whom she described as her boyfriend and sugar daddy.
They described being given manicures, expensive clothes, cell phones, drugs, and weekly “allowances” of $150 — $200.
In exchange, the women testified, they were expected to engage in group sex with Trail and Boswell, whom they had to refer to as “Daddy” and “Mommy.” They were also expected to help Trail and Boswell carry out their scams and fence stolen property.
As time went on, the rules of their relationships began to get more controlling: they were forbidden to be with any other men, had to ask permission to do anything, were locked inside the couple’s home or a motel room, and were expected to check in via text or phone every three hours.
But that was only the beginning. The women all testified that Trail described himself as a vampire, and that they were now “witches” who belonged to his cult. They said he claimed to have supernatural powers, like being able to fly and read minds.
The women said that Trail told them they needed to torture and kill someone in order to gain more power — and that he could film it, sell the footage for $1 million, and split the money equally among them. Trail even suggested who to take as victims.
The women said they left the cult by November 2017, before Boswell lured Loofe in. One of them said Boswell had called her later that month, after Loofe’s murder, and convinced her to travel with them to a casino. She said she got a “weird vibe” from them at that time, and once she saw that the Lincoln police were trying to contact them, she left.
Though they all said that Trail had spoken frequently about killing and dismembering someone, none of the women said they had seen Boswell or Trail kill anyone.
At this point, the trial took yet another bizarre detour. While one of the witnesses was taking the stand, Trail stood up in court, yelled, “Sydney is innocent! I curse you all!” and slit his throat with an improvised blade. He was immediately taken out of the courtroom and into an ambulance.
Trail survived his apparent suicide attempt, and his trial continued.
Once he had recovered and was back in the courtroom, he had yet another surprise up his sleeve: he recanted his previous statements, calling them “bullshit.” He said, “There’s no video, there’s no sexual fantasy, there’s no two other people in the room.” He still maintained that he had only accidentally killed Loofe: “I used people for money, I used people for sex … (killing someone) was counterproductive.”
During his trial, FBI agents testified that when the couple were in the Saline County jail awaiting trial, they had passed encoded notes to coordinate their stories.
The trial lasted three weeks — during which time, Trail suffered two heart attacks and a stroke — but in the end, the jury returned a verdict of guilty on all counts. On June 9, 2021, Trail was sentenced to death.
Boswell stood trial in September 2020. Her trial was much less dramatic, but there was also more physical evidence against her, including her DNA on a latex glove found with Loofe’s remains. In October, she was found guilty on all three counts. Her sentencing hearing began July 1, 2021, with her defense arguing that Boswell’s past history of sexual and physical abuse made her “the perfect victim” of Trail, and that she should not receive the death penalty.
On the final day of her sentencing hearing, a tearful Boswell begged the court not to sentence her to death for the sake of her daughter. The court’s decision won’t be made public until, likely, late August. If Boswell is given the death penalty, she will be the first woman in Nebraska to be sentenced to death.
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