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Sydney Loofe thought she was heading out for a second date with a woman she met on Tinder. Instead, the 24-year-old vanished — and the man convicted of her murder would later make a disturbing admission about why she proved to be the “wrong person” to kill.
“I don’t regret killing Sydney,” Aubrey Trail said, according to filmmaker Christopher St. John. “I don’t regret killing somebody, but I regret killing … I picked the wrong person.”
Trail, then a 52-year-old con man, was convicted of strangling the Nebraska store clerk with an electrical cord in 2017, cutting her body into 14 pieces, placing the remains in garbage bags and dumping them in roadside ditches. At the trial, witnesses testified that Trail and his girlfriend, Bailey Boswell, then 25, had solicited them for group sex and talked about the occult and gaining “powers” through killing.
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Aubrey Trail, 60, remains on death row at the Tecumseh State Correctional Institution in Nebraska. He was sentenced to death in 2021 for the 2017 murder of 24-year-old Sydney Loofe. According to “Swipe Right on the Devil,” Trail and his girlfriend, Bailey Boswell, used the dating app Tinder to lure victims. (Hulu)
“One of the FBI agents said that the culprits were in a frenzy,” St. John told Fox News Digital. “They were looking to do this, and Sydney was the available target. She was trusting and innocent and fit the profile. You then later hear Aubrey Trail, the murderer, says, ‘I picked the wrong person.'”
“I think that’s incredibly chilling for me because he has no remorse, but he wishes that he hadn’t chosen someone with such strong family and friends because it led to his capture.”
“Swipe Right on the Devil,” the three-part true crime docuseries about Sydney Loofe’s murder, is streaming now on Hulu. (Hulu)
Loofe’s murder at the hands of Trail, who described himself as a “powerful warlock” and the leader of a sex cult, is explored in the new Hulu true crime docuseries “Swipe Right on the Devil.” The three-part series features interviews with Loofe’s loved ones and investigators, as well as recordings of Trail from death row.
Sydney Loofe went on a date before she vanished. (FBI Omaha)
Loofe, a cashier at Menards, a home improvement store, lived alone in an apartment with her cat, Mimsy. According to friends, she was yearning for a relationship. On Tinder, she came across a profile for a woman named Audrey, an alias used by Boswell. After matching and exchanging messages, the two women went on their first date. They planned a second date for the next day. Loofe was smitten.
“Sydney was like any one of us,” said St. John. “She was feeling lonely and searching for belonging. She had gone on a date with this woman, and she was so excited that she immediately wrote to her friends. They were like, ‘Great, nothing to worry about.’ And she was never heard from again. Something awful came out of the darkness.”
Sydney Loofe, a 24-year-old Nebraska store clerk, was looking for love when she connected with Bailey Boswell on Tinder in November 2017. What began as a promising match would ultimately lead to her murder. (Lincoln Police Department)
When Loofe didn’t show up for her morning shift the following day, her family requested a welfare check. Police found her car in the driveway. Her work clothes and purse were laid out for work. Her cat hadn’t been fed.
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Sydney Loofe, 24, was reported missing in mid-November 2017. (FBI Omaha)
Loofe’s friend, Brooklyn McCrystal, knew that she had been on a date the night before she disappeared. McCrystal created a Tinder profile to find Audrey in hopes of getting her contact information. When McCrystal matched with Audrey on the dating app, they exchanged phone numbers. McCrystal gave Boswell’s information to police. Loofe’s friends also showed investigators her final social media post, a selfie shared on Snapchat captioned “Ready for my date.”
“Brooklyn provided the first big break in the case,” said St. John. “She catfished the bad guys. There’s digital tracking. It’s got all the hallmarks of an amazing investigation. But ultimately, what led to Aubrey and Bailey’s capture was the people who were devoted to Sydney searching for answers.”
Corey O’Brien of the Nebraska Attorney General’s Office speaks to the media following the first appearance by Aubrey Trail and Bailey Boswell after the pair were charged with first-degree murder of Sydney Loofe and improper disposal of human skeletal remains at the Saline County Courthouse in Wilber, Nebraska, June 12, 2018. (Omaha World-Herald via Getty Images)
Boswell refused to cooperate with investigators. When police tracked her phone, they learned it was a burner phone registered under a fake name. They traced the phone to hotels in the area, where surveillance video and a state-issued ID presented at check-in helped investigators identify Boswell as “Audrey.” The video also showed that she was traveling with an older man, Trail. The Lincoln Journal Star reported that Loofe’s phone last pinged at Boswell and Trail’s apartment that night.
Bailey Boswell and Aubrey Trail were a couple living together in Wilber, Nebraska, when they were accused of luring women through dating apps and drawing them into a controlling relationship involving sex, crime and claims of witchcraft. Both were later convicted in the 2017 murder of Sydney Loofe. (Hulu)
Investigators obtained a search warrant for the apartment, which smelled strongly of bleach. Boswell and Trail had paid their rent early and left.
Police named Boswell and Trail as persons of interest. On Nov. 29, 2017, the couple released a video on social media denying any involvement in Loofe’s disappearance. Boswell said she had gone on two dates with Loofe, but after their second date, she had dropped Loofe off at a friend’s house. Despite maintaining their innocence, they went on the run.
Sydney Loofe was last seen alive on Nov. 15, 2017, when she left for a second date with Bailey Boswell, whom she had met on Tinder. Prosecutors said Boswell took the 24-year-old to the Nebraska apartment she shared with Aubrey Trail, where Loofe was murdered. (FBI Omaha)
Boswell and Trail were arrested on Nov. 30, 2017, near Branson, Missouri, on unrelated federal fraud charges.
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Aubrey Trail and Bailey Boswell were arrested in Missouri on Nov. 30, 2017, on unrelated warrants as authorities investigated the disappearance of Sydney Loofe. The couple was formally charged with first-degree murder in Loofe’s death in June 2018. (Saline County Sheriff’s Office)
Nearly three weeks after Loofe disappeared, investigators used cellphone data to trace Boswell and Trail’s movements and identify rural areas where they appeared to have slowed down or stopped.
On Dec. 4, 2017, investigators searched a roadside ditch near Edgar, Nebraska. They found car keys, a phone, a label with Loofe’s name and her dismembered upper arm, which bore a tattoo that read “Everything will be wonderful someday.” The Lincoln Journal Star reported that some garbage bags contained her clothing.
Sydney Loofe had a tattoo on her left forearm that read, “Everything will be wonderful someday.” The deeply personal message became a poignant reminder of the 24-year-old’s hopeful outlook on life following her 2017 murder. (Hulu)
According to court documents, Trail and Boswell were captured on surveillance video at a Home Depot in Lincoln on Nov. 15, 2017, buying tools investigators believed were used to dismember Loofe, hours before her death. Investigators believed Boswell and Trail had lured Loofe through Tinder before killing her and dismembering her body.
Bailey Boswell appears via video conference during her first court appearance before Saline County Judge Linda Bauer after being charged with first-degree murder in the death of Sydney Loofe and improper disposal of human skeletal remains at the Saline County Courthouse in Wilber, Nebraska, on June 12, 2018. (Omaha World-Herald via Getty Images)
“During the trial, the prosecutor said that Aubrey and Bailey had four arms, four legs and one mind,” director Brian Biegel told Fox News Digital. “That speaks to how intertwined they were, how they fed off of each other’s darkness and desire for evil.”
After his arrest, investigators questioned Trail about accounts that he portrayed himself as a powerful warlock and surrounded himself with women he called witches. Trail initially dismissed the occult talk as role-playing, but later told investigators, “Witches kill … the more they kill, their power increases.”
“I spoke to Aubrey Trail for over two years on the telephone and on video conferences,” said Biegel. “I do believe that he believes, based on his history growing up in rural Tennessee and the people that he was groomed by, which, according to him, were witches and they believe in dark magic.”
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Aubrey Trail is seen here being interrogated by investigators. (Hulu)
“I believe, that he believes, that he has special powers and he can use them mostly to manipulate vulnerable people into bending to his will,” Biegel continued. “And I think that’s an important distinction because yes, in his words, he was trying to form a coven of witches and groom them to do awful, terrible things. It’s his belief that if they had done that, they would have superpowers.”
St. John said the filmmakers were aware during production that Trail was “a liar and a serial one.”
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Prosecutors said Aubrey Trail strangled Sydney Loofe with an electrical cord and cut her body into 14 pieces, which he then dumped in various ditches along the sides of rural roads in Nebraska. (Nebraska Department of Corrections)
“There’s truth in and among the lies, so we were constantly trying to check ourselves and be like, ‘Are we being manipulated by him just like he manipulated these young women?’ And honestly, we didn’t want to give him more of a platform for his, frankly, out-there views.”
The docuseries also examines how Boswell used multiple identities on Tinder to meet women, including Loofe.
Ana Golyakova said Trail required her and Boswell to be intimate in front of him, while Ashley Hills said Trail beat her if she disobeyed his demands. Hills said Trail’s rules included remaining naked, asking permission to do virtually anything — even to use the bathroom — and not speaking to other men.
Bailey Boswell walks out of the courtroom after being sentenced to life in prison without parole for the 2017 murder of Sydney Loofe on Nov. 8, 2021, in Wilber, Nebraska. (Justin Wan/Lincoln Journal Star via AP)
Several women described similar patterns of control. Hills also said Trail told her he practiced witchcraft and could control people’s minds.
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The filmmakers said the women’s accounts were crucial to understanding how Trail and Boswell operated — and how investigators ultimately brought them to justice.
Sydney Loofe’s family and friends played a key role in the investigation after the 24-year-old disappeared in November 2017. Her best friend, Brooklyn McCrystal, created a Tinder profile to track down Loofe’s date, known as “Audrey,” obtained her phone number and turned it over to police. Investigators ultimately identified “Audrey” as Bailey Boswell. (Hulu)
“At the heart of this story is Sydney Loofe and the women who were pulled into the orbit of Aubrey and Bailey,” said St. John.
“These were young women who, in a very universal way, were searching for belonging in a place that was hard for them to find that. It made them vulnerable and, as a result, they fell into this awful situation. But they were incredibly brave. Other than Sydney, who unfortunately was killed, these young women have told their story in court, and they’re responsible for putting these people away.”
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Aubrey Trail appears via video conference during his first court appearance before Saline County Judge Linda Bauer at the Saline County Courthouse on June 12, 2018, in Wilber, Nebraska. (Rebecca S. Gratz/The World Herald via AP)
Trail was convicted of first-degree murder and conspiracy to commit first-degree murder in 2019. He also pleaded no contest to improper disposal of human skeletal remains. He was sentenced to death in 2021.
Boswell was convicted of first-degree murder, conspiracy to commit first-degree murder and improper disposal of human skeletal remains in 2020. She was sentenced to life in prison the following year.
“There was a thirst for doing something really awful to someone that had built up in Bailey and Aubrey’s orbit,” said Biegel. “And so, Sydney was at the wrong place at the wrong time. She came into their world at a time when they were ready to perform some of their supposed beliefs in witchcraft and dark magic.”
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Sydney Loofe was murdered on Nov. 15, 2017, the night she went on a second date with Bailey Boswell. Her remains were discovered on Dec. 4, 2017, in rural Clay County, Nebraska. (Hulu)
“This is obviously a cautionary tale about not knowing who’s on the other side of the screen,” Biegel said. “But had it not been for the brilliant work of the Lincoln Police Department and the FBI, there would probably still be two killers on the streets. Who knows how many other people they would have killed?”
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Fox News Digital’s Michael Ruiz and The Associated Press contributed to this report.
