What Happened to Sydney Loofe? Inside Her Murder Case

In November 2017, Sydney Loofe went on a Tinder date that led to her murder.

The tragic events began when 24-year-old Loofe met 23-year-old Bailey Boswell online. Boswell, who was operating on the app under the alias “Audrey,” set up a first date with Loofe on November 14, 2017, assuring her that the two of them would be alone. According to police, the two drove around, chatting and smoking marijuana.

But after Loofe and Boswell planned a second date for the very next night, Boswell and her boyfriend—51-year-old Aubrey Trail—began plotting Loofe’s murder. New Hulu docuseries Swipe Right on the Devil explores the case and whether witchcraft played a role in Loofe's killing.

According to FBI testimony given at trial, Boswell and Trail wasted very little time in preparing to kill Loofe. FBI Agent Mike Maseth stated, per Nebraska Public Media, that while Loofe worked her shift as a clerk at a local Menards home improvement store on November 15, 2017, Boswell and Trail went to a different home improvement store to purchase implements used in the murder, including a hacksaw, tin snips and a utility knife.

Maseth further explained that on the afternoon of November 15, Boswell reached out to Loofe on Tinder, sending her a seemingly innocuous message asking how her day was going. But as she sent that message, security footage and cell phone records revealed that Boswell and Trail were actually in the parking lot of Loofe’s workplace—without her knowledge.

That night, Boswell picked up Loofe and took her back to the basement apartment she shared with Trail in Wilber, Neb. Loofe’s phone stopped transmitting thereafter; she was murdered later that evening.

When Loofe missed her next work shift on the morning of November 16, 2017, her mother, Susie Loofe, reported her missing. Nebraska’s Lincoln Police Department conducted a welfare check that evening. They found Loofe’s car and her purse, but not her wallet, keys or cell phone. A ping of Loofe’s phone showed police that its last known location was in Wilber. When her family said she had no ties to the city, authorities began to investigate.

Friends came forward with knowledge of Loofe’s planned Tinder date, leading Boswell and Trail to become persons of interest on November 28. The next day, the duo went on social media to publicly proclaim their innocence, with Boswell claiming she had dropped Loofe off at a friend’s house.

“I’m truly sorry,” she stated in the video. “I didn’t have anything to do with this. I hope Sydney is found, too.”

But in a subsequent video, she and Trail went from denying involvement in Loofe’s death to declaring they would surrender to authorities. They were taken into custody on November 30, 2017, outside Branson, Mo., on unrelated federal fraud charges before being charged with premeditated first-degree murder, conspiracy to commit first-degree murder and improper disposal of human skeletal remains in Loofe’s killing.

Loofe’s remains were located on December 4 and 5 alongside a road in the town of Edgar, Neb., roughly an hour west of Wilber. A forensic pathologist testified that Loofe’s body had been dismembered into 14 pieces, but that multiple pieces—including several organs, such as the heart—were missing. The pathologist determined the cause of death was homicidal violence by strangulation. Loofe was then dismembered, her remains disposed of in garbage bags.

People who knew Boswell in her hometown of Leon, Iowa, told the Omaha World-Herald that she had been a successful student-athlete whose life took a turn for the worse. Boswell alleged in February 2016 she was being emotionally and physically abused by the father of her child, and she sought a protective order. In April 2016, she was arrested for possession of marijuana and use of drug paraphernalia.

A year later, Boswell had fallen in with the 51-year-old Trail, who, according to the Omaha World-Herald, once presented himself as Boswell’s father rather than her boyfriend. Trail had an extensive criminal history, including two prison sentences.

In April 2017, he and Boswell used a bad check to obtain $28,000 of gold and silver coins at a Pennsylvania antiques auction. When they were arrested in Branson in November, they were initially charged with transporting stolen merchandise across state lines.

In June 2018, Boswell and Trail were each charged with first-degree murder and improper disposal of human remains in the death of Sydney Loofe. They pleaded not guilty to both charges. In August, prosecutors added an additional charge of conspiracy to commit murder. By June 2019, Trail changed his plea to no contest solely on the improper disposal of human remains charge. Boswell pleaded not gulty.

Trail and Boswell were tried separately.

Before being tried for Loofe’s murder, Trail confessed to accidentally killing Loofe and claimed he acted alone. Trail spoke with the Omaha World-Herald via phone multiple times from prison saying that Boswell was under the influence of drugs and not present when Loofe died. Instead, he claimed that Loofe was a willing participant in sexual activity with him and two other women when she was accidentally suffocated.

“It wasn’t meant that she was to die,” Trail insisted, further adding that “I should be put to death.” He attempted to follow through on his words in June 2019 when he slashed his neck with a small blade while in court.

However, he changed his story multiple times. Taking the stand in July 2019 after his self-harm attempt, Trail testified, “There’s no video, there’s no sexual fantasy, there’s no two other people in the room.” He also claimed that the discussion of torture and murder was simply talk amongst what he said was a “group” of young women he and Boswell were involved with.

During court proceedings, three other women testified to also having been in Tinder relationships with Boswell and Trail prior to Loofe’s death. Ashley Hills, Anastasia Golyakova and Kaitlyn Brandle alleged that the couple wanted them to torture and kill someone, that Boswell had previously spoken about dismembering a body and wanted to talk about torture during sex, and that Trail claimed he had supernatural powers.

One of the women testified that Trail referred to himself as a “vampire” who had powers to fly and read people’s minds. She said that “he explained that they were witches and everyone had their own roles to play in the cult.” Boswell, the woman testified, was known as the “queen witch.”

But to become one of the “witches,” the witness claimed, Trail informed her that she needed to kill someone—and that she would gain further powers if the victim was tortured first.

Maseth testified that the FBI found a list of 12 or 13 women in Boswell’s purse that noted the “special powers” of each woman.

Maseth also testified that Trail sent Boswell coded letters while they were in jail, plotting out a story about her being an unwilling participant in Loofe’s murder.

However, jurors disagreed.

It took less than three hours for Trail to be convicted of first-degree murder and conspiracy to commit murder in the death of Sydney Loofe. He sought a new trial but was denied, and in June 2021, he was sentenced to death. Trail is currently on death row at Tecumseh State Correctional Institution in Nebraska after unsuccessfully trying to appeal his death sentence in 2025.

Boswell was also eligible for the death penalty following her conviction on the same charges. She would have been the first woman to be sent to death row in Nebraska, but the three-judge panel could not reach the unanimous vote needed for a death sentence. Two judges voted for death and one dissented, resulting in Boswell receiving life in prison in November 2021.

Boswell is serving her sentence at the Nebraska Correctional Center for Women. She also tried to appeal, challenging the admissibility of photos of Loofe’s dismembered body, as well as the testimony of Hills, Golyakova and Brandle. However, the Nebraska Supreme Court ruled unanimously in 2024 to reject her appeal with Justice Stephanie Stacy writing that Boswell’s claims had “no merit.”