Suvechha Sarkar
In November 2017, 24-year-old Sydney Irene Loofe was reported missing in Lincoln, Nebraska, after she failed to show up for work. Soon, the investigation led authorities to her Tinder date, Bailey Marie Boswell. The focus also shifted to Bailey’s boyfriend, Aubrey Clifton Trail, as officials continued digging deeper. Hulu’s ‘Swipe Right on the Devil’ sheds light on the circumstances surrounding the crime and the evidence that led to the conviction of the killers. It also features multiple in-depth interviews with law enforcement officials and the defense attorney who worked on the case.
Bailey Boswell Matched With Sydney Loofe on Tinder Under a Different Name
On February 26, 1994, Priscilla Boswell and her partner gave birth to their daughter in rural Leon, Iowa. Tragedy struck the family when her father was killed when she was just 1 year old. Over time, her mother found love again and married Jeff Boswell. Subsequently, Bailey was adopted by her stepfather. She began focusing on her studies at Central Decatur High School, where she played basketball before graduating. Reports state that she then received a basketball scholarship to attend AIB Business School, but she faced personal difficulties there. Court records specify that Priscilla claimed Bailey was sexually assaulted after meeting a man named Freddy. Bailey later entered into a relationship with him, leading to the birth of their daughter.
Priscilla further alleged in court that Freddy physically and verbally abused Bailey. Gradually, she crossed paths with a man named Aubrey Clifton Trail on Backpage. In one of his interviews, Aubrey claimed that one night Bailey had asked him to save her, prompting him to pick her up. Following that, they got into a relationship and began selling goods at the local antiques market. On November 13, 2017, Bailey used the name of “Audrey” and matched with a 24-year-old woman, Sydney Irene Loofe, in Lincoln, Nebraska. The following day, they went on their first date and decided to have a second date on November 15. Things changed on November 16 when Sydney’s loved ones were unable to contact her and reported her missing.
According to official reports, one of Sydney’s friends also matched with Bailey on Tinder, obtained her number, and then gave it to the police. Experts tracked the phone number to a hotel in Lincoln, where CCTV captured her with Aubrey. In the meantime, investigators tracked down their basement home. Investigative records suggest that the homeowner’s wife reported smelling a strong smell of bleach in the basement shortly after Sydney went missing. Bailey and Aubrey went live on social media in late November 2017, during which they insisted that they didn’t know about the 24-year-old’s whereabouts. Through that live social media stream, digital experts were able to track the IP address.
Mounting Pieces of Evidence Led to the Arrests of Bailey Boswell and Aubrey Trail
Ultimately, the tracking of the IP address helped authorities take Bailey and Aubrey into custody just outside Branson, Missouri, on November 30, 2017. They were initially arrested on some unrelated federal fraud charges. As the investigation continued, officials discovered surveillance footage from the Menards store where Sydney worked. It dated back to November 15, 2017, and captured Bailey waiting in the parking lot while Aubrey went inside to buy some items. In the footage, he passed by Sydney, but the 24-year-old didn’t recognize him.
Eventually, Bailey and Aubrey visited another store, where they bought items such as tin snips and a knife. When officials questioned her, she denied any involvement and asked for an attorney. Upon further expert examination of the phone records of Bailey and Aubrey, it led to the discovery of Sydney’s dismembered remains in early December 2017. On the other hand, Aubrey confessed to the murder but claimed that it happened during a consensual sexual encounter that involved asphyxiation.
According to the detectives on the show, several witnesses, including Ashley Hills, Katie Brandle, and Jaya “Ana” Golyakova, came forward to report that Bailey and her boyfriend had been connecting with women on Tinder to build a “coven” of “witches.” According to Ashley and Katie’s interviews on the show, they alleged that Aubrey and his girlfriend had told them that they had to kill someone to become a “witch.” Both of them were then indicted on the charges of first-degree murder and improper disposal of human skeletal remains. In March 2019, they were also charged with conspiracy to commit first-degree murder.
Bailey Boswell is Serving Her Sentence at a Nebraska Prison Today
Following Bailey and Aubrey’s arrest, the latter pleaded no contest to the charge of improper disposal of human skeletal remains. His separate jury trial began on June 18, 2019, during which the prosecution presented several digital pieces of evidence and CCTV footage before the court. They also pointed out that the defendant and Bailey remained in contact through coded letters while in custody. On the other hand, the defense insisted that she was only involved in the clear-up and didn’t take part in the murder. They acknowledged that Aubrey committed the homicide but claimed it was accidental. He was finally convicted of the murder and conspiracy charges.
Bailey’s jury trial began on September 23, 2020, during which the prosecution presented several witnesses, including Katie and Ashley. During their testimony, they stated that the defendant and Aubrey had recruited women into relationships and had discussed murder for sexual gratification. On the other hand, the defense challenged the admission of certain pieces of evidence related to sexual fantasies and testimony about witchcraft. Bailey was ultimately found guilty of all three charges on October 14, 2020. In June 2021, Aubrey received the death penalty and an additional 2-year term for improper disposal and a 50-year prison term for conspiracy.
On November 8, 2021, Bailey was sentenced to life imprisonment. Moreover, she received two consecutive sentences of 2 years for improper disposal and 50 years for the conspiracy charge. Following that, she appealed her convictions and sentences, arguing that the trial court erred in admitting evidence during the guilt phase of her trial. The Supreme Court rejected her claims and upheld the Trial Court’s judgment on May 10, 2024. As of writing, Bailey is incarcerated at the Nebraska Correctional Center for Women in York, Nebraska. Aubrey is currently on death row at the Tecumseh State Correctional Institution in Tecumseh, Nebraska.
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