It’s always nice when a date goes well, especially if the circumstances that led to the date were the result of a random hookup via online dating. It’s not easy to get back into the dating world these days, so a good blind date or Tinder date can be worth its weight in gold, confidence-wise.
The problem is, sometimes these “good dates” can be evidence of either innocuous politeness on the part of the blind date, if not something far more sinister. Our story begins with one of those dates and the culprits who would ultimately have you believe that their original purpose was anything but sinister…
It was November 14, 2017, and Nebraska-born Sydney Loofe was busy getting ready for her date. She had started using Tinder and had come across a man named Aubrey whom she wanted to get to know better. Little did she know that Aubrey’s plans for that same date were part of a much longer scheme.
Having Fun, Smoking Up
The two met up later that night. It was a Tuesday evening as both of them had been too busy over the weekend to get together. They hung out, smoked some marijuana, and even had Aubrey’s friend Bailey Boswell drive them around while they did so. It was a casual date and they got along really well…
One Devious Plot
Things went so well, in fact, that the two made plans to get together on Wednesday too. To anyone else, this would have seemed like the harmless beginning of a mutual attraction. To Aubrey Trail and Bailey Boswell, it was the beginning of a daring sexual encounter in the making. On their way to pick up Sydney, the two checked into a hotel near her home.
After they had stowed their belongings, the pair went on a 12-minute shopping trip at a nearby Home Depot. They picked up a laundry list of items including a hacksaw, tin snips, drop cloths, and utility knives. This was all added to the bleach, laundry detergent, duct tape, roasting pans, and trash bags that Boswell had purchased at the dollar store before leaving that day…
When Sydney didn’t show up for work the next day, folks began to get worried, It wasn’t like the 24-year-old to miss her shifts and she certainly wasn’t the type to not respond to texts. The eerie radio silence that surrounded Sydney Loofe soon gave way to worry that something had happened with her Tinder date.
Three Down Lines
If anyone has asked Aubrey Trail of Bailey Boswell about it, they would have said that they arrived on time to pick Sydney up. After that though, all three cell phones seemed to “go dark.” Of course, a police investigation soon revealed that Trail and Boswell’s phones weren’t dark at all, but moving from place to place throughout the night…
The police were eventually contacted and a county-wide search for Sydney soon began. Weeks passed and the cold December wind blew into Clay County. It was on such a day that a member of the search party discovered something amidst the barren fields of the countryside. A trash bag had been thrown into a ditch and an arm was sticking out the top of it.
More bags were soon discovered, each of them containing more body parts. At first, no one knew that it was Sydney, but a tattoo on one of the discovered upper arms revealed the truth. There, in inked letters was the phrase “Everything will be wonderful someday.” They had found Sydney Loofe. Well, most of her…
Tool marks on the remains seemed consistent with someone having used a hacksaw to dismember her. They also found marks on her back and the top of her head as well as ligature marks on her wrists. Whoever had done this to her, had held her captive in some way. The most disturbing revelation, however, was yet to come.
They may have found the majority of her body, but most of Sydney’s internal organs were still missing. Her heart, tongue, kidneys, and spleen were all missing. As far as her friends were concerned, there was only one person responsible; her Tinder date. They showed police the picture of Aubrey that she’d sent them before she first went out on the date…
Pretty soon, the police had Aubrey Trail in custody. It was only a short trip to connect him to Boswell. Meanwhile, though, Trail languished in police custody. He was skittish, nervous, and was soon spilling his guts to the detectives. He confessed that Sydney Loofe had died at his hand.”I killed Sydney Loofe,” he admitted. And that wasn’t all.
“I am accountable. I physically am the one who caused the end of her life. Me and only me,” he ended up telling the media afterward. He explained that he and Sydney were in a room with two other women, though he didn’t say who, and that he was holding an as yet unspecified object meant to restrict Sydney’s breathing. But why would he have that in the first place?
Leaving Things Out
The confession, notwithstanding, there were a number of problems with Trail’s story. First and foremost was the fact that he kept saying the killing was accidental. His receipts from Home Depot and his victim’s ligature marks made that all but impossible. Sydney had been brought there for a reason, and he knew what it was.
The detectives asked why he didn’t call 911 when this “strangling accident” first went wrong. Trail said he worried it wouldn’t be treated as an accident and again insisted that it was. He kept making excuses but also indicating that he deserved life in prison or even death. They wondered why he kept insisting on his own guilt when he clearly had accomplices…
A Fine Fibber
It was finally revealed, in a decoded jail note between Trail and Boswell, that Trail’s “accident” was no such thing. Trail had allegedly wanted to make a snuff film with Boswell and that he had lied to her, given her assurances that no one would get hurt, but that wasn’t true. He admitted he had planned to kill someone all along and that he used Boswell to help him.
The thing was, the note seemed forced as well. If Boswell thought it was all a game, why did she help him buy tools, bags, and cleaning materials? Why do all of that and then dispose of the hacksawed body? This unintentional murder was nothing of the sort. Trail had come up with the plan and Boswell must have been in on it. The problem was proving it…
Trail’s lawyers argued that Sydney had been offered money to participate in his sexual fantasy, one which involved erotic asphyxiation. According to him, Sydney’s death was neither intentional nor planned. It was hard to prove too, seeing as the body was cut into a dozen pieces. There was no way to prove asphyxiation at all.
Lies or the Truth?
It seems that prosecutors will have little choice but to charge but Trail and Boswell with Sydney’s death, even if there are other accomplices waiting in the wings. Trail has had numerous occasions to admit the total truth but seems content with offering himself up as the sole culprit in this case. Still, his subsequent trial was not without drama…
Trail didn’t say anything at all during the first week of his murder trial. On the first day of the second week, however, Trail shocked everyone standing up and shouting “Bailey is innocent, and I curse you all!” before slashing his neck three or four times. He had tried to cut his own throat. He survived with only minor injuries.
Despite his guilty plea and that dramatic display of failed suicide, Aubrey Trail will still face the death penalty for his crimes. The degree of evidence tampering, the apparent brutality of the murder, and the clear preparation all seem to point to a very dangerous man. It just goes to prove, be careful who you date when you get on Tinder.