Sydney Loofe /// Part 2 /// 865

Summary

True Crime Garage: Sydney Loofe /// Part 2 /// 865

Release Date: August 20, 2025
Hosts: Nic and the Captain

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Overview

In Part 2 of their deep dive into the tragic case of Sydney Loofe, hosts Nic and the Captain break down the backgrounds, criminal histories, arrest, and prosecution of Bailey Boswell and Aubrey Trail—two individuals responsible for Sydney’s murder. The episode details their histories, the investigation process, confessions, and evidence presented in their trials, as well as the resulting sentences. The hosts also discuss disturbing trial details, witness testimonies, and the impact of the case on the community and Loofe's family.

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Key Discussion Points & Insights

1. Background of the Suspects ([03:53]–[07:38])

• Bailey Boswell:

  • Her father was murdered when she was a baby, but she grew up in a loving family.
  • Was a promising athlete who later suffered a sexual assault in college and entered an abusive relationship with Freddie Pannell.
  • Developed a drug habit, lost custody of her daughter, and began advertising on Backpage for a sugar daddy, leading her to meet Aubrey Trail.
  • Engaged in theft and fraud with Trail, with losses estimated between $300,000-$500,000 across several states.

• Aubrey Trail:

  • Ex-convict from Tennessee, with a history of armed robbery and defrauding people.
  • Spent much of his life incarcerated or on parole.
  • Together with Boswell, operated various scams and became engaged in criminal activity, including passing bad checks and stealing rare coins.

Quote:
“These are two of the biggest piles of shit that have ever been on the show, and that's saying a lot.” — Captain ([08:38])

2. Arrest and Early Charges ([08:45]–[13:38])

• While in jail awaiting charges, Aubrey Trail tried to influence Boswell’s story via smuggled letters.
• Federal and state authorities charged them with stolen property offenses relating to transporting stolen goods over state lines.
• Both faced additional charges for theft and fraud schemes, receiving substantial prison sentences even before murder charges were brought.

Quote:
“He kept making statements like, ‘You want justice for Sydney, charge me.’” — Nic ([10:45])

3. Confessions and Legal Maneuvering ([10:45]–[15:42])

• Aubrey Trail gave three statements to the FBI and seemingly craved attention, admitting involvement in Loofe’s death but insisting Boswell was not present.
• In interviews, Trail shifted responsibility but eventually confessed:
  “I'm guilty. I did it. Let's get justice for Sydney Loofe. A life for a life. I should be put to death.” — Aubrey Trail (quoted by Nic, [11:56])
• Prosecutors spent months gathering evidence, preparing for a thorough case, as both suspects were already incarcerated.

4. Prosecution Strategy and Evidence ([15:42]–[21:12])

• Prosecutors intended to pursue the death penalty due to aggravating circumstances, including the depravity of the crime and Trail’s violent history.
• Surveillance footage from Home Depot showed the suspects buying tools used in Loofe’s murder and body disposal.
• Trail’s story changed frequently—alternating between accidental death and elaborate sex fantasy defense.
• The prosecution stressed premeditation, making the case that Loofe was targeted and murdered simply for the couple’s entertainment.

Quote:
“This was not a sexual fantasy gone wrong, but a premeditated murder gone right.” — Prosecutor (relayed by Nic, [22:51])

5. Behavior and Testimony During Trial ([21:12]–[36:13])

• Trail was disruptive and manipulative before and during trial, engaging in self-harm by slitting his throat in front of the jury (he survived; the judge ruled this a calculated gesture).
• Forensic anthropologist Dr. Stephen Symes testified to the brutal nature of Loofe’s death and dismemberment, highlighting use of multiple tools and the sadistic treatment of the body.
• Three women who previously spent time with Trail and Boswell testified to the pair’s preoccupation with torture and murder, as well as their coercive sexual dynamics.

Memorable Moment:
Aubrey Trail interrupts court proceedings by cutting his own throat, yelling, “Bailey is innocent and I curse you all.” ([26:11])
— The trial continued without him as he recovered in the hospital.

6. Witness Testimonies and Pattern of Behavior ([30:44]–[36:13])

• Victims testified that Trail and Boswell tried to recruit participants for murder and torture-themed videos, discussed witchcraft and vampirism, and imposed bizarre rules and humiliations on their “harem.”
• None of the women said choking was part of prior sexual activity, undermining the “fantasy gone wrong” defense.

Quote:
“Aubrey Trail was aroused by the idea of watching Bailey Boswell torture someone.” — Nic, summarizing witness testimony ([34:11])

7. Key Evidence and Contradictions ([37:45]–[43:09])

• Trail’s stories shifted, with repeated contradictions undercutting his credibility. He claimed Loofe’s death was accidental, then alluded to multiple women’s participation, then insisted only he was responsible.
• Cell phone data and digital communications were pivotal, tracing contacts and surveillance footage to the suspects’ clear premeditation.

Quote:
“This cell phone data will become just as important as DNA.” — Captain ([43:09])

8. Trial Outcomes and Sentencing ([43:55]–[49:15])

• Aubrey Trail: Found guilty of first-degree murder. The jury and a three-judge panel confirmed aggravating circumstances, sentencing him to death.
• Bailey Boswell: Convicted on all counts (first-degree murder, conspiracy to commit murder, improper disposal of human remains). Escaped the death penalty by a single judge’s vote; sentenced to life in prison plus additional years.

Quote:
“If this doesn't work warrant the death penalty, I feel Nebraska should just get rid of it.” — George Loofe, victim’s father ([50:12])

9. Aftermath and Reflections ([49:15]–[51:47])

• Both convictions and sentences were upheld on appeal.
• The hosts emphasize the senselessness of the killing and the choices that led Boswell and Trail to such depravity.
• Memorials for Sydney Loofe exist in her hometown and local zoo, reflecting her love of animals and her stolen potential.

Quote:
“She chose to kill, and therefore she chose her fate.” — Nic ([50:48])

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Notable Quotes & Memorable Moments

• “These are two of the biggest piles of shit that have ever been on the show, and that's saying a lot.” — Captain ([08:38])
• “I'm guilty. I did it. Let's get justice for Sydney Loofe. A life for a life. I should be put to death.” — Aubrey Trail, via prison phone ([11:56])
• “This was not a sexual fantasy gone wrong, but a premeditated murder gone right.” — Prosecutor ([22:51])
• Aubrey Trail’s courtroom outburst:
  Slashed his throat, yelling, “Bailey is innocent and I curse you all.” ([26:11])
• “This cell phone data will become just as important as DNA.” — Captain ([43:09])
• “If this doesn't work warrant the death penalty, I feel Nebraska should just get rid of it.” — George Loofe ([50:12])
• “She chose to kill, and therefore she chose her fate.” — Nic ([50:48])

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Important Timestamps

• Suspect backgrounds: [03:53]–[06:37]
• Description of criminal histories: [06:37]–[08:25]
• Early confessions and jail behavior: [08:45]–[13:38]
• Murder and conspiracy charges: [13:39]–[15:42]
• Trial strategy/prosecutors’ approach: [21:12]–[22:51]
• Trial disruptions (Trail’s self-harm): [26:11]
• Forensic and witness testimony: [29:10]–[36:13]
• Discussion of evidence/cell phone data: [43:09]
• Outcomes and sentencing recap: [43:55]–[49:15]
• Victim memorials and closing thoughts: [50:48]–[51:47]

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Tone and Style

• The hosts maintain their trademark irreverent, candid banter, blending dark humor (“bags of the year,” “wild things”) with empathy for victims and outrage at the cruelty of the perpetrators.
• Emotional responses—anger, disbelief, empathy—punctuate the in-depth, methodical recounting of criminal investigations and trial proceedings.
• There’s a recurring thread: a respect for meticulous police work and for preserving the dignity and memory of Sydney Loofe.

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Summary for New Listeners

This episode offers a comprehensive breakdown of how a young woman full of promise fell prey to two manipulative, sadistic predators—and how law enforcement, through persistent detective work and mounting digital evidence, ultimately secured convictions and sentences that reflected the extremity of the crime. The testimony at trial, the strategies employed, and the psychological games played by the perpetrators provide a disturbing glimpse into criminal pathology, while the hosts’ commentary anchors the case in moral clarity and respect for the victim. If you want to understand both the details of the Loofe case and its broader implications for justice and true crime investigation, this episode covers all the major ground.

Transcript

[A]

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[A]

Foreign welcome to True Crime Garage wherever you are, whatever you're doing. Thanks for listening. I'm your host Nick and with me as always, is a man who is dressed up like a heart attack for you. Here is the Captain.

[B]

It's good to be seen and good to see you. Thanks for listening. Thanks for telling a friend.

[A]

We are still moving our way through some delicious. It's like a dessert in a pint glass. This is moonlit Imperial Stout. This is chocolate and coffee and not too boozy. Actually not boozy at all because of the heat. Though I did chill this one overnight in the fridge. Garage grade 4 out of 5 bottle caps. And here are some folks that just might be drinking at home in their garage as I speak. First up we have Robert Maxwell in beautiful Louisville, Kentucky.

[B]

And a big wheelike jib goes out to Jenny from Little Rock, Arkansas.

[A]

Next, here's a cheers to May and the heart of it all, Columbus, Ohio.

[B]

Tall cans in the air To Melissa from Philadelphia. Fly Eagles, fly.

[A]

And last but certainly not least, we have Christina from parts unknown. Everyone we just mentioned went to truecrimegarage.com clicked on the pint glass and helped us out with this week's beer fund for the beer run filling up the old garage fridge. And for that we thank you.

[B]

Yeah, BW Double arguing beer on. Hey, want to help out the show Wherever you listen, Leave a five star review and we'll love you for the rest of our lives. And that's enough of the business.

[A]

All right everybody gather round. Grab a chair, grab a beer. Let's talk some true crime.

[B]

Sam.

[A]

So I want to get into these suspects here a bit. Captain and I guess technically at this time in our timeline that they are persons of interest, but they, I mean, if law enforcement were vultures, they would be circling around these two endlessly because there's so much telling them that these folks are absolutely responsible for the disappearance. Now let's figure out their level involvement and what exactly happened here. We did some background on these two and here's what we found. Bailey's biological father was murdered when she was a baby. But despite this, she had a very normal upbringing by all accounts with her with a mom, stepdad and grandparents who were loving and supportive. She was an excellent track and basketball athlete in high school, this in Leon, Iowa. And she was awarded a basketball scholarship to play in Des Moines. But it's, it's unclear if she accepted this scholarship. Her family said that Bailey was a normal kid who did not get into trouble, but she was sexually assaulted in college and she got into a very physically abusive relationship. This was with a one Freddie Pannell. Pannell P A N N E L L. That turned, and they say, her folks say turned her down a very dark path. The Boswells claim that Bailey had tried to escape Freddie, even filing a restraining order against him. But prosecutors said that Bailey and Freddie were druggies. Bailey lost custody of her daughter because of her habit. She was arrested in 2016, just one year before Sidney went missing and was killed this for possession of drug paraphernalia in Cameron, Missouri. At some point, she started advertising on Backpage looking for a sugar daddy, which is how she met Aubrey. The two seemed to form an unlikely pair and teamed up to steal, swindle and defraud people at antique booths, at traveling shows as well as their online antique store. They were together for more than a year, during which they racked up some serious charges. They were passing bad checks, including making off with $28,000 worth of rare coins. Aubrey and Bailey were believed to have been involved in between $300,000 to $500,000 in theft and bad check cases. And this spans several states.

[B]

Cocaine is a hell of a drug.

[A]

From the Grand Island Independent quote. Boswell joined up with Trail, an ex convict from Tennessee, for a life of stealing and selling antiques, visiting casinos and engaging young women for parties and group sex. End quote. Aubrey was twice Bailey's age, probably three times her weight, and they made for one very strange and very evil couple. Aubrey Trail spent his teenage years in troubled environments, including a juvenile detention facility. He was incarcerated for the first time at age 17 for armed robbery and has spent most of his life incarcerated or on parole, he had done two prison stints for defrauding people out of valuable antiques. Normally, this would cue the captain to say that he's a piece of. But we covered that extensively in part one of this story.

[B]

I can say it again if you want. This guy's a giant piece of. But also, like, and I'm not trying to feel bad for any of these losers, but when you hear a story of a individual that had scholarship offers to go play a sport at a collegiate level and then their life turns into this, you just think, man, that. That sucks. It sucks for her family, it sucks for her friends, sucks for her. It sucks for everybody that basically was in the path of this destruction. I think all of this comes down, when it comes down to. To Bailey, is she was a drug addict and was willing to almost do anything to make sure that she could get drugs.

[A]

Well, you know, one could say her life turned into this. Another could say she turned her life right into this and that. From. From where I stand, that's kind of how I see it now.

[B]

I mean, these are two of the biggest piles of shit that have ever been on the show, and that's saying a lot.

[A]

So they're. They're locked up, right? They're in jail awaiting charges. Aubrey is caught trying to slip Bailey notes when they're in jail. And one he wrote, quote, here is your story, end quote, and told her to tell the investigators that they were paid lots of money by young women to act out killing, torture, and sex fantasies. So essentially, what. What this story would be is that women would pay this couple to act out these different fantasies with that woman. And in some cases, it included photographing, videotaping, or recording. Videotaping, I shouldn't say that recording these acts. Now, here come the charges, though. This is both federal and state authorities. This is December of 2017. They charged them with carrying stolen merchandise valued at more than $5,000 across state lines. And Aubrey was handed over to the U.S. marshals on a federal theft charge that he and Bailey had defrauded a Kansas couple out of $375,000, approximately, in an overseas gold coin scheme and transported the property over state lines. But charges on the Sydney Loof case were a long time coming. The. The other criminal cases proceeded, and they both were facing years in prison on those cases. You know, this is a guy. If you follow this story long enough, it seems like this guy enjoyed the spotlight, right? The accused killer, or would be accused killer sitting in the county jail. Aubrey trail, on three separate occasions, spoke with Reporters from the Omaha World Herald. He said he had given three separate statements on the Loof case to the FBI. He admitted he expected to be charged. In fact, he asked for charges. He kept making statements like, quote, you want justice for Sydney, Charge me. End quote. He was challenging the authorities and almost seemed like he wanted to be charged, saying, the FBI has pulled so many hairs out of my head, I've got a bald spot. In a second recorded jailhouse phone call, Aubrey told the Omaha World Herald that I told law enforcement, enforcement a long time ago that I am accountable for Sidney Lu's death. I am responsible. The girl, presumably meaning Bailey, had nothing to do with it. And then a flat out confession. Aubrey told reporter Paul Hamel that he accidentally suffocated Sydney to death in the basement apartment he and Bailey rented. In Wilbur Hamel's reporting states, trail claimed that Loof was a willing participant in a sexual fantasy with himself and at least two other women, but that Bailey Boswell was wiped out on drugs and outside the room when Lou died, Aubrey seemed to want to pay for his crime. In February 2018, he told the reporter in another prison phone call that he was ready to be charged. Quote, I'm guilty. I did it. Let's get justice for Sydney Loof. A life for a life. I should be put to death, end quote.

[B]

Yeah, but even if you buy his story.

[A]

Stories.

[B]

His stories. Yeah, stories. Then Bailey is still responsible on some level. She is a. She's involved somehow.

[A]

Well, several months would go by while prosecutors gathered evidence amassing like 500 potential witnesses and figured out. They had to figure out where the prosecution should be handled too, because we have this detail of Sidney living in one county in Lancaster county, and it's believed she was killed in Saline county, was disposed of in Clay County. Now, like you said prior, both of these suspects are already in jail facing other charges, so there's no real rush to try them. It's more. Let's. We have the time, so let's get this absolutely right. Let's. Let's get this perfect. In January of 2018, Aubrey entered not guilty pleas to 13 federal indictments related to stolen property. Then later, they both end up pleading guilty. Two charges, very similar charges. So what happens here, Captain? In two separate sentencing hearings, Bailey Boswell gets five years in prison and Aubrey Trail got 10 years. This for defrauding that Kansas couple out of nearly $400,000.

[B]

Wow.

[A]

Then from Saline county, in June of 2018, this is when both Bailey and Aubrey were charged with first degree murder and abandoning a remains from Omaha.com's state prosecutors alleged that Loof's death was deliberate and premeditated. Among their evidence is surveillance camera footage from a Lincoln Home Depot store of trail and Boswell buying tools and supplies believed to have been used in the dismemberment and disposal of loose body. According to court records, Sydney was strangled with an extension cord, the court documents alleged, by either Bailey or Aubrey. Either way, the prosecutors intended to pursue the death penalty for Aubrey. Court papers filed by the Nebraska Attorney General's office alleged that two aggravating circumstances warranted the capital punishment. This was that Aubrey had a substantial history of serious assaultative and terrorizing criminal activity and that Sidney's murder was done with exceptional depravity. Another charge was soon slapped on Aubrey. This is conspiracy to commit murder. The charge alleged that he had conspired with Bailey between July and October of 2017 to solicit young women online, recruit participants in a homicide, and select a victim to murder. The two were casting a wide net.

[B]

Right.

[A]

And Sidney fell into a trap. Aubrey pled guilty to additional charges, this of improper disposal of human remains. But on the serious charges, like the first degree murder, he pled not guilty. But we have a trial to discuss here, Captain.

[B]

Yeah. So he pled not guilty, but he confessed to it.

[A]

No. So he. He pled guilty to the charge of improper disposal of human remains.

[B]

Right.

[A]

But he. He pleads not guilty to the more serious charges, the main one being that first degree. Right. But this dude and I. You hear me laughing, not because I find it to be humorous, but because I. I find it to be exhaustingly aggravating. This dude was a serious pain in the ass during the pretrial period.

[B]

He's a loser.

[A]

So, of course, his attorney filed all sorts of motions claiming his statements to police were coerced and claiming that he had an alibi. That's all normal stuff. No one cared. And those motions were all rejected.

[B]

Good.

[A]

Aubrey made claims that Sidney, the victim, was involved in the coin fraud scheme, that they had known her much longer than this short period on Tinder.

[B]

Right.

[A]

Then he claims other inmates were threatening him. So he gets placed in solitary for his own safety. To which then as soon as he's there, he promptly asks for tv. Like, oh, can you give me a tv? The answer's no, dude. The answer is no. No TV for you. He requested special housing, saying that he had health issues. And then after a psych evaluation, Aubrey was found fit to stand trial. Then at the trial the state had lined up. Remember we mentioned potentially 500 witnesses that they were going to call during the course of this trial. This included clerks at antique stores, clerks at motels and casinos where the pair allegedly spent a lot of money, two ex wives of trail, and dozens of law enforcement members who aided in the investigation and the search for both Sydney and for those perps. The prosecutor made sure the jury knew that Aubrey and Bailey Boswell recruited Sidney with the sole intention of murdering her simply for their entertainment and pleasure.

[B]

Yeah, they're evil animals. Do you think there's something about, like, prison justice? Because I've been thinking a lot about this. There's all these reports now with, you know, Brian Coburger where he gets in prison and. And these people are harassing him and, and taunting him through the vents. And obviously they have to take all this into account because these animals want to get to him. But do you think these. The people he's in prison with are bad people? Are they doing this to make, you know, two wrongs make a right? Or is it. I think some of it has to do with. If there's too much attention on a case, the people in prison, some somehow want to make a statement. And I think you see the same thing here. It's like. It seems like Aubrey was braggadocious and, and wanted to be in the spotlight and wanted to take credit for this crime and one of these horrible details out there. But then once he gets behind bars, it seems like, you know, the animals wanted to get him.

[A]

Who knows? Who knows? I mean, there's cases where people are placed in solitary for their own safety when it's absolutely necessary. And then there's other. Keep in mind, you know, my statement here was that he claimed other inmates were threatening him. We do know of other cases where an individual goes to jail and then fabricates threats that does get them placed into solitary. So.

[B]

Right.

[A]

You know, typically a person that has this length of rap sheet is a. A bully for. Not so much in the traditional sense, but a bully in the way of how they move and live in society. If they want something, they take it, or they steal it from you or they defraud you out of your money. And he did all this. And it's manipulative and it's trying to control every scenario and benefit. Find a way to benefit in any scenario that you're placed into, whether you actually deserve to benefit or have done any real work to achieve a higher status or a better position in your situation. So it's. I mean, as far as this goes, I don't put a whole Lot of thought into this. I, you know, I, that my, my drive for true crime is always the investigations and how, how do we find, how do we figure out who's responsible for this and then how do we apprehend them? That to me is the stuff that, that I find intriguing. That's the stuff that I've, that's what the smart good people are doing, strategizing and learning and educating themselves on to do Once, once a Aubry gets put into jail with, with a whole bunch of other guilty people.

[B]

The wild things.

[A]

It could be Lord of the Flies for all I care. I don't, I don't. That's, you know, they're not part of my society. They're not. I actually pay taxes to make sure that they are not. So however they sort it out in there, that's, that's up to them.

[B]

Is it bad that there's a part of me that likes the monsters threatening and scaring this. The, the boogeyman? Cuz in all these cases that person, you know, Brian Coburger becomes the boogeyman. But not once he's behind bars.

[A]

No. It's human nature. It would be weird if you didn't. Because it, it's because I like it.

[B]

I probably like it more than I should.

[A]

When people do stuff as heinous and hurtful and heartless and soulless as the crimes that we are regularly discussing on this show. It is not, it doesn't ever sit well to just go, oh well, they did all this horrible and now they're, they're essentially getting a 25 year long timeout. It's just not, there's no, there's nothing that, that feels good about, about that punishment. The, one of the things that the. And this was a good strategic move by the prosecutor. I, I like to. Because they spend so much time focusing on how they present things and the words that they choose to use in the delivery of those words to the jury. And one thing he told the jury was that they go into detail about when Bailey picked Sidney up using the ruse about a date with Bailey, pointing out that these two were already prepared with everything that they needed to kill, dismember and dispose. And he goes on to tell the jury that the two were hoping and planning to murder someone, anyone. For months. He told the jury, quote, this was not a sexual fantasy gone wrong, but a premeditated murder gone right. The other prosecutor here was from the Nebraska Attorney General's office who took up from there. She said this is more than first degree murder. This was a planned abduction to kill Sidney Loofah then describing in painstaking detail how Sidney was dismembered. At this point, Sidney's sister and father left the courtroom. The prosecutor, she threw in the Sidney's internal organs. Some of them were never found. And in Aubrey's interview he had only said vaguely that they had drained her blood because he was very thirsty that day. Now this was a tactic. This tactic by the prosecutors was deliberate because remember Aubrey pled guilty pre trial to the improper disposal of human remains. That was a tactic that was designed to avoid showing the horrific images of the dismembered body to the jury. So the thought was if, if he's already guilty of improper disposal of human remains, that that can't work its way into this trial, right? By talking about the autopsy and Aubrey's air quotes confession, the prosecution managed to get them in the trial deliberately to horrify the jury. Astonishingly, Aubrey managed to slip a razor blade into court and tried to take his own life right there in front of the jury. He slashed his throat and yelled, bailey is innocent and I curse you all. Now he lived. But blood had to be cleaned up off of the courtroom floor and the judge refused to declare a mistrial, ruling that Aubrey's act of self harm was, quote, a calculated gesture resulting in superficial cuts. The trial continued in Aubrey's absence as he recovered in the hospital. Summer's winding down and whether your kids are just soaking up the last few weeks or already asking when school starts, this is the perfect time to ease back into learning with ixl. 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[B]

All right, we are back. Make sure you check out off the record only. Only if you're nasty. Cheers to you and talk canes in the air to you, my friend.

[A]

Well, you could check it out if you are not currently nasty, but desire to be nasty because you will become nasty in the most beautiful of ways. That's so for new listeners, off the Record is our subscription show available on Patreon and Apple. Subscription. And you'll get dozens and dozens of shows of, of off the record. We've been recording them for a long time and we even, you even get our first 50 episodes and some other bonus episodes that we've done throughout the year. So.

[B]

And they're not that good.

[A]

A lot of stuff. Way to sell it to the people.

[B]

Well, you, you can see how the show started and how it has grown. But let's get, let's get back to these bags of the year.

[A]

Yeah, so we have a forensic anthropolog, MS, Stephen Symes, who is going to be testifying on behalf of the prosecution to discuss at length the brutal death and the suffering of the victim as well as the barbaric treatment of the body and telling jurors that a saw, a knife and scissor like tools were used to dismember the body. Remember tin snips and some other items. We talked about the grocery list of items that were purchased at the hardware store. This from Omaha.com's Siemes who said he specializes in cases of body dismemberment, examined loose remains on December 13, 2017. He used a model of a skeleton at times to show jurors how loose body was cut up. He said it appeared from the characteristics of the cuts that a knife was used to remove flesh and then a saw was used to cut through the bones with several false start cuts. A scissors like tool like tin snips was used on the rib area, he said. And then there were the witnesses to the premeditated nature of the crime. This was, this is something you don't often see in murder case trials at all. So we get three female witnesses who had lived or spent time with this terrible couple before Sidney's murder.

[B]

Right?

[A]

So these three different ladies, they testified that the pair often talked about torturing and killing someone. Their reasons to kill, Witchcraft. Aubrey claimed he could fly and that he was a vampire and that he had a harem of witches. Not the good kind. Glinda. These women all told the jury that they, just like Sidney, met Bailey on Tinder. Once they met in person, she introduces them to her sugar daddy, Aubrey. They coerced them into group sex and bondage activities in exchange for financial assistance like a weekly allowance. Now, I think a key here is that none of these three women, it should be noted none of them ever testified that they had experienced choking as part of any of these sexual activities.

[B]

Can you imagine though, you go on back page looking for sugar daddy and you end up in a basement. That's what the sugar daddy provides. But I'm guessing all these women, all these, I guess, quote unquote eyewitnesses, they're all drug users, heavy drug users.

[A]

I, I don't know about that. That wasn't part of their testimony. And keep in mind, they weren't looking, they weren't looking for a sugar daddy. They were looking for a female.

[B]

Right?

[A]

And they, they found, they found Bailey, who then introduces them to Aubrey.

[B]

It's a bizarre story.

[A]

They will fall out of touch with most of them when the arrangement. Because these arrangements, what happens is they start off soft and then they get worse and worse. They get a little more violent, right? More depraved. Bailey's essentially looking for a submissive and so submit people who want to be a submissive show up, they meet Bailey and now they're submit, submitting to Her. But now there's this other. There's this other person involved. Went from weird to crazy strange.

[B]

Weird might be fun for some people, but I think once that couple starts talking about that he can fly and that they want to murder somebody, you stop returning their texts and their calls.

[A]

Well, and mind you, this guy who claims he can fly is sitting in a wheelchair during the course of this trial. So, yeah, appears he lost that ability.

[B]

That's because he. He flew too high and. And fell.

[A]

Yeah. Well, and.

[B]

But the purpose of calling eggs on the landing.

[A]

The purpose of calling these witnesses was to point out that it's like one of the. Well, yeah, but like, one of the prosecutors were saying it wasn't the. The Tinder communication with Sidney Loof was completely targeting her and trying to. To set up a scenario where they could abduct, attack, and murder this woman before she became a victim. They were looking for a nameless victim. These women are testifying that these two were aroused by the idea of watching. So one of the statements was something to this effect here. Captain Aubrey Trejl was aroused by the idea of watching Bailey Boswell torture someone. Let's get into some of the details without. I don't want to go through all of it because it was very lengthy, but among some of the details of these witnesses in their test, in their testimony at trial, Aubrey and Bailey wanted one of the women to select someone to kill and torture so they could videotape the act and sell it, saying that they could make a million dollars to sell the snuff film. They stated that Bailey wanted one of the women to torture and kill someone to prove her loyalty to Bailey in their dominant submissive sexual relationship. The woman said the order was later dropped after she proved her worth, that each of the women were mostly met up with. The pair, who mostly met up with the pair individually, was paid between $150 to $200 a week as some sort of allowance. But they said the payments came with a set of rules, including that Aubrey be called daddy and Bailey mommy and remaining naked while they're in the apartment at all times. Also participating in group sex sessions and submitting to punishment, including whippings. I forgot, too. One of his other supernatural powers was he had the ability to put Bailey in a trance.

[B]

Sure.

[A]

One of the women testified that she had a fantasy of being a cat, complete with a leash and collar. But she said that she was humiliated when she was ordered to eat cat food out of a bowl.

[B]

But she wanted. She wanted to be a cat.

[A]

Hey, you want to you want to.

[B]

Be cats, you got to eat the cat food.

[A]

You got to walk the walk.

[B]

What's wrong with people?

[A]

We don't have enough time. They also testified that Bailey enjoyed pain during sex and wanted one of the young women to talk about acts of torture while engaging in sex with her. Bailey, the woman testified, also talked of dismembering a body and breaking someone's fingers as a form of torture.

[B]

Jesus Christ.

[A]

And that Aubrey had what he called a kill bag that contained a hammer, pliers, and a sauna suit. Remember, there was a sauna suit found with the trash bags and body parts. One of the women who was with the couple on the failed cocaine drop in grand island, or we probably more. It's more accurate to say the fake cocaine drop when they were on the run. Testified.

[B]

Drop cocaine from the skies.

[A]

Testified that Bailey and Aubrey talked about being on the lookout for a victim to torture and kill, Quote, someone who would not be missed. The plan was for Aubrey to watch Bailey and the woman commit murder. This. I don't know if I mentioned it already, Captain, but it sounds like they even may have had their eyes on a. A student or a foreign student. Think about this for a second here. Look, these two are not overly smart, but we do know that they're planning.

[B]

You don't need to be smart if you can fly.

[A]

They're planning all of this. If the family doesn't sound the alarm right away, if the friend doesn't turn into Adrian Monk and sort the whole thing out and figure out what's going on and supply the absolute best lead possible to police. If all these dominoes don't fall in this order, how soon would they have moved on to victim number two?

[B]

And because the distance they lived away from Sidney, would they become suspects at all? Because since they were using fake names and they were basically catfishing on Tinder. Just think if Sydney was in a place where she didn't tell anybody about a date, we would have no leads. And even the Snapchat picture, you could go, well, she said she's going on a date, but we don't know how she's getting dates. We don't know if she met somebody. And then again, they would go to her inner circle and the people at her work, and they would have nowhere to go as far as information. She just. Poof. Gone.

[A]

Well, and a lot of this, too. You know, I. Every bit of this, you could say, whoa, this powerful piece of evidence. This powerful. I mean, there's so many incredibly powerful and significant pieces of evidence. In this trial that were presented at the trial. But we can't overlook that they had video of the three hour FBI interrogation of Aubrey. This is shown. The entire session was shown to the jury. And remember when he is. It seems like at this point his concern is not for himself. It's more of, well, Bailey's not guilty. Wasn't there when, when, when Sidney died. His story is. Is changing on the details of a lot of this relationship. Right. At times saying that they had known Sidney for a long time. I point, he says they had known her for a year prior to the murder.

[B]

Yeah, but that doesn't line up with the surveillance footage at Menards. Right.

[A]

Well, and it doesn't line. The other thing too is it doesn't line up with other stories he's. He's telling as well. So it's. I mean, which, which one would you like for me to believe, sir? You know, which. Which of your stories most benefits you? What suits you today?

[B]

I hope somebody rips his face off in jail.

[A]

Regarding the. The missing organs. This part is weird because he, He. He's simply saying that they drained her blood. Remember he said something like he. Because he was thirsty that day. Yeah. But then he says that they deposited her blood and soul at a secret location. And that's about as much of that as we get. But he does say this too. In one of the portions of being interrogated, he says, quote, I'm a low down piece of a. Or whatever, but I'm not giving anyone up.

[B]

Meaning that there's more people involved.

[A]

Look, Bailey's absolutely involved. I think he's just trying to protect her.

[B]

Right.

[A]

In some form or fashion. But.

[B]

So, but look, there could be somebody else that was there. They. We know that they were doing stuff with other people. It's very possible that somebody else was there that didn't know what was going to go down.

[A]

Yeah, well, he says two other people, two other women were there. Yeah, but Bailey was outside knocked out on drugs. But then he goes into this dissertation of his weird ass belief system where he was saying, look, when we disposed of the body, everyone who was there when Luff died had to leave something they liked or something personal to them at the disposal site. And he said that this is some form of apology that they could give. But he also goes on several times to maintain that he alone was responsible for Sidney's death. Sidney Luff's death, and that Bailey Boswell was not present when Sidney died. And he claimed that Bailey Boswell was later forced to help cut up and Dispose of the body. And look, his story's all over the place. First she accidentally died during rough sex. Then he's claiming multiple people were involved. But not Bailey. She's innocent. Oh, but wait. She had helped, but only because he forced her to. He refused to name the other participants because they do not. Well, they don't exist. At trial, Aubrey's story changed again. His court appointed attorney, Joe Murray asked jurors to keep an open mind. Even though Aubrey Trail is not a particularly nice man, he says, but the truth is that Sydney Loop's death was a completely, was completely accidental and not a premeditated scheme to kill a young woman. And just like you said, Captain, you're ahead of it here because that doesn't go along with all of their actions and confirmed movements. Some of them, I mean, these are the, the trail, it's digital. It's on the phones, it's on communications between the killers, between the victim and one of the killers and their actions and activities at these do it yourself stores.

[B]

Well, but you've been saying it for a long time and, and I think it's one of the smartest things you've actually said that this cell phone data will become just as important as DNA.

[A]

And a lot of these more. I think it's already more important if the agencies that seem to know, the departments that seem to know how to use it and to use it immediately are, are clearing cases and making arrest very quickly. And those are stories that don't necessarily make it all the way to nationwide because it's, we're looking for the killer, boom, we found them. And, and so the story doesn't have any legs because it's very quick that they find the person responsible and get them off of the streets. And it's all because of you got this phone on you. And yeah, I don't, we don't need to go into too much detail about that.

[B]

So what happens to these asshats?

[A]

What I could take away from his trial, the trail trial, if you want to call it that, was that they were trying to push forward the idea that this was simply sex game gone wrong and that, yeah, they went way over the top to try to cover it up. It's weird because Aubrey did testify. He says that he doesn't contest a lot of what the prosecution's case is, but he's saying, you know, he had that explanation for what actually happened. Sex game gone wrong. But then in this version of it, it's she was accidentally strangled from behind during three way rough sex between him and Bailey and Sidney. So I mean it goes, it goes on and on and on. But again, it doesn't explain why you are purchasing things for a murder kit and to cover it up before the date, before Bailey and Sidney's date on the 15th. You're buying this stuff, right? So you can't say, well this, this was disposing of her body in this horrific barbaric manner that we chose to do was reactionary to an accident. We don't plan an accident, you plan to cover something up. And everything that the state was showing proved in my opinion, that, and the jury believed it as well. You know, he was found guilty. The same jury was reconvened to consider whether Aubrey should be given the death penalty. This is, was like a short mini trial, if you will. They had to believe that the, there were aggravating circumstances involved here in which, I mean we've gone through a lot of the details here. It was, you got to prove that it's premeditated and you got to prove that, prove beyond a reasonable doubt that the murder manifested exceptional depravity by ordinary standards of morality and intelligence. That's, that's the court jargon here for the legal words here for this in their state and of course they unanimously voted for death. So in Nebraska, from my understanding here, captain, you have the jury, they have to push for death, but then you have a three judge system. So if the jury finds that the crime met the criteria, then three judges would consider any mitigating circumstances and determine the actual final sentencing. So this is about as thorough as it gets as far as I'm concerned. And so he faced the same jury twice, once to find if he's guilty, two to figure out if the circumstances met the criteria for the death penalty, and then three, a three judge panel to confirm if that was going to be the punishment or not. And that's what he gets. Now Bailey, unlike Aubrey, was completely different during her trial. She was silent during the pre trial period and silent and on her best behavior during the trial. But all of the same evidence that we covered in the trail trial is all that was presented at Bailey's trial as well. And the results here are same, but different. The jury took just three and a half hours to convict Bailey on all three charges. First degree murder, conspiracy to commit murder, and improper disposal of human remains. In the sentencing phase, going for the death penalty, the prosecutor showed the jury the severed arm, superficial cuts. They, they showed everything they could to point out that not just was this premeditated, it was exceptionally depraved, one of the worst. And that she was. I mean, here's the part of it. Like you can have people that go on the stand and testify that because of violence that Bailey experienced in her life and trauma that she experienced in her life, that those are some form of mitigating factors that you need to consider. But you also need to consider this. She did a lot of the legwork to make sure that this woman was abducted and murdered. Had she not done a lot of that legwork, then this may have never happened. So she is found guilty, she doesn't get the death penalty. Because in this situation, the judges, the three judges, it's not majority rules. It's got to be unanimous. So two of the judges believed that the death penalty was appropriate and one did not. She doesn't get the death penalty, she gets life in prison. Plus she gets like a 50 years for conspiracy charge and two years for unlawful, unlawful disposal of human remains afterwards. We have. Sydney's parents, George and Susie Luff, said they were thankful that Bailey and Aubrey will never see the light of day. George Loof added, however, that if this doesn't work warrant the death penalty, I feel Nebraska should just get rid of it. I believe that Bailey Boswell is as guilty or guiltier. If it wasn't for her, my daughter would never have been there. He said. There were appeals by both individuals, but Nebraska supreme court affirmed the convictions, the death sentence and the life sentence as well. Sidney Loof was an animal lover. She aspired to work with creatures big and small. Memorial benches for Sidney can be found at her hometown city park and at the zoo and aquarium in Omaha. Her headstone is shaped like an angel. This is just another senseless killing. We suspect that Bailey and Aubrey, now facing the remainder of their sorry lives in prison cells, could not even articulate a reason why Bailey was full of self serving tears when it came to begging for her life. But where was that sympathy when it came to Sidney? As Bailey's family said about her, she was a normal kid. She had a loving upbringing. She was not raised to be a monster. She chose to help Aubrey find victims for their depraved fantasies involving sexual sadism. She chose to make others submit to her using coercion and violence. She chose to subject others to fear, pain and debasement. She chose to kill, and therefore she chose her fate. As for Aubrey, he fostered a cult of personality with himself at the center and used fear, pain and torture to subjugate women to his increasingly sadistic demands, which eventually culminated in murder. We will be watching to see whether Aubrey's death sentence is ever carried out. I cannot think of a much more deserving canon.

[B]

Want to thank everybody for joining us here in the garage. Thanks for telling your mother. Thanks for telling your brother. Make sure you subscribe to the podcast. And colonel, do we have any recommended reading for the beautiful listeners?

[A]

Yeah, one of our good friends hey is put out their first I say first because I believe there's going to be a number two or number three to come.

[B]

Some say this will be her first number two.

[A]

There you go. Lauren Samples True crime book recently released titled through the Shadows, Unsolved Crimes and the Search for Truth. Many of you will know her from the Paradise After Dark podcast and people that have gone to CrimeCon have have seen them on Creators Row Podcast Row. And it's complete with some essays by one by yours truly, also one by Sharon Newman Edwards, Robin Warder and Kelly Brink. So check that out. The reviews are really good on Amazon right now. The title is through the Shadows, Unsolved Crimes in the Search for Truth by Lauren Samples. You can find that title and many other great recommendations on our recommended page atTrue Crime Garage.com and until next week.

[B]

Be good, be kind, and don't litter. Sam.