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Sydney Loofe /// Part 1 /// 864 - True Crime Garage | Wave AI Podcast Notes

Sydney Loofe /// Part 1 /// 864

Tue Aug 19 2025

This week we take a look at a very strange case out of Lincoln, Nebraska. This is a case that caught everyone’s attention late in 2017. 24 Year old Sydney Loofe failed to show up for work. Friends and family could not get in contact with the usually very reliable young woman. After alerting police and reporting her missing, it was discovered that her last known communication was that she was ready for her date. Sydney was going out on date number two with a woman that she met on the Tinder app.

Summary

True Crime Garage – Sydney Loofe /// Part 1 /// 864

Podcast & Hosts: True Crime Garage, hosted by Nic and the Captain
Date: August 19, 2025
Episode Focus: The disappearance and murder of Sydney Loofe in Nebraska in 2017, focusing on the initial investigation and the key figures involved.

Episode Overview

In this gripping first installment, Nic and the Captain delve into the mysterious disappearance of 24-year-old Sydney Loofe from Lincoln, Nebraska. The episode unpacks her background, the disturbing details of her vanishing, the rapid escalation of the search, and the emerging suspects. With their trademark banter, the hosts guide listeners through the dark twists of the case, highlighting the unsettling power of online relationships and the dangers lurking behind social media profiles.

Key Discussion Points & Insights

1. Sydney Loofe’s Life and Circumstances Before Disappearance

Background:
- Born 1993, Broken Bow, Nebraska; parents were prominent educators in the community.
- Close-knit family, active in school and community; involved in sports and clubs until a scoliosis diagnosis (03:20).
- Had mental health struggles – anxiety and depression, managed since high school, worsening by 2017 (04:30).
- Recent job dissatisfaction and struggles; working at Menards but seeking a veterinary job (04:50).
- Known by friends as kind, polite, and someone who helped out others.
Notable Quote:
- Nick (04:25): "She was the kind of person who took people in when they were struggling to pay their rent or between places to live... but that dream sadly would not come to fruition."
Concerns:
- Recently began a new antidepressant prescription; family worried about side effects (06:55).
- Last seen by her mother at a doctor’s appointment in Lincoln before the disappearance.

2. Timeline and Discovery of Disappearance

November 15, 2017:
- Sydney excited about a second date; sends "ready for my date?" Snapchat to her friend Tara (02:32).
- Does not return home; doesn’t show up for work November 16th; phone goes straight to voicemail.
- Apartment found with her car outside, purse and glasses inside, hungry cat, and lights left on (08:29).
- Uncharacteristic absence raises immediate concern—parents report her missing by 5pm on the 16th.
Escalation:
- Police and family rapidly mobilize, suspicious due to Sydney's responsible habits.
- Sydney’s phone last pings in Wilbur, Nebraska, ~40 miles from her apartment (10:46).
Quote Highlight:
- Captain (08:10): "Some of these antidepressants can make people suicidal, even if they weren't suicidal before."
- Nick (11:16): "It was evident that Sidney, or at least her phone, got to this location 40 miles away via someone else."

3. Immediate Investigation and Public Attention

Community & Media Response:
- Vigils, green ribbons, social media campaigns (16:24).
- Description and tattoo photos distributed.
- Family’s public appeals (15:19): “We feel that she could be anywhere… Please continue to share these posts and pray for her safe return.”
Law Enforcement:
- Lincoln PD, Saline County Sheriff, Nebraska State Patrol, US Marshals, FBI all involved (18:16).
- Billboard near Interstate 80, NAMUS page, and two Facebook pages set up for tips and coverage.

4. The ‘Audrey’ Tinder Lead and Breakthrough

Digital Breadcrumbs:
- Friends confirm Sydney had shared she was on Tinder; was open about online dating (15:08).
- Tara shares "ready for my date" Snapchat and confirms date was with a woman named 'Audrey' (13:57).
- Friend Brooklyn undertakes her own ‘catfish’ operation to match with Audrey on Tinder, secures phone number and information, feeds to authorities (19:45-20:09).
Quote Highlight:
- Captain (19:45): “This is very smart.”
- Nick (21:24): “Bingo, bango, Jingo, Django. Audrey lived [in Wilbur] and she lived there with her boyfriend.”

5. Aubrey Trail and Bailey Boswell: The Suspects Emerge

Police Action:
- House in Wilbur searched; basement reeked of bleach but appeared clean.
- Apartment contained unusual items: shackles, 20+ phones, 56 Beanie Babies (21:35).
- Persons of interest identified: Aubrey Trail (51), Bailey Boswell (23) – both disappear before they can be questioned (21:47–22:18).
Online Behavior:
- Aubrey and Bailey post a bizarre 9-minute Facebook livestream, denying involvement but admitting they met Sydney (“I just want the family to know I am truly sorry. I didn’t have anything to do with this. I hope Sidney is found. She is a sweet, amazing girl.” - Bailey, 33:11).
- Aubrey’s sinister admission: “I’m a crook, I’m a thief. Have been my whole life. But I’m not what you are trying to make me out to be. I’ve never killed anyone in my whole life.” (31:04)

6. Details of the Manhunt and Other Victims

Flight & Live Updates:
- Aubrey and Bailey flee Nebraska, hop from motel to motel using burner phones (37:58).
- Travel with another woman, Caitlin, whom they threaten and try to coerce into a bizarre plot (34:32-37:56).
- Caitlin escapes, supplies police with crucial information, but timing of her contact is unclear (38:36).
Their Arrest:
- FBI tracks down duo via the Facebook livestream digital trail to Branson, Missouri; arrested November 30, 2017 (39:13).

7. Digital Trail & Discovery of Remains

Location Data:
- Using cell phone records from Bailey and Aubrey, police search rural Clay County.
- December 4, 2017: Human body parts in black trash bags found over an hour from Wilbur (41:56).
- 14 pieces recovered; not all remains found (42:37).
- Alongside remains: sex toys, cat leash, Sidney’s clothes, tarps, men’s underwear, women’s boots, and stained clothing (43:54).
- Forensic evidence: strangulation, restraints, bruises, post-mortem dismemberment (45:04).
Quote Highlight:
- Captain (46:14): “One thing about this ruse, we’re going to get on a dating website... That will drop your guard a little bit, little trust... And all of this was just a ruse to find a victim?”

8. The Digital Setup and Execution

The Catfish:
- Bailey (“Audrey”) and Aubrey target Sydney over Tinder, never revealing Bailey’s relationship with Aubrey (47:06).
- Exchanged 140+ messages before first date; planned and executed violent crime after gaining Sydney’s trust (47:06–48:00).
- Day of crime: Aubrey surveils Sydney at her workplace, duo buy tools and cleaning products in advance (48:00-49:16).
Timeline:
- Bailey texts Sydney: “I’m outside” at 6:54pm; her phone is powered off at 8:32pm after arriving at Wilbur (50:24–51:22).
- Likely ambush; trauma and restraint marks on Sydney’s body align with this theory.
- Remains transported and scattered in rural locations next day.

9. Aftermath & Investigation Realities

Physical Evidence and Clean-Up:
- Massive bleach clean-up effort in the basement, to the extent that the upstairs owner becomes physically ill from fumes (53:30).
Public and Police Encourage Transparency Online:
- Noted importance of leaving digital footprints and telling friends about plans – may have made the difference in finding suspect quickly.
- Captain (17:24): “If there’s one thing people should take away from this case, tell people what you… what’s going on in your life. She talks to her friends, and that… gives us some leads...”

10. Conclusion and Teasers for Part Two

Episode ends with the crime scene processing, connections between digital evidence, cell phone records, and the anticipation of the courtroom battle and further insights into the mindsets of Aubrey Trail and Bailey Boswell (54:19).
Sign-off Quote:
- Nick (54:24): “Until then, be good, be kind and don’t litter.”

Notable Quotes & Timestamps

Nick (02:32): “It was November 15, 2017 and 24 year old Sydney Loofe was excited. She was going on a second date with someone she liked very much... But unfortunately, that's not what happened. Sydney did not call or text. Sydney did not come home.”
Captain (08:29): “You don't know how that drug is going to affect your daughter...”
Nick (11:16): “It was evident that Sidney, or at least her phone, got to this location 40 miles away via someone else.”
Susie Loofe (Facebook post, relayed by Nick at 16:13): "We're asking for you to please continue to share these posts and pray for her safe return."
Captain (19:45): “This is very smart.” (on Brooklyn’s Tinder sting).
Aubrey Trail (31:04): “I'm a crook, I'm a thief. Have been my whole life. But I'm not what you are trying to make me out to be. I've never killed anyone in my whole life.”
Bailey Boswell (33:11): "I just want the family to know I am truly sorry. I didn't have anything to do with this. I hope Sidney is found. She is a sweet, amazing girl."
Captain (46:14): “...all of this was just a ruse to find a victim?”

Important Timestamps

02:32 – The last night Sydney is seen and her background.
06:55 – Sydney's mental health history and family’s concerns.
10:46 – Police trace Sydney’s phone to Wilbur, a key lead.
13:57 – Friends produce Snapchat and Tinder evidence of Sydney’s last planned date.
19:45–21:24 – Brooklyn’s Tinder sting to identify the suspect.
21:47 – Named suspects Aubrey Trail and Bailey Boswell announced.
29:29–33:22 – Aubrey and Bailey address public in Facebook livestream.
41:56 – Discovery of remains in Clay County.
45:04 – Details of autopsy and dismemberment.
50:24 – Timeline during the night of Sydney’s disappearance and forensic deductions.

Closing Thoughts

With their investigative rigor, Nic and the Captain reveal the unfolding threads of deception, digital footprints, and chilling violence that characterized Sydney Loofe’s case. The episode’s meticulous attention to both the victim’s humanity and the complexity of the investigation sets the stage for the unraveling of one of Nebraska’s most haunting modern crimes. Part 2 is teased to dive deeper into the “why” and the subsequent legal proceedings.

For more in-depth analysis and continued discussion of the Sydney Loofe case, don’t miss Part 2.

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Transcript

The Captain (0:00)

SA.

Nick (0:39)

Welcome to True Crime Garage, wherever you are, whatever you are doing. Thanks for listening. I'm your host, Nick, and with me, as always, is a man who is a traveler of both time and space. Here is the captain.

The Captain (0:52)

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

Nick (1:00)

Today we are going to go dark and get out of this sun. We are drinking Moonlit by the adventurous brewers over at New Trail Brewing. Moonlit is an imperial stout brewed with plenty of dark and English pale malts. This is a highly decadent stout, ABV 9.1%. So drink this one at home in your garage. Our garage beer grade is 4 out of 5 bottle caps. All right, let's give some thanks and praise to our good friends that helped us fill up the old garage fridge. First up, a cheers to Jen in the dark Ozarks of Arkansas.

The Captain (1:42)

And a big we like your jib goes out to Candace from Williamston, South Carolina. And a big tall cans in the air to Katisha Doyle from Tasmania, Australia. From your very clueless husband, Adam. Very clueless, but very persistent. We like your jib.

Nick (1:59)

Next we have a big Texas cheers to Cameron Gross in Houston. And last but certainly not least, we have Kelly Muncie in Defiance, Ohio. Everyone we just mentioned, they went to true crimegarage.com and helped us out with this week's beer fund. And for that, we thank you.

The Captain (2:18)

Yeah, BWR you and beer run. Make sure you go to truecrimegarage.com sign up on the mailing list. I will be sending out a promo code this week so you can get a discount on everything in the merch store. And that's enough of the business.

Nick (2:32)

All right everybody gather round. Grab a chair, grab a beer. Let's talk some true crime. It was November 15, 2017 and 24 year old Sydney Loof was excited. She was going on a second date with someone she liked very much. She sent a Snapchat to a close friend which was a photo of her face and shoulders with the caption ready for my date? Sydney went on the date. Her friend expected to hear from her afterward to hear all about how much she liked the person and that it went as well or better as their first date. But unfortunately, that's not what happened. Sydney did not call or text. Sydney did not come home. This is True Crime Garage. Sydney Loof was born on August 21st first 1993 in Broken Bow, Nebraska to parents George and Susan. She has a younger sister, Mackenzie, and an older brother, Levi. Her father George was the assistant football coach and the principal at NEI Oakdale High School where Sydney's mother was a special education teacher. Both parents were very involved in the community and Sydney had the benefit of having involved caring parents. The family was very close with movie nights, Christmas Eve sleepovers, bike rides, church and so on. Sidney was in a church youth group and was an excellent fisherman and was involved in band, Future Business Leaders of America and played golf, volleyball and basketball in high school until a devastating scoliosis diagnosis sidelined her. As a result of this condition, she had a distinctive walk, but she made the best of it, graduating from high school in 2011, where her teachers saw her as responsible, quiet and diligent. Two years later, Sydney moved to Lincoln where she worked at Menards. Now Menards is a DIY type of big box store. There she made very good friends and was considered to be one of the kindest, most polite cashiers. She was the kind of person who took people in when they were struggling to pay their rent or between places to live. She helped out three different co workers. In this way, Sidney hoped to start a family of her own. But that dream sadly would not come to fruition. By 2017, it seems Sydney was not in a great place personally. First of all, Menards was not her dream job. As much as I like the store, it was not her career. She wanted to work in a veterinary clinic and she was actively job hunting around this time. But it was also more than that. Captain right. Her mom, Susie told the media that Sydney had some mental health struggles. Specifically she had anxiety and depression and she had been managing these conditions since high school. But it was getting worse. But then she vanished. In fact, the very week that Sidney disappeared, her mom took her to a doctor's appointment in Lincoln, Nebraska. This to obtain a new prescription for antidepressants. This was the last time that Susie saw her daughter alive.

Nick (21:35)

This couple presented themselves as antique dealers. When police entered the apartment in the basement of the home, they found everything was neat and tidy, but it reeked of bleach. And even when police returned the following day, this time armed with a search warrant, they found nothing necessarily incriminating. Later, when the apartment was cleaned out, among the Items collected were 56 Beanie Babies, Antique toys, a lion rug, a pair of shackles, and over 20 phones. Then, on November 28, we've got some big news. Two people were publicly named persons of interest in Sydney's disappearance. Police named them publicly because they could not find them and needed the public's help in tracking them down. Lincoln PD said they are asking for the public's assistance searching for Aubrey Trail, 51 years old. Trail is 6ft tall, 284 pounds with brown hair and blue eyes. And Bailey Boswell, age 23. Boswell is 5ft 8 inches tall with brown hair and hazel eyes. Lincoln PD said. The two people have connections in multiple states. 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. IXL is an award winning online learning platform that helps kids truly understand what they're learning through fun, engaging and personalized content. IXL is used in 96 of the top 100 US school districts and is the perfect tool to keep learning going without making it feel like school. I love ixl. You're going to get the results that you want. I did tutoring when I was a kid and it was incredibly inconvenient. You had to get a date, a time, a location, a ride. IXL is incredibly convenient because it's online and it's a fraction of the price of traditional services. Make an impact on your child's learning. Get IXL now and True Crime Garage listeners can get an exclusive 20% off IXL membership when they sign up today at ixl.com garage. That's ixl.com garage to get the most effective learning program out there at the best price. You know what doesn't belong in your epic summer plans? Getting burned by your old wireless bill. While you're planning beach trips, barbecues and three day weekends, your wireless bill should be the last thing holding you back. Make the Switch to Mint Mobile With Mint, you can get the coverage and speed you're used to, but for way less money. And for a limited time, Mint mobile is offering three months of unlimited premium wireless service for 15 bucks a month. So while your friends are sweating over data, overages and surprise charges, you'll be chilling. Literally and financially. I have had many cell phone service providers over the years and I can tell you if you make the switch to Mint Mobile or one of two things is going to happen. Either you will get better, more reliable service than you currently have and save a bunch of money. Or you'll get the same quality of service that you currently have and save a bunch of money. Either way, you win this year. Skip breaking a sweat and breaking the bank. Get this new customer offer and your three month unlimited wireless plan for just 15 bucks a month at mintmobile.com tcg that's mintmobile.com tcg upfront payment of $45 required equivalent to $15 a month limited time new customer offer for first three months only. Speeds may slow above 35 gigabytes on unlimited plan taxes and fees. Extra cement Mobile for details, this message is sponsored by Greenlight. In every crime we cover, money is an invisible thread. Sometimes the motive, the trigger, or even the desperation that pushes someone over the edge. Financial stress can turn ordinary people into criminals. And a lack of financial literacy makes victims more vulnerable. That's why teaching kids about money isn't just smart, it's essential. Greenlight is a debit card and money app for kids and families. It's a safe way to teach kids and teens about money, preparing them for bigger financial decisions later. Give your kids the financial education many of us didn't get. Join millions of parents already using Greenlight, the number one family finance and safety app. Greenlight is fantastic. They do not teach your kids about finances at school. That's something that the parents have to do. That's your job. It's 2025. Don't hand your kid cash. Give them green light. I have friends that use green light with their sons so their sons can set goals, save their money, and parents can keep an eye on their spending. Have your kids set some goals, save up for something, and then they get rewarded when they make that awesome purchase. Start your risk free Greenlight trial today@greenlight.com garage. That's greenlight.com garage to get started. Greenlight.com garage.

Nick (28:25)

Yeah, they cannot locate this couple. They've been to the apartment at least twice. You know, they return with the search warrant and then publicly announce that they're looking for these two individuals and that they, they publicly say that they're persons of interest in this missing persons case. Diving into some of the details of this and we're going to try to sort this out the best we can because remember, we have Tara and Brooklyn who are Sidney's friends and they're the ones that inform police that the date was with this so called Audrey. And now police are looking for two people, but they're not looking for anyone named Audrey. They're looking for an Aubrey who's not a woman, he's a man. And they are looking for Bailey Boswell. And this has to lead back to the date even though the, the names are not lining up. So once, once they got the name Audrey and the phone number from Brooklyn police investigated this Audrey. A Lincoln detective called the number and after a couple of tries got Audrey to call him back. This air quotes Audrey was evasive saying she didn't want to talk to the police because she had warrants and did say that she had gone on a date with Sidney but had actually dropped her off at a friend's house in Wilbur afterwards. But a little, yeah, a little digging by police into this Audrey revealed that her name was not Audrey at all. It was in fact Bailey Boswell. Her Tinder date with Sydney was confirmed by social media post made by Bailey and 140 plus messages on the Tinder app between Bailey and Sydney. In one of the final Tinder messages confirming their first date on the 14th, Sydney messaged Audrey just going to be me and you, right? Okay. Yes, of course, responded Audrey. Police tried to talk to this Audrey slash Bailey person but she was missing in action. Police declared her and her 51 year old boyfriend Aubrey Trail also missing in action, official persons of interest. The two apparently split town immediately after they were labeled as such.

Nick (39:13)

Right place. And if they're moving city to city, then state to state, it still leaves them. Leaves law enforcement behind. But see, the FBI, they're able to use that Facebook live stream video to hone in on the digital source because they're using these phones. But the Facebook livestream video, they. They used a phone registered to Bailey Boswell. That phone had called a number at the Windmill Inn in Branson, Missouri. Naturally, you're going to go there hoping to either A, find this couple there or B, sitting there waiting for them when they arrive. And that is where the two of these, the two will be arrested on November 30th. So they're nabbed on federal persons of interest warrants as well as charges unrelated to Sidney Luff's case. Completely. So Aubrey was wanted for possession of a firearm by a felon. Bailey was wanted on failure to appear on a minor drug charge in Lincoln, Nebraska. When the two were arrested, found in their possession were maps, hiking and camping gear, a supply of bottled water, sleeping bags, and so on. Every indication is that they were on their way to Mexico. Bailey and Aubrey agreed to speak with police investigating Sidney's case. The short of it is they're going to stick to their story that was on the live stream video that Sidney was last seen by them alive and well in Wilbur Bailey had dropped her off at someone's house and went about her life. She had no idea what happened to Sydney. Neither did Aubrey. You know, at the top of the show, we were giving out some toast. I should probably mention here a shout out. That is in order. We. We could not have written this episode without the incredible reporting by the Grand Island Independent in cooperation with the Lincoln Journal Star and the Omaha World Herald, all on Omaha.com's website. Using phone tracking information from two of Bailey's cell phone accounts and a flip phone registered to Aubrey, Lincoln police Detective Bob Hurley and the FBI tracked the movements made by the phones on Wednesday, November 15th and Thursday. Thursday, November 16th. So keep in mind this is, this is at the time when Sydney is first missing, right? This is 14 to 15 days before the two who are seemingly on the run are apprehended in another state. They looked at the pings and considered the length of time it appeared the phone spent in different locations. They started looking at a very specific location, then methodically did a foot search 25 miles of remote roadways using cadaver dogs. So Sidney's missing. Two weeks later, these two are apprehended. Who said they had nothing to do with her? Even though it appears at least Bailey may have been the last person to see Sydney. But then it's on December 4th. Body parts were found in and spilling out of black trash bags scattered in overgrown ditches along a gravel road outside of Edgar. This is in rural Clay County. The location was an hour's drive from Wilbur and had been visited by Bailey's and Aubrey's phones on November 16. Then more remains were found the following day. The total number of body parts recovered was 14. The body was not complete and upper arm was never located. And it was Jesus at the time. Obviously it's not yet confirmed to be Sydney, but the cops were pretty much, yeah, sure that she had been disposed of. And a lot of this, basing a lot of this on phone locational data.