Search Captions & Ask AI

Sydney Loofe /// Part 1 /// 864

August 19, 2025 / 54:44

This episode covers the disappearance of Sydney Lof, her mental health struggles, and the investigation into her case. Key discussions include her last date with Audrey, the involvement of Bailey Boswell and Aubrey Trail, and the discovery of Sydney's remains.

Sydney Lof, a 24-year-old from Nebraska, went missing on November 15, 2017, after a second date with a woman named Audrey. Friends and family became concerned when Sydney did not return home or show up for work. Her parents reported her missing when they found her apartment in disarray, with her cat unfed and her personal belongings left behind.

Police traced Sydney's last known location to a ping from her phone in Wilbur, Nebraska. They learned that she had been communicating with Bailey Boswell, who had been using the name Audrey on Tinder. Bailey and her boyfriend, Aubrey Trail, became persons of interest after their connection to Sydney was established.

After an extensive search, Sydney's dismembered remains were found in rural Clay County, leading to further investigation into Bailey and Aubrey's actions following Sydney's disappearance. The episode details the timeline of events, including the couple's attempts to evade law enforcement.

The episode highlights the importance of mental health awareness and the dangers of online dating, as well as the investigative efforts that led to the eventual arrest of Bailey and Aubrey.

TLDR

Sydney Lof vanished after a date; her remains were later found, leading to the arrest of Bailey Boswell and Aubrey Trail.

Episode

54:44
00:00:06
[Music] Welcome to True Crime Garage. Wherever you are, whatever you are doing, thanks
00:00:44
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
00:00:52
the captain. >> Yeah, it's good to be seen and good to see you. Thanks for listening. Thanks
00:00:56
for telling a friend. >> Today we are going to go dark and get out of this sun. We are drinking
00:01:06
Moonlight by the adventurous brewers over at New Trail Brewing. Moonlight is an Imperial stout brewed with plenty of
00:01:14
dark and English pale malts. This is a highly decadent stout, ABV, 9.1%. So, drink this one at home in your garage.
00:01:25
Our garage beer grade is four out of five bottle caps. All right, let's give some thanks and praise to our good
00:01:34
friends that helped us fill up the old garage fridge. First up, a cheers to Jen in the dark Ozarks of Arkansas. And a
00:01:43
big we like your jib goes out to Candace from Williamston, South Carolina. And a
00:01:47
big tall cans in the air to Katisha Doyle from Tasmania, Australia from your very clueless husband, Adam. Very
00:01:56
clueless, but very persistent. We like your jib. Next, we have a big Texas cheers to Cameron Gross in Houston. And
00:02:04
last, but certainly not least, we have Kelly Muny in Defiance, Ohio. Everyone we just mentioned, they went to
00:02:11
trueimegrage.com and helped us out with this week's beer fund. And for that we thank you.
00:02:18
>> Yeah. BW are ruining beer run. Make sure you go to true crimegar.com. Sign up on
00:02:23
the mailing list. I will be sending out a promo code this week so you can get a discount on everything in the merch
00:02:30
store. And that's enough of the business. All right, everybody. Gather around, grab a chair, grab a beer. Let's
00:02:36
talk some True Crime. [Music] [Music] It was November 15th, 2017, and 24year-old Sydney Lof was excited.
00:03:13
She was going on a second date with someone she liked very much. She sent a Snapchat to a close friend,
00:03:21
which was a photo of her face and shoulders with the caption, "Ready for my date." Sydney went on the date. Her
00:03:30
friend expected to hear from her afterward, to hear all about how much she liked the person, and that it went
00:03:38
as well or better as their first date. But unfortunately, that's not what happened. Sydney did not call or text.
00:03:48
Sydney did not come home. This is true crime garage. [Music] [Music] Sydney Lof was born on August 21st, 1993
00:04:19
in Broken Bow, Nebraska to parents George and Susan. She has a younger sister, McKenzie, and an older brother,
00:04:27
Levi. Her father, George, was the assistant football coach and the principal at Nei Oakdale High School,
00:04:36
where Sydney's mother was a special education teacher. Both parents were very involved in the community, and
00:04:43
Sydney had the benefit of having involved, caring parents. The family was very close with movie nights, Christmas
00:04:50
Eve sleepovers, bike rides, church, and so on. Sydney was in a church youth group and was an excellent fisherman and
00:04:59
was involved in band, Future Business Leaders of America, and played golf, volleyball, and basketball in high
00:05:06
school until a devastating scoliosis diagnosis sidelined her. As a result of this condition, she had a distinctive
00:05:15
walk, but she made the best of it, graduating from high school in 2011, where her teachers saw her as
00:05:22
responsible, quiet, and diligent. Two years later, Sydney moved to Lincoln where she worked at Menards. Now,
00:05:31
Menard's is a DIY type of big box store. there. She made very good friends and was considered to be one of the kindest,
00:05:41
most polite cashiers. She was the kind of person who took people in when they were struggling to pay their rent or
00:05:49
between places to live. She helped out three different co-workers in this way. Sydney hoped to start a family of her
00:05:57
own, but that dream sadly would not come to fruition. By 2017, it seems Sydney was not in a great place. Personally,
00:06:08
first of all, Menard's was not her dream job. As much as I like the store, it was
00:06:13
not her career. She wanted to work in a veterary clinic and she was actively job
00:06:20
hunting around this time. But it was also more than that, Captain. Her mom Susie told the media that Sydney had
00:06:27
some mental health struggles. specifically. She had anxiety and depression, and she had been managing
00:06:33
these conditions since high school, but it was getting worse. But then she vanished. In fact, the very week that
00:06:41
Sydney disappeared, her mom took her to a doctor's appointment in Lincoln, Nebraska. This to obtain a new
00:06:48
prescription for anti-depressants. This was the last time that Susie saw her daughter alive. Yeah, we talk about
00:06:56
this topic a lot, mental health, especially in your late teens and early 20s, but every anti-depressant
00:07:06
has some side effects, and that affects everybody differently. And so, she was going down this journey to figure out
00:07:13
what medication was going to work best for her. It's trial and error in a lot of those cases. Let's go to Thursday,
00:07:20
November 16th. Sydney did not show up for her regular shift at Menard's. She didn't tell her friends and family that
00:07:27
she was skipping work and her phone, well, it's going straight to voicemail. This was unheard of for Sydney. She was
00:07:36
very responsible, very workoriented. Her worried co-workers and friends of Sydney's called her sister McKenzie, who
00:07:46
they knew as well. And then in return, her sister calls the parents. So George and Susie called and text, here's one of
00:07:55
the texts from Susie to Sydney that read, "Please, Sydney, you're scaring me." By 5:00 p.m. on the 16th of
00:08:03
November, George and Susie had reported their daughter missing to the Lincoln, Nebraska Police Department. Well, this
00:08:10
would be extra scary for a parent because you know that she's now taking a new drug and how is that drug going to
00:08:19
affect her daughter? You don't know. And some of these anti-depressants can make
00:08:25
people suicidal even if they weren't suicidal before. >> On Friday, the following day, they
00:08:31
decided to go to her apartment. This is a 2-hour drive for them. It's not clear whether they had a key or if the
00:08:37
landlord let them in. But they do get access to the apartment. Once inside, they're saying, you know, nothing seems
00:08:45
a miss here with the exception of three things. One, Cydney's cat, Mimsy, had no
00:08:52
food or water and appeared to be hungry, so this would be not common. Two, Cydney's car was parked outside of her
00:09:00
apartment. Three. Sydney's glasses and purse were in the apartment as well, and the lights were left on. The car and
00:09:09
purse and glasses of course are going to be startling. You're you're expecting to
00:09:14
if you don't find your daughter, you're expecting to not find the car would be would be the scenario here when you're
00:09:20
arriving. >> Exactly. And again, she didn't show up for work and she's not answering her
00:09:25
phone. And I think the other problem is Okay, so you get there, you see the car.
00:09:29
Okay, the cat's hungry. No big deal. Maybe she went on a walk or maybe she's out with somebody, but after 30 minutes
00:09:37
to an hour or so, you have to be thinking the worst at this point. And this will be the same day that things
00:09:44
are going to go from 0 to 60 very quickly in this case because we have after the parents visit the apartment.
00:09:54
Lincoln police issued a statement that they didn't know for sure that Sydney was in any real danger, but they wanted
00:10:01
to check on her welfare given her aw status. the police here are reaching out to the public to look for
00:10:11
this young woman. And if they're doing that this quickly, I have to you have to believe that there's something there
00:10:19
telling them to do this cuz this doesn't seem to be standard police protocol. Not
00:10:23
only had Sydney vanished without her car and her personal items, left the cat unfed, but her bank account was
00:10:30
untouched, and police IT personnel verified that Sydney's phone had been powered off. So, they're doing some work
00:10:38
behind the scenes to figure some of this stuff out to confirm that, you know, she's off the grid. She's gone dark
00:10:46
here. >> Question for you. Does this mean that they know somebody shut the phone off or
00:10:51
is it just her phone is off and we don't know if somebody turned it off or if the
00:10:56
battery's dead? >> The statement is that it had been powered off. Now I I don't I don't think
00:11:03
that there would be clear indication of >> why >> what method was used to do that but I
00:11:09
but the one of the problems here is her normal life her her daily she was always
00:11:17
on Snapchat posting stories according to friends and family. So, she's one of those types that like if she's not
00:11:24
posting anything, it's a safe assumption to assume that the the phone is off or she's sleeping or something of that
00:11:31
nature. But we have law enforcement, IT personnel that have determined bank accounts not being activated or accessed
00:11:39
and the phone is is off and not being used. And then they track her phone through her cell phone provider and
00:11:47
found that the last ping before her phone was turned off was a tower in Wilbur, Nebraska, which is about 40
00:11:54
miles away from Sydney's apartment. Immediately, the reaction is, hey, there's no reason for this young woman
00:12:01
to be in this tiny town. She knows no one there. Plus, they find her car at home. It was
00:12:07
evident that she that Sydney or at least her phone got to this location 40 miles
00:12:14
away via someone else. Yeah. I think some of the confusing things especially for these cases when we have a young
00:12:22
adult. They're not living with their parents. The parents don't know every detail of their daughter or son's life.
00:12:29
They don't know their weekly schedule at that point. Like you said, she's she was
00:12:34
posting a lot to Snapchat. She missed work. She hasn't fed her cat. Her car is there. But there's one good thing about
00:12:42
her posting on Snapchat. She posted that she was going to go out on a date. >> Yeah. The local media was reporting a
00:12:52
heavy police presence at a home near the 600 block of West 7th Street. This was a
00:12:59
home that was owned by a husband and wife who were in their 60s at this time. Police wouldn't comment on what they
00:13:05
were doing there or why they were there other than acknowledging that they were looking for a missing person whose final
00:13:13
phone ping was in Wilbur. So, it was a quick connection to the missing person Sydney case from the onlookers. Police
00:13:24
had quickly learned that they needed to talk to someone specific, someone who may have been the last person to see or
00:13:32
hear from Sydney. So, getting into what you're talking about here, Captain with the Snapchat, her friend Tara was able
00:13:40
to produce a text from Sydney that was sent to her on that Wednesday. And like you said, she was raving about a date
00:13:50
that she had gone on on Tuesday night. She and her date were going to see each other again on that Wednesday evening.
00:13:57
>> Her and her date dummy. >> On that Wednesday, Sydney went to Snapchat, sent her friend Tara a photo
00:14:04
of herself that was captioned, "Ready for my date." Right? >> Tara had either screenshotted this or
00:14:11
saved it in their chat, which is how she was able to show the police. She showed
00:14:18
the this to the police. Police needed to talk to whomever Sydney had planned to meet on that Wednesday night because
00:14:24
their trail for her ends there. They're tracing, retracing her steps, tracing her movements, and this is where it
00:14:35
ends. So now we need to figure out who this person was and communicate with them. They learned from Tara that it was
00:14:42
a woman that Sydney had met online named Audrey, someone Sydney called her dream
00:14:47
girl. The two had a very successful first date, like we said, and Sydney was excited to see her again on Wednesday
00:14:56
night. But police were mum about the details, confirming only that they had actually spoken to this date. But
00:15:03
Sydney's father, George, told local news, "We are afraid that she has been abducted."
00:15:08
>> Yeah, I think she was pretty open. Sydney was pretty open with her friends that she was on Tinder, I believe, and
00:15:16
that she was, you know, seeking out dates through Tinder. The police released a description of Sydney, 5'7 in
00:15:23
tall, 135 lbs, blonde, last seen wearing a white Columbia jacket and a cream blouse. The family also released some
00:15:33
photos of Sydney's tattoos, hoping they might help someone recognize her. My Antelopee County News reported,
00:15:43
quote, "We feel that she could be anywhere, so we've decided to post her tattoos because they're easily
00:15:50
recognizable. Please let us know if you have any information that may be useful in
00:15:57
locating her. We're asking for you to please continue to share these posts and pray for her safe return. Thank you for
00:16:06
all of your kind thoughts and prayers. This was from Susie Lof, her mother. >> I see a lot of similarities between
00:16:15
Sydney and Amy Bradley. I understand the c the circumstances are different, but I
00:16:22
see similarities as far as victimology. >> They're similar in age as well. And like
00:16:27
you said, there are some things that that match up in both of those cases as far as victimology goes. Susie also
00:16:35
posted on Facebook, "We just wanted to let everyone know that Sydney still hasn't returned home despite outstanding
00:16:42
efforts by the Lincoln and Wilbur police departments. We've had very few leads, but haven't lost our hope that she will
00:16:49
return safely soon." Sydney's friends organized a vigil, desperate to bring attention to her case. In her hometown,
00:16:58
green light bulbs and ribbons sprang up on porches and trees. By the 21st of November, with nothing from Sydney in
00:17:07
five days, Susie Lof told WOWT that she was having a hard time putting her feelings into words. Of course, the
00:17:16
lack of any new information must have been incredibly devastating, frustrating, and disheartening for Susie
00:17:23
and the the rest of the family. >> But if there's one thing that people should take away from this case, tell
00:17:28
people what you what's going on in your life. She talks to her friends about that she's seeking dates through Tinder.
00:17:35
She is posting a lot of her activities on Snapchat. And that might seem a little silly to some, but these are
00:17:43
going to give us some leads because it's not a situation where it's just Sydney didn't show up for work and we have no
00:17:50
clue about her whereabouts or what she was planning on doing. We at least know. And you and even though she's been
00:17:57
missing for 5 days, like you said, at this point, you go, "Well, we know that she was planning to go on a date with
00:18:04
somebody." That is a solid lead, and we now have to talk to that person, scrub that person for information, and
00:18:12
and to see, did they go on the date? If so, where did they go? Yeah. Both the Lincoln Police Department and the Selen
00:18:20
County Sheriff's Office worked the missing person's investigation along with Nebraska State Patrol, the US
00:18:26
Marshalss, and the FBI. So, we have a big presence here, a collaboration of work being done by these different
00:18:33
agencies. Searches for Sydney were intensive. Ponds were being drained. Every inch of Wilbur was being searched.
00:18:43
Meanwhile, Sydney's family raised money for a billboard near Interstate 80 with photos of their daughter and their
00:18:53
information. There was also a name page that was set up rather quickly, two Facebook pages, and lots of local media
00:19:01
coverage that would begin to fan out from there. Sydney had snapped her friend Brooklyn Mcrist about her second
00:19:10
date with Audrey. She'd sent Brooklyn a snap with a photo of an attractive brunette and her Tinder profile, which
00:19:20
said that Audrey was her name and she was 32 miles outside of Lincoln. Brooklyn got on Tinder and created a
00:19:27
profile for herself that indicated that she liked women. She used the same hashtags or interest, whatever people
00:19:36
use on Tinder to find dates. She's using all the same stuff that Sydney had in her profile. So, she's trying to mimic
00:19:43
Cydney's profile as much as she can. >> This is very smart. >> Yeah. She specifically made an account
00:19:49
to try to match with this Audrey person. And indeed, this fishing expedition worked. Audrey found her and Brooklyn
00:19:58
was able to message her and get her phone number. She learned that she hailed from Missouri and she worked at a
00:20:06
financial institution. according to her profile. Anyway, >> you can be whoever you want to be
00:20:11
online. >> Yeah, there's a lot of people that are doing that on the streets of the country
00:20:17
as well. Uh and look, and it creates a a whole huge long list of problems. >> Yeah, definitely. But if I was going to
00:20:27
create a character online, I mean, first his name would be the captain, but I'd also my occupation
00:20:34
would be starting point guard for the Chicago Bulls. >> Yeah, cuz there's no way for people to
00:20:41
figure out if that's incorrect. The vigilant friend Brooklyn fed all of this information to the cops. Mhm.
00:20:51
>> Police days before learned that the phone ping in Wilbur, approximately 30 m from Lincoln or so. And guess what?
00:20:59
Bingo bango jingo jango. Audrey lived there and she lived there with her boyfriend.
00:21:06
>> Yes. >> Investigators went to the home where the couple were renting a basement. So they
00:21:11
basically had a basement apartment that they were renting. This has got to be from that 60-year-old couple that we had
00:21:18
mentioned earlier. The couple had lived in this home since June of 2017. >> Yeah. But I think that shows you the
00:21:27
technology that they got a ping on this house, not not just within that area. >> This couple presented themselves as
00:21:38
antique dealers. When police entered the apartment in the basement of the home, they found
00:21:45
everything was neat and tidy, but it rire of bleach. >> And even when police returned the
00:21:53
following day, this time armed with a search warrant, they found nothing necessarily incriminating. Later, when
00:22:00
the apartment was cleaned out, among the items collected were 56 Beanie Babies, antique toys, a lion rug, a pair of
00:22:10
shackles, and over 20 phones. Then on November 28th, we've got some big news. Two people were publicly named persons
00:22:21
of interest in Sydney's disappearance. Police named them publicly because they could not find them and needed the
00:22:28
public's help in tracking them down. Lincoln PD said they are asking for the public's assistance searching for Aubrey
00:22:40
Trail, 51 years old. Trail is 6 feet tall, 284 lbs with brown hair and blue eyes. And Bailey Boswell, age 23.
00:22:50
Boswell is 5'8 in tall with brown hair and hazel eyes. Lincoln PD said the two people have connections in multiple
00:23:01
states. You may think that feeling safe at home means having good locks and alarm that
00:23:15
makes loud noises, but the truth is true security takes more. With Simply Safe's
00:23:20
new active guard outdoor protection, you get a system that works to prevent that
00:23:25
break-in, that violation of your space from ever happening in the first place. AI powered cameras, plus live monitoring
00:23:33
agents, detect suspicious activity around your property. If someone's lurking, agents talk to them in real
00:23:40
time, turn on spotlights, and can call the police, proactively deterring crime before it starts. Of course, a home or
00:23:50
business property alarm system should react to a break-in or a crime. Simply safe systems prevent the crime or the
00:24:00
break-in from ever happening in the very first place. Now, that is protection. That is being completely safe. Visit
00:24:09
simplysafe.com/gage to claim 50% off a new system with a professional monitoring plan and get
00:24:16
your first month free. That's simplysafe.com/g. There's no safe like simply. Summer's winding down and whether your
00:24:26
kids are just soaking up the last few weeks or already asking when school starts, this is the perfect time to ease
00:24:33
back into learning with. Il is an awardwinning online learning platform that helps kids truly understand what
00:24:43
they're learning through fun, engaging, and personalized content. ISL is used in
00:24:49
96 of the top 100 US school districts and is the perfect tool to keep learning going without making it feel like
00:24:57
school. I love you're going to get the results that you want. I did tutoring when I was a kid
00:25:05
and it was incredibly inconvenient. You had to get a date, a time, a location, a
00:25:11
ride. L is incredibly convenient because it's online and it's a fraction of the price of traditional services. Make an
00:25:20
impact on your child's learning. Getl now and True Crime Garage listeners can get an exclusive 20% offl membership
00:25:29
when they sign up today atl.com/g. That's.com/g to get the most effective learning
00:25:38
program out there at the best price. This message is sponsored by Greenlight. In every crime we cover, money is an
00:25:46
invisible thread. Sometimes the motive, the trigger, or even the desperation that pushes someone over the edge.
00:25:53
Financial stress can turn ordinary people into criminals. And a lack of financial literacy makes victims more
00:26:00
vulnerable. That's why teaching kids about money isn't just smart, it's essential. Greenlight is a debit card
00:26:07
and money app for kids and families. It's a safe way to teach kids and teens about money, preparing them for bigger
00:26:14
financial decisions later. Give your kids the financial education many of us didn't get. Join millions of parents
00:26:22
already using Greenlight, the number one family finance and safety app. Greenlight is fantastic. They do not
00:26:29
teach your kids about finances at school. That's something that the parents have to do. That's your job.
00:26:36
It's 2025. Don't hand your kid cash. Give them green light. I have friends that use green light with their sons so
00:26:44
their sons can set goals, save their money, and parents can keep an eye on their spending. Have your kids set some
00:26:51
goals, save up for something, and then they get rewarded when they make that awesome purchase. Start your risk-free
00:26:58
Greenlight trial today at greenlight.com/g. That's greenlight.com/g to get started. greenlight.com/g.
00:27:20
All right, we are back. Cheers, mates. Tall can hands in the air. Cheers to you, Colonel. Cheers to you, Captain.
00:27:26
So, let me get this straight. We have a cell phone ping to this house. There's owners of that house. They live
00:27:33
upstairs. We have a couple that lives in the basement. >> Mhm. >> We believe that the female is possibly
00:27:42
the individual that was talking to Sydney on Tinder and possibly went on a date with Sydney before. They searched
00:27:51
their house. You say it's clean. It's neat. They have some items. They claim they're antique dealers. They sound more
00:27:58
like garage sale dealers. But then these two individuals, this couple now are missing.
00:28:04
>> Yeah. They cannot locate this couple. They've been to the apartment at least twice. You know, they returned with the
00:28:11
search warrant and then publicly announced that they're looking for these two individuals and that they they
00:28:19
publicly say that they're persons of interest in this missing person's case. diving into some of the details of this
00:28:28
and we're going to try to sort this out the best we can because remember we have
00:28:32
Tara and Brooklyn who are Sydney's friends and they're the ones that informed police that the date was with
00:28:42
this so-called Audrey and now police are looking for two people but they're not looking for anyone named Audrey they're
00:28:50
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
00:28:58
to the date even though the the names are not lining up. So once once they got the name Audrey and the phone number
00:29:06
from Brooklyn, police investigated this Audrey, a Lincoln detective called the number and after a couple of tries got
00:29:15
Audrey to call him back. this air quotes Audrey was evasive, saying she didn't want to talk to the police because she
00:29:22
had warrants and did say that she had gone on a date with Sydney, but had actually dropped her off at a friend's
00:29:29
house in Wilbur afterwards. But a little >> Yeah, a little digging by police into
00:29:34
this Audrey revealed that her name was not Audrey at all. It was in fact Bailey Boswell. Her Tinder date with Sydney was
00:29:44
confirmed by social media post made by Bailey and 140 plus messages on the Tinder app between Bailey and Sydney. In
00:29:54
one of the final Tinder messages confirming their first date on the 14th, Cydney messaged Audrey. Just going to be
00:30:02
me and you, right? Okay. Yes, of course, responded Audrey. Police tried to talk to this Audrey/Bailey
00:30:10
person, but she was missing an action. Police declared her and her 51-year-old boyfriend Aubrey Trail, also missing an
00:30:19
in action, official persons of interest. The two apparently split town immediately after they were labeled as
00:30:26
such. >> That's not suspicious or anything. >> Oh, no. Aubrey and Bailey denied that
00:30:31
they had suddenly left Nebraska because they were on the run from the cops. Aubrey posted online, "As far as I know,
00:30:39
I'm not wanted for anything. I'm a person of interest and I'm not really running from anything." He said, "Well,
00:30:47
yeah. Well, listen to this." He says, "I'm this quotes from from Aubrey. >> I'm a crook. I'm a thief. Have been my
00:30:56
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." End
00:31:03
quote. Yeah. So, I've been a piece of [ __ ] my whole life, but um I didn't do this one.
00:31:08
>> From tracking their movements here, Captain, what they're doing is the two are they hastily leave town, which
00:31:17
cannot be a coincidence, >> right? >> They're out on the road. They're staying in cheap motel and they are working
00:31:24
their way down south. But these two like felt the need to talk about what was going on. In fact, they posted two the
00:31:34
two of them posted a 9-minute Facebook live stream complaining about being chased around by police like dogs. In
00:31:43
their live stream, a close-up video filmed in a vehicle. Aubrey said it was time for them to share their side of the
00:31:52
story. This video was posted for just about two hours before it was deleted >> and was posted on none other than the
00:32:01
Finding Sydney Lof Facebook page. So they they went right to the Sydney Lof Facebook page and posted this. In this
00:32:09
video, Bailey admitted to going on the date with Sydney, but said that she was innocent of any wrongdoing and that she
00:32:16
had simply driven around and smoked some pot. that the two they were hanging out,
00:32:20
driving around smoking pot. And she said, "I gave her a quarter ounce of really good weed. She asked me to drop
00:32:27
her at a friend's house. I did so. I have not heard from her since." She said the two women had planned to go to a
00:32:35
casino that weekend, but Sydney had never contacted her since then. Aubrey claimed he like chimes in during the
00:32:44
video. He's saying that he was praying Sydney would be found safe. And then Bailey concluded with quote, "I
00:32:52
just want the family to know I am truly sorry. I didn't have anything to do with
00:32:56
this. I hope Sydney is found. She is a sweet, amazing girl." Yeah. I don't know how much these two are antique dealers.
00:33:04
I I think they opened up a canning operation where they're canning tuna because this is fishy as fishy gets, my
00:33:13
friend. Well, and to add to it a little bit, like this this stream, this live stream.
00:33:20
>> Yeah, >> it looks like they're deliberately trying to obscure their faces, which is
00:33:26
all kinds of weird because, you know, we know who you are from the live stream, but I maybe it's possible that they're
00:33:32
on the run and their look is a little different at the time and they kind of want to keep it that way.
00:33:39
>> They want to voice it. They want to voice it out there and throw that out there, but they also don't want police
00:33:44
to catch up with them at the same time. >> What a guy have like 21 different charges against him.
00:33:50
>> That might be conservative. Yeah. >> In like a 50-year period, like you're a lifetime loser. You're a lifetime piece
00:33:58
of [ __ ] That's what you are. Of course, we're going to look at you. And by the
00:34:02
way, the cell phone ping puts her at your house. So this story of you driving around and smoking pot and you dropping
00:34:09
her off somewhere just doesn't make a lot of sense. >> Well, we know some of their movements
00:34:13
during this time, right? So Bailey and Aubrey travel to Omaha. They picked up a woman whom they say Bailey was seeing.
00:34:22
Her name is Caitlyn Brandell, but we'll learn more about Caitlyn and and some other people that they were associates
00:34:31
with. Let's say they had checked into a Holiday Inn at the Amerar Casino in Council Bluffs. They stayed until
00:34:40
November 19th using Caitlyn's vehicle for what they told her was a cocaine drop from a plane.
00:34:48
>> On Grand Island that would net them about 25K. >> Jesus. >> Surprise, surprise.
00:34:56
The drop never happened. Sorry, that's my impression. It's from a Pink Floyd album and the the cool folks will get
00:35:04
it. And there the three moved to onto Carney where Bailey and Aubrey wanted to abduct and kill an exchange student.
00:35:14
They told Caitlyn, we know this because Caitlyn tells us about this. They told Caitlyn that she had to participate or
00:35:22
Aubrey threatened her family. But at the motel in Carney, Caitlyn receives a message from the Lincoln Police
00:35:28
Department because her mother had filed a missing person's report on her. >> She's gone. Her car's gone.
00:35:35
>> Yeah. >> This seemed to scare the couple that were on the run, Bailey and Aubrey, who
00:35:41
told her that another young woman was missing and that Bailey was being falsely blamed because she was the last
00:35:49
person seen with this missing woman. According to this, Caitlyn, Bailey cried and insisted she did not hurt the
00:35:57
missing woman. Caitlyn left the duo and returned to her home. Smart move by Caitlyn.
00:36:04
>> Yeah, but let's pause for a second. Okay, so they're at this hotel motel Holiday Inn. Caitlyn's around these two
00:36:12
awful pieces of [ __ ] people. They're going to go to an island to get some cocaine that's going to be dropped
00:36:20
from a plane. And oh, by the way, you have to be involved in killing this exchange student. And if you don't,
00:36:28
we're going to harm your family. Bailey has the nerve to put on a Oscar winning performance of crying
00:36:38
and saying, "Well, there's this other girl missing and well, I have nothing to do with that." I mean, think about how
00:36:45
nuts that is. The the craziness that they're trying to get this girl involved in and then to have the the the nerve or
00:36:55
the balls or whatever to then cry and say, "We're not involved in this other stuff." There's no way that Caitlyn is
00:37:03
believing anything coming out of their mouths. >> Yeah. And it may not have had to have
00:37:08
been much of an act. I mean, you can spin it and say why you are crying or why you're upset, but she is very likely
00:37:17
crying because she knows that the police are after her, >> right, >> for a very serious crime, murder, and
00:37:26
they are closing in. And so I I think she's just spinning it. And you're absolutely right there, Captain. It's
00:37:33
It's pure insanity. It's insane >> the the juxaposition between their movements and what they're saying
00:37:41
publicly to what's going on behind closed doors with this third wheel here. After Caitlyn leaves them, Bailey and
00:37:48
Aubrey continued on their odd journey, checking into motel in Spencer and Ames, Iowa, and then they moved on to Branson,
00:37:58
Missouri. The cops seem to be about two steps behind them all the while. They're
00:38:04
trying to track a digital trail left by the two, but the two are using burner phones. So, they're speed bumps for the
00:38:12
police that are behind them and on their trail. >> Well, I have a question. So, when
00:38:16
Caitlyn gets dropped off, is she talking to police at this point or is she just too scared? Because I mean, like like
00:38:24
you said, they said you're going to help kill this exchange student and if you don't, we're going to harm your family.
00:38:31
So, I wonder when they dropped her off, did they say, "You better keep your mouth shut or we're going to harm your
00:38:37
family?" >> That's a great question. I don't know. We know that Caitlyn communicated
00:38:42
everything or we believe everything >> to law enforcement. >> Yeah. To her knowledge about these two
00:38:47
to law enforcement. We just don't we don't know when that happened, right? >> Place. And if they're moving city to
00:38:56
city then state to state, it it still leaves them leaves law enforcement behind. But see, the FBI, they're able
00:39:04
to use that Facebook live stream video to hone in on the digital source because they're using these phones, but the the
00:39:15
Facebook live stream video, they they used a phone registered to Bailey Boswell. That phone had called a number
00:39:22
at the Windmill Inn in Branson, Missouri. Naturally, you're going to go there hoping to either A find this
00:39:30
couple there or B sitting there waiting for them when they arrive. And that is where the two of these the
00:39:38
two will be arrested on November 30th. So, they're nabbed on federal persons of interest warrants as well as charges
00:39:46
unrelated to Sydney Lof's case. completely. So, Aubrey was wanted for possession of a firearm by a felon.
00:39:55
Bailey was wanted on failure to appear on a minor drug charge in Lincoln, Nebraska. When the two were arrested,
00:40:03
found in their possession were maps, hiking and camping gear, a supply of bottled water, sleeping bags, and so on.
00:40:11
Every indication is that they were on their way to Mexico. Bailey and Aubrey agreed to speak with police
00:40:17
investigating Cydney's case. The short of it is they're going to stick to their story that was on the live stream video,
00:40:24
right? >> That Sydney was last seen by them alive and well in Wilbur. Bailey had dropped
00:40:31
her off at someone's house and went about her life. She had no idea what happened to Sydney. Neither did Aubrey.
00:40:40
You know, at the top of the show, we were giving out some toast. I should probably mention here the shout out that
00:40:46
is in order. We we could not have written this episode without the incredible reporting by the Grand Island
00:40:53
Independent in cooperation with the Lincoln Journal Star and the Omaha World Herald, all on omaha.com's
00:41:02
website. Using phone tracking information from two of Baileyy's cell phone accounts and a flip phone
00:41:09
registered to Aubrey, Lincoln police detective Bob Hurley and the FBI track the movements made by the phones on
00:41:18
Wednesday, November 15th and Thursday, November 16th. So keep in mind this is this is at the time when Sydney is first
00:41:27
missing, >> right? This is 14 to 15 days before the two who are seemingly on the run are apprehended
00:41:37
in another state. They looked at the pings and considered the length of time it appeared the phone spent in different
00:41:46
locations. They started looking at a very specific location, then methodically did a foot search 25 miles
00:41:54
of remote roadways using cadaavver dogs. So Sydney's missing. Two weeks later, these two are apprehended who said they
00:42:03
had nothing to do with her, even though it appears at least Bailey may have been
00:42:08
the last person to see Sydney. But then it's on December 4th. Body parts were found in in spilling out of black trash
00:42:18
bags scattered in overgrown ditches along a gravel road outside of Edgar. This is in rural Clay County. The
00:42:28
location was an hour's drive from Wilbur and had been visited by Bailey's and Aubrey's phones
00:42:37
on November 16th. Then more remains were found the following day. The the total number of body parts recovered was 14.
00:42:45
The body was not complete. An upper arm was never located and it was Jesus. at the time. Obviously, it's not yet
00:42:54
confirmed to be Sydney, but the cops were pretty much >> Yeah. >> sure that she had been disposed of and a
00:43:02
lot of this basing a lot of this on phone locationational data. >> Yeah. I'm guessing the FBI, like you
00:43:07
said, they're able to track down these pings, look at the location, look at the time spent. the chances of them. I mean,
00:43:17
this is somewhat of a Hail Mary, but obviously there was some detective work, some Sherlock Holmes stuff going on
00:43:24
here, but then to find body pieces like like you said, it's not confirmed, but what are the chances? It's going to be
00:43:31
somebody else or just some random person. Well, that wasn't the only thing found in the ditches. Wrapped inside
00:43:37
30gallon trash bags were sex toys, a cat leash, a size seven women's boot, duct tape, tarps, a sauna suit with the
00:43:48
crotch missing, a glove, men's underwear, two socks, and a size 4XL green shirt with a bleach stain on it.
00:43:58
Also found were Sydney's slip bra and shirt. The shirt was the one she was wearing in the last Snapchat photo she
00:44:07
sent to her friend saying, "Ready for my date." The cops told the media, quote, "By their own statements on social
00:44:15
media, we believe that Aubrey Trail and Bailey Boswell were the two of the last people to see
00:44:23
Sydney before her disappearance. Thus, they remain persons of interest." End quote. Remember, they had not been
00:44:29
arrested for anything related to Sydney at this time because they had outstanding warrants, but that's going
00:44:35
to change. >> But it's good that they have these other charges because it it places these
00:44:40
suspects in holding basically. >> Yes. The autopsy told us that she had been cut into 14 pieces by at least two,
00:44:48
possibly three different instruments. The doctor, a forensic pathologist said there were indications of a struggle
00:44:55
before death with deep bruises on the back of her head, down the middle of her back, and on her inner thigh. She had
00:45:04
been restrained at the wrist and had freshly torn a freshly torn earlobe at the piercing site. As for the cause of
00:45:13
death, Sydney's hyoid bone had been crushed. Other evidence concluded that she had been strangled. Sydney's body
00:45:20
also showed indications that around the time of death, she experienced blunt force trauma. The autopsy was
00:45:28
complicated by the absence of most of the organs of Sydney's torso and abdomen, as well as the absence of other
00:45:37
body parts such as the upper part of the trachea, windpipe, linex, and veins and
00:45:42
arteries of the neck. These appear to have been removed postmortem by the use of a sharp blade. None of these items
00:45:52
were ever found. Well, the thing about this ruse we're going to get on a dating website were a couple. They're
00:45:59
essentially looking for a female, but they this female doesn't have to be willing. But hey, I go on this date. I
00:46:08
try to present myself as best I as I can to the version of the person I'm telling
00:46:13
you I am online >> that will drop your guard a little bit trust. Hey, you don't need to drive.
00:46:21
I'll come pick you up. And we don't know if they drugged to her when she got in the car. Hey, I got I picked up a drink
00:46:29
for you at the gas station. Here you go. And all of this was just a ruse to find
00:46:37
a victim. >> Well, and yes, let's talk about what we do know happened because there is a
00:46:42
digital paper trail here, >> right? >> So, Sydney met this Audrey on Tinder on November 11th. They exchanged
00:46:52
140 plus messages on the dating app in which Sydney relayed that her family lived two hours away, that she lived
00:47:00
alone, and she worked at Menard's in Lincoln. It was evident she was lonely and alone. On Bailey's half of the
00:47:08
conversation, posing as this Audrey, no mention was ever made of a male in Audrey's life. The two arranged for this
00:47:16
first date on Tuesday the 14th. So Cydney gave Audrey her home address and within moments Bailey had searched the
00:47:25
location and found a hotel. On the 14th, Bailey and Aubrey, her bow, checked into
00:47:33
that motel or that hotel. Bailey picked Sydney up and they drove around and smoked some pot and they
00:47:40
>> Yeah, they smoked some pot and then she dropped her off back at home. >> Aubrey never made an appearance on this
00:47:46
date. Now, after the date, Bailey met Aubrey at the hotel. They spent the night together. Then, the two women
00:47:54
agreed to meet up the next evening after that first date. On the morning of Bailey's second date with Sydney, so
00:48:04
remember this is November 15th. Bailey and Aubrey went to a Lincoln Home Depot. They're captured on video. There's no
00:48:13
disputing this. and purchased tin snips, hacksaws, and tarps. Then they went to the Menards where Sydney worked. She's
00:48:22
actually working at this time. It's unclear if this was so Aubrey could check Sydney out, but what we figured
00:48:30
out is there's no sign that Bailey ever went inside, but there's security video from Menard's showing Aubrey walking
00:48:38
past Sydney in the other direction as she walked outside. She was going to do a shift at the lumber yard shack. So the
00:48:47
video captures this Aubrey walking past the victim. >> Yeah. Almost stalking their prey.
00:48:55
>> Yeah. And so right after the victim passes him, he turns around and looks at her, maybe does a double take, and then
00:49:04
he makes a call on his cell phone. We now know that that call went to Bailey Boswell. So, after stalking Sydney at
00:49:13
the Menards, Aubrey went to a hardware store and bought chemical drain cleaner and an extension cord. Meanwhile, Bailey
00:49:22
purchased bleach, trash bags, duct tape, and roasting pans. Throughout the day, Bailey texted Sydney to ask how her day
00:49:32
was going and to communicate that she was looking forward to their date. Later that day, after Sydney got off work and
00:49:41
got home, Bailey messaged Sydney at 6:54 saying, quote, "I'm outside." So, she picked Sydney up and brought her to the
00:49:51
Wilbur apartment. Aubrey was, we're guessing, waiting inside this apartment. Some of this can be sorted
00:50:01
out through cell phone records, >> right? Sydney's phone shut off at 8:32 p.m. They're communicating at 6:54.
00:50:10
Let's call it 7:00 p.m. They make they drive this distance. It's a considerable distance to get to the apartment in in
00:50:17
another city in in Wilbur in the town of Wilbur. Sydney's phone shuts off at 3 at
00:50:24
8:32 after pinging in Wilbur at that location at 8:30. >> Yeah, this is a setup. And there would
00:50:33
be no way of Sydney knowing. We have to speculate because we don't know. Like I said, did
00:50:40
did did they give Sydney a drink to incapacitate her before she got back to this uh basement apartment? Or was it
00:50:50
just a complete ambush once they got her back? Because she wouldn't have known what she was walking into or who she was
00:50:58
going to walk into. Well, if if the pings and the cell phone information is accurate to the second is it's 2 minutes
00:51:08
from arriving at that location to the phone being turned off. And I can't believe that the victim walks into a
00:51:14
place and goes, "You know what? I'll turn off my phone while I'm here." I I think that the that the trauma to her
00:51:21
back and head are, like you said, probably an ambush takes place and the phone goes off right away. And it wasn't
00:51:28
Sydney that turned it off. Now, as far as torture or whatever that that followed, we don't know anything about
00:51:34
that, but based on what we have learned since about the proclivities of these two, we can sort out that that's
00:51:43
probably part of it. The bruises and the restraint marks on Sydney's body spoke for themselves. Then, one or two, one of
00:51:52
the two, Bailey or Aubrey, held Sydney down while the other strangled her with an extension cord.
00:51:58
Then they drove the parts 60 miles away to Klay County using Aubrey's Ford 500 sedan. Cell phone records placed them in
00:52:10
remote Klay County on the afternoon of November 16th, leaving the parts and trash bags behind when they leave. Back
00:52:18
at the apartment, 621 West 7th Street, Bailey and Aubrey went crazy with the bleach. They even wiped down the walls
00:52:27
with it. They use so much bleach to clean up the basement that the owner remember so the owners are living above.
00:52:34
>> Right. That's my question is they're in the basement apartment. We don't have
00:52:39
any eyeball witnesses or earball witnesses. >> Well, you can access the basement. You
00:52:46
don't have to go through the main home. >> It's essentially a a like a duplex. >> But what I'm wondering is like do they
00:52:54
do they hear somebody scream? Do they hear any commotion? Do they hear anything?
00:53:03
>> We don't have statements from them indicating that they heard anything or saw anything that was suspicious.
00:53:09
>> They might not have even been home at the time. While they were at home for part of this
00:53:15
because before the couple goes on the run between the killing and going on the run, they they wipe down the entire
00:53:22
basement with bleach. And the the smell is so bad that the act that the wife actually had a physical reaction. She
00:53:29
got sick from the amount of bleach that was used. And the odor of that will can cause people to to get sick,
00:53:38
>> right? And when news of Sydney's disappearance made headlines, made news, and these two
00:53:46
are named persons of interest, they left town. So much more to get to. Join us back
00:54:00
here in the garage. Same bat time, same bat channel. Until then, >> be good, be kind, and don't litter.
00:54:07
Heat. [Applause] Heat.

Badges

This episode stands out for the following:

  • 90
    Most heartbreaking
  • 85
    Most shocking
  • 85
    Biggest twist
  • 80
    Most intense

Episode Highlights

  • Aubrey's Confession
    Aubrey Trail admits to being a lifelong criminal but denies murder.
    “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.”
    @ 30m 53s
    August 19, 2025
  • Bailey's Apology
    Bailey Boswell expresses her sorrow for Sydney's family during a live stream.
    “I just want the family to know I am truly sorry.”
    @ 32m 54s
    August 19, 2025
  • The Last Date
    Sydney's last known communication was a Snapchat saying she was 'Ready for my date.'
    “Ready for my date.”
    @ 44m 07s
    August 19, 2025
  • The Tinder Connection
    Sydney and Audrey connected on Tinder, leading to a series of messages and a first date.
    @ 46m 45s
    August 19, 2025
  • The First Date
    Sydney and Bailey, posing as Audrey, met for a date, but Aubrey never showed up.
    @ 47m 43s
    August 19, 2025
  • A Chilling Setup
    Bailey and Aubrey prepared for their second meeting with Sydney, purchasing suspicious items.
    @ 48m 11s
    August 19, 2025
  • The Disappearance
    Sydney's phone shut off shortly after arriving at the apartment, indicating a possible ambush.
    @ 50m 01s
    August 19, 2025
  • The Aftermath
    Bailey and Aubrey attempted to clean up the crime scene with excessive bleach.
    @ 52m 21s
    August 19, 2025
  • Leaving Town
    After Sydney's disappearance made headlines, Bailey and Aubrey fled the area.
    @ 53m 42s
    August 19, 2025

Episode Quotes

  • Ready for my date.
    Sydney Loofe /// Part 1 /// 864
  • I just want the family to know I am truly sorry.
    Sydney Loofe /// Part 1 /// 864
  • Yeah. Almost stalking their prey.
    Sydney Loofe /// Part 1 /// 864
  • I'm outside.
    Sydney Loofe /// Part 1 /// 864
  • This is a setup. And there would be no way of Sydney knowing.
    Sydney Loofe /// Part 1 /// 864

Key Moments

  • Back to School24:24
  • Online Learning24:38
  • Missing Persons28:24
  • Body Parts Found42:14
  • First Date Setup47:14
  • Phone Shutdown50:24
  • Crime Scene Cleanup52:24
  • Fleeing the Scene53:48

Words per Minute Over Time

Vibes Breakdown