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True crime. Casually done.

A $9 Million Murder: Alaska’s Teen Hitman Tragedy

The internet is a dark place. One minute you’re watching videos of cats wearing funny little pyjamas, and the next, the YouTube algorithm has pushed you towards some Englishman gleefully recount the details of horrific murders from around the globe. Truly grotesque stuff. It’s little wonder that parents are so worried about what their kids get up to online.

And after today’s story, you’ll probably agree that their fears are well-founded. In today’s CasCrim short, we’re going deep into a murder plot that began on the dark side of the web; the story of how one group of everyday Alaskan teens was manipulated by a twisted and depraved online creep into committing the worst crimes imaginable. 

In the summer of 2019, what began as a tragic disappearance spiralled out into a complex murder-for-hire plot, featuring a young romance, a $9 million dollar pirze, and the callous execution of an innocent young woman. Consider this a PSA: don’t believe everything you hear online (and more importantly, if an internet stranger ever asks you to kill someone, probably better give it a pass).

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Young Hearts, Run Free

Today’s tragedy actually begins, unexpectedly, as a romance. In the early months of 2019, Anchorage teen Denali Brehmer met the man of her dreams: a handsome, charming, 21-year-old multi-millionaire named Tyler. Straight away she was head over heels in love, but there was just one problem. She had never actually met Tyler as such, because while she was trapped up in the desolate northern wastes they call Alaska, he was all the way down in the desolate midwestern wasteland they call Kansas.

Their relationship took place entirely virtually, a whirlwind romance conducted mostly through the medium of Snapchat (for those of you not familiar, a few years back this was the app of choice for those looking to exchange pictures of their genitals). For Denali, the distance was just a minor road bump in her fairytale love story. What mattered most  was that in Tyler she’d found a confidante who could listen to her troubled past without judgement.

She had suffered quite a troubled upbringing. At a young age, she and her half sister were taken from their mother after allegations of abuse, and handed over to state care. Denali changed her name after being adopted, and started a habit of hiding behind a string of fake monikers — Dakota, Angela, Angel. It was that last one she went by online.  

Tyler didn’t care about any of that. He didn’t even care that ‘Angel’, despite being just 18, had a daughter of her own who was also given up for adoption. That’s part of any healthy relationship after all: accepting each other’s flaws and history without shame.However, when her new love started to share some of his own dark secrets, her fairytale romance took a bit of a turn. See, this Prince Charming turned out to have some… unsavoury predilections (to put it lightly). 

It began shortly after they got together. Tyler started to gradually introduce his twisted sexual desires into their conversations whenevr possible, hinting that he wanted Denali’s help to live out his fantasies. And I’m not talking about a bit of harmless role-play here — this guy wanted the real deal. 

Several months into their relationship, it all came to a head when he texted Denali with a proposition that would change her life forever: he was willing to make her rich beyond her wildest dreams…. All she had to do for him was kill someone…

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The Teenage Death Squad

Now in my limited experience, when your Tinder convo veers towards a murder-for-hire plot, that’s usually the time to un-match. However, Denali Brehmer didn’t share my canny intuitions. Perhaps she was blinded by love… Or more likely, blinded by the nine million dollar fee she was promised. 

Yep, her wealthy older boyfriend was offering up a nine-figure bounty. All she had to do was take someone’s life (it could be anyone), and provide video documentation as proof. I know at least a couple of our listeners just thought to themselves: “Nine million? I’d do it for nine grand!” 

If that’s you, you’re truly awful (everyone knows you should charge a $100k minimum).And  Denali’s moral compass was about as skewed as yours, because she didn’t balk at the offer. According to text conversations found on their phones, she readily accepted, and the next few days were spent hammering out the details of Tyler’s indecent proposal.

This is where things got a bit tricky. See, most of you listening are probably pretty well-versed in the ins and outs of the criminal arts. You’re the sort of people that — even though you’re absolutely lovely and would never hurt a fly — most likely know 10 different ways to effectively dispose of a body without leaving a trace of evidence behind. It’s just a side effect of listening to thousands of hours of murder stories.

It can be easy to forget that this is by no means normal information to possess (seriously, nobody but the coroner should know as much about the decomposition process, you sick bastards). Denali was not a student of True Crime University, so she was as clueless as your average, well-adjusted person when it came to the intricacies of death and destruction. 

If she was going to pull it off, she would need some help. So in May of 2019, Denali got to work scouring the criminal underworld of Alaska, enlisting the help of some of the toughest gangsters and contract killers she could find and—… 

Hold on no, that’s not right. According to my notes, what she actually did was just ask her mates… the same mates she used to skip school with to go smoke weed in the woods. Minor spoiler warning: any plan undertaken by a bunch of pubescent stoners is pretty much doomed from the start. 

Kayden McIntosh

The first to join Denali’s ragtag band of Teen Hitmen™ was 16-year-old triggerman Kayden McIntosh. This baby-faced killer was homeless at the time, so the promise of a seven-figure share of the loot was too good to turn down: one little murder, and some wealthy benefactor would set him up for the rest of his life. He didn’t even need to bring his own gun, because Denali already owned a pistol for him to use.

Similarly, the ringleader’s next recruit, 19-year-old Caleb Leyland, was all too happy to take them up on their offer: $500,000, and all he had to do was lend them his truck for the day.. Now she had a the murder weapon, a vehicle, and some poor mug to pull the trigger for her. The plan was almost good to go. 

But apparently our heroine had never heard of the expression “too many cooks/assassins spoil the broth/murder,” because she then added another 2 accomplices into the mix to help with planning. We don’t know their names or exact roles, because they were minors at the time, and therefore their identities are protected by Canadian law.

In the end, it was a full 5-man squad of would-be killers, and none of them were even old enough to legally drink. Yet now they were tasked with ending a human life. And I’m a little worried with how game they were to give it a go. Do they not have video games in Alaska? Community centres? Literally anything to keep teens occupied so they don’t go all Lord of the Flies like this? 

Apparently not, because Denali was able to muster up her gang in under a fortnight. She convened a meeting of this pimply death squad in late May to finalise the plan, promising each of them huge amounts of cash for their service and silence. The only thing left was to pick a date for the crime. 

It was decided that on June 2nd, they would put their plan into motion, and someone very close to one of them would meet a horrific end…

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A Body on the Banks

On the 3rd of June 2019, handyman Timothy Hoffman drove his motorbike down to an Anchorage police station to file a missing person report for his daughter, Cynthia ‘CeeCee’ Hoffman. The previous day 19-year-old CeeCee had gone out on a hiking trip with some old school friends, but failed to return home at night.

That might sound normal enough for an older teenager, but not for CeeCee. Mr Hoffman was especially worried because his daughter was developmentally disabled. She wasn’t yet equipped to stay out alone at night. CecCee had graduated from the special-ed programme at her high school, and at 19 she had a mental age closer to that of a 12-year-old.  

At the time of her disappearance, she was studying in a life skills school so she could one day be self-sufficient, while working as her handyman father’s assistant on the weekends. That evening, she was due to go to her father’s place to collect some money from a job. When she failed to turn up, Mr Hoffman tried ringing her, with no luck. He later told a courtroom:

“In this family, you all have phones. When dad calls, you answer. I don’t care if you’re at church and the holy pastor is preaching. I don’t care if you’re at school taking the high school diploma test. If dad calls, you answer.”

CeeCee usually checked in with him every 3 hours when she was out, but now there was total radio silence. The last anyone had heard of her whereabouts was a text from her hiking buddy, Angela. She and a young boy had picked CeeCee up to visit a national park north of Anchorage, and claimed that they had dropped her off at a playpark on the outskirts of town later that afternoon, at her request. 

Cynthia Hoffman
Cynthia Hoffman

“I hope she comes home safely she’s my best friend,” the girl added. But of course, ‘Angela’ was well aware that CeeCee wouldn’t be coming home safe. This was just another pseudonym of Denali Brehmer, and she knew exactly what had happened to Cynthia Hoffman. After reporting the disappearance to the police, Mr Hoffman started scouring the town by himself:

“I put out search parties. I drove my motorcycle through woods and bike paths. I floored it all over town doing speed limits I should not have been doing, looking for my kid.”

But it was all in vain. The following afternoon, he received a knock at the door. He knew instantly what it meant: CeeCee’s body had been found. Late that morning, she was spotted washed up on the banks of the Eklunta River, about 30 miles northeast of the city.

Her feet were duct-taped together. There was a single bullet hole in the back of her head…

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A Dubious Alibi

Now, I think we can all agree that this little criminal case study doesn’t exactly belong in the police detective training programme. It’s the true crime equivalent of a 4-piece jigsaw puzzle. Let’s take a second to approach it from the perspective of a cop. 

You’ve got a dead body. You’ve got two teenagers who were last seen with said body before said death. This pair’s alibi is that they did go into the forest with the victim, but claim they dropped her off safely afterwards (something which nobody could verify). To add to the intrigue, one of these teens is a registered firearm owner for a 9mm pistol (the same kind most likely used in the killing). 

Natural born killers, they were not. In fact, it’s quite amazing that it took five minds together to come up with this crime of the century  (even if they were teen stoner minds). Our Teen Hitmen had discovered that murder really wasn’t their strong suit. Especially when Denali and Kayden were brought in by the police for questioning on June 6th, two days after the body was found.

If you thought they were bad at murder, they were even worse in the interrogation room; their haphazard alibi crumbled faster than a shanty town in a hurricane. It was Denali who folded first, willing to throw her right-hand-man under the bus if it meant getting off lightly herself. The story she told the cops went like this:

According to Denali Brehmer, June 2nd started off like any other Sunday. She, Kayden, and CeeCee met up in the morning, planning to spend the afternoon driving around Anchorage and smoking weed. When that got dull after a few hours, they decided to head up north to visit Thunderbird Falls trail — a mile-long path through the woods which leads to the 200-foot waterfall in the name. On the way, Denali had a completely reasonable and bright idea: 

“Hey guys, you know what would be fun? Let’s wrap each other up in duct tape and take pictures in the forest. Because that’s a totally normal thing which we, as teens, would do.”

Again, apparently Alaska doesn’t offer much to keep the young’uns busy, because the other two were up for the idea of a staged kidnapping photoshoot. So they grabbed a conventionally-placed roll of duct tape and Denali’s 9mm pistol from the glovebox of the truck, and set off into the woods. 

Halfway along the Thunderbird Falls path, they took a detour onto a less trafficked trail which ran along the banks of the Eklunta River. About a mile down the new route, they came across a clearing in the trees, and stopped.  

Denali claimed that CeeCee was the first to be willingly tied up. They started with her feet, then her hands, then her mouth. Denali then posed with her gun pointed at the girl, because I guess that’s supposed to be edgy and cool. (Parents, please educate your kids on the dangers of photoshoots with live ammunition.)

It was at that point that CeeCee started to panic. She apparently forgot that it was all make-believe, and started to struggle for real. Denali pulled the tape off of the girl’s mouth and hands, but she wouldn’t calm down. She started shouting about calling the police, and reporting that the other two kidnapped and sexually assaulted her. 

The panicking girl reached for the phone in her pocket, and in response, 16-year-old Kayden McIntosh grabbed Denali’s 9mm pistol from her hand, and shot CeeCee in the back of the head. Just like that, it was over. The victim lay twitching on the ground. 

Denali was in shock at Kayden — he had just executed her best friend right in front of her for virtually no reason. A fact which McIntosh never denied. When presented with this version of events, he told the police that he ‘blacked out’ at the time, but had memories of pulling the trigger,  then dragging the helpless victim to the riverside and pushing her in while she was still moving.

Of course, this meant that McIntosh was arrested on the spot. Denali, on the other hand, painted herself as a shocked and appalled bystander. She was allowed to walk out of the police station and get on with her life…

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The Fantasy and the Fraud

If the story ended there, then Denali and the mystery man Tyler would have walked free, leaving a homeless 16-year-old to take the entirety of the blame. That wouldn’t sit very well with me, but thankfully we’re not quite done yet: the rickety house of cards built by our two inept masterminds had only just begun to teeter. It was what came next that would bring it all crashing down on top of them.

See, up until this point Denali had been living in a fantasy land. It’s one thing discussing murder fantasies with your little online boyfriend, but actually turning them into reality is another thing altogether. The reality of becoming a murderer had hit Denali like a freight train. 

Still though, the promise of a $9 million dollar payday probably does a lot to cushion the blow, right?  That would be more than enough to get her and her online lover Tyler a couple of fake passports and a new life in the Bahamas. So she pushed him on it — how about a little advance to deal with the shit she’d gotten herself into.

Well, about that… Did anyone else think that $9 million sounded a bit too good to be true? If so, you have better instincts than this Alaskan teen-mum assassin (which isn’t saying much). Most of us know not to believe everything that people tell you on the internet, but Denali wasn’t quite so canny. 

Rather than pay up on his promise, Tyler started planning yet another murder for his assassin girlfriend. And as the days wore on, it became increasingly clear that he had no intention of paying up on the first one. At this point the penny finally dropped for poor dim Denali: her Romeo was more ‘Nigerian Prince’ than ‘Prince Charming’. 

There was no nine million dollars. In fact, it was unlikely that Tyler even had nine hundred in his bank account: rather than a millionaire businessman, he was actually just a common basement-dwelling, Hot Pocket-munching, plastic-bottle-pissing internet troll. Our poor heroine had been well and truly catfished. 

It was even worse than that though. Now Tyler had her completely cornered the teenager, and there was nothing she could do to escape him. He had information which could send Denali to prison for life, meaning he didn’t need the millionaire ruse to manipulate her anymore. His messages took on a more threatening tone:

“[W]e can meet but once I see a cop I’m telling him or her that I made you rape people and killed cece.” 

Denali was forced to keep up her end of the twisted bargain despite receiving nothing in return. This finally pushed her past breaking point. Several days after the first police interview, she posted a public video to Snapchat, in which she publicly admitted her guilt:

“I just want to thank everyone that’s been there for me my whole life and these past few years and everything. I fucked up, I know I did, if I could take back what I’ve done, I can’t. I’m sorry everybody, my family, my friends. I guess you will hear from me when you hear from me, but I won’t be back for a long time. I’m sorry, I didn’t mean to do it. I didn’t mean to do it.”

But you did mean to do it Denali. In fact, the premeditation here is clearer than in almost every other case we’ve covered (and the truth of the matter would soon come spilling out). When the cops came to pick her up for a second time, Denali was forced to fill them in on everything she left out the last time. Specifically, the fact that she was to blame for putting everything in motion. She of course also told them about Tyler from Kansas, and the nine million dollar deal that wasn’t to be. 

As for the real story of what happened up by the Eklutna River, it was much the same as the first version. Bar the fact that CeeCee was actually forcibly bound by the pair, and that Denali was a much more active participant than she let on at first. Yes, baby-faced McIntosh was always supposed to be the trigger man, but rather than a hapless bystander, Denali was actually the camerawoman! 

Because as you’ll remember, part of her boyfriend’s terms were that he wanted photographic evidence of the crime as it unfolded. So while McIntosh was binding and gagging the victim, she was sending Snapchat videos to Tyler that documented every second. 

She filmed as CeeCee cried out for help. She kept filming as McIntosh put the gun to the back of her head and pulled the trigger. She even kept filming and photographing after that single shot rang out through the forest, and her friend lay dying on the floor. That’s by far one of the coldest, cruelest things I’ve ever come across writing for this show.

After the deed was done, she and the gunman travelled back down to Anchorage, where she sent the decoy text to the victim’s father. Then they called on their other accomplices to help burn Cynthia Hoffman’s ID, some of her clothing, her purse, and the gun used to kill her. Those kids who helped burn the evidence were picked up on the 10th of June, alongside Caleb Leyland (the owner of the truck). 

Diabolical Denali decided that, if she was going down, she was taking the lot of them with her. It was game over for our wannabe teen assassin, and her entire team. Denali was still penniless, utterly humiliated, and outed as a sadistic killer willing to prey on her mentally disabled best friend — the fantasy life she had been living lay in tatters. But what about the other half of that life?

The true mastermind of this whole affair was still thousands of miles away, and nobody even knew his real name…

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To Catch a Predator

How does one go about tracking down such a criminal mastermind? As I said, we don’t have a name, and once she saw through his ruse, Denali wondered if she even knew what this ‘Tyler’ really looked like. Had he covered his digital tracks properly, there’s every chance that he might have been able to cut off contact and slip away entirely.

However, this ‘Tyler’ — much like everyone else involved in the crime — wasn’t the sharpest tool in the box. Throughout their relationship, he had been using a phone number tied to his real name and address! Seriously, it’s like nobody involved had even watched a single episode of a cop show. 

The police searched through Denali’s phone, and found the mystery man listed under the name ‘Babe’. A quick search of the phone records revealed that Babe, aka Tyler of Kansas, was actually Darin Schilmiller of Indiana. Court documents note that: “He does not look like the young man he portrayed himself to look like, he is not a millionaire and he lives in Indiana,”

So what does he actually look like? Hmm, how can I put this nicely? Not the sort of looks you’d kill for. Or to put it less nicely: he roughly resembles a human-shaped lump of grime scraped off of 4chan’s floor. I’m not just being mean here — from the sounds of it, Schilmiller sounds like one of the worst cretins that the internet has to offer.

The media descended on his tiny hometown when the news broke, harassing bemused family members, and any local that would talk to them for information on the enigmatic Schilmiller. The reports they gathered from his acquaintances sound… about as bad as you’d expect for a guy who fantasises about making women kill people for his pleasure. An old schoolmate told local Indiana media that he had a habit of making fake social media profiles to try to coerce pictures from younger classmates. When his peers grew up, he began asking for pictures of their children instead… The woman added:

“I think most people just thought it was because he didn’t know… like he was just slow. He knew the difference between right and wrong. He didn’t steal. He really didn’t do anything bad. I guess he just didn’t understand life.”

Oh yeah! He didn’t do anything bad — he just asked single mothers to provide him with images of their children’s soiled diapers. It’s not like he was some kind of dirty shoplifter or anything (God forbid!). Rather than bang our heads against the wall trying to figure out where that woman draws the line on morality, we’ll just say that it was basically an open secret that Schilmiller was messed up.

The small town of New Salisbury where he lived had a population of just 600, and pretty much all of them knew that he was a legendary creep (he was even investigated by the FBI in 2018). So it came as little surprise when, several days after his involvement was made public, Schilmiller and his teenaged girlfriend were hit with a slew of extra charges concerning some terrible happenings in the days after the murder. Apparently Schilmiller went a bit mad with power, and attempted to force Denali into as many depraved acts as possible before the game was up.

After the murder, both of them had deleted their text records, but the cops subpoenaed Verizon to get a copy of their logs, and forensic technicians were still able to recover mountains of data from the devices. Among this data were messages and images relating to two more crimes in the days directly after the killing. 

Schilmiller had used his new leverage to force Denali into committing a pair of sexual assaults for his sick amusement — both with underaged victims. Among the text messages listed in the court documents are gems like: “Gonna go buy weed first. I wanna get her high for it so she doesn’t fight me.”

There are other quotes from these text messages which I found in news reports, but it’s been days now and I can’t burn the words from my corneas. I’ll spare you all that particular bit of unpleasantness. With her back against the wall and nowhere to turn, Denali found herself at the mercy of this sexually depraved neck beard, which is probably why she just chose to turn herself in before their crime spree went any further. 

Not that I feel particularly sorry for our little teenage executioner — I mean, technically she was a victim in a sense, but remember she only agreed to the murder in the first place in the hopes of getting a fat paycheque from the fictional millionaire. Her motivations were purely selfish, and she had months (not days, not weeks) to turn over the implications in her mind. Yet still she chose to go through with it.  

Now she and her boyfriend were going to pay the price. For his role in orchestrating the crime, the FBI promptly swooped in to pluck Tyler/Schilmiller out of his grandmother’s basement (I’m not joking, that was actually his living arrangement at the time). His bail was set at $1 million, and the Alaskan prosecutors immediately began the extradition procedures to bring him up north. 

Finally, the doting couple would be able to meet in person! Although, probably not under the circumstances either of them were hoping for…

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As Things Stand

If there’s one positive we can glean from this story, it’s that the whole plot was so haphazard that every single person involved is incriminated beyond belief. That made for a relatively swift and efficient investigation. However, the same can’t be said for the legal proceedings. 

From his jail cell in Indiana, Schilmiller openly confessed to masterminding the crime, and even admitted it was he who chose CeCe as the victim. He, Denali Brehmer, Darin Schilmiller, Caleb Leyland, and Kayden McIntosh were indicted on first and second degree murder charges, as well as multiple counts of conspiracy to commit murder. 

Despite being just 16 and having the appearance of a 12-year-old (rocking baby’s first moustache), McIntosh is being tried as an adult (seeing as he was the one who fired the fatal shot). The two unnamed juveniles were served similar charged related to their part in plotting and covering up the murder, but since the court never ruled to try them as adult, their identities will be portected for life. 

Everyone involved is looking at a maximum 99-year sentence if found guilty on those first-degree charges, which CeCe’s father thinks isn’t enough. At a vigil to remember his daughter, he told the media: “I have one thing on my mind, and that’s to send all six of them to hell. And I ain’t gonna rest until it’s done.”

Since Alaska doesn’t have the death penalty, he’ll probably just have to settle for life behind bars (which is looking incredibly likely for at least the three main culprits). Brehmer and Schilmiller both face a slew of additional charges related to the images of the sexual assaults found on their phones, which could take a few more decades on top for good measure.

 As things currently stand, everyone involved has pleaded not guilty. If I had to take a wild guess, I’d say that they’re all hoping to shift responsibility up the chain of command and claim some lighter charges for themselves. Unfortunately, it’ll be a while before we know how that pans out. 

This is pretty much where the story ends for now. The trial has been subject to a series of delays on account of the massive piles of evidence which these halfwitted hitmen left behind. Seriously, the defence team have had to request two delays just to pick through the hundreds of thousands of pages of evidence stacked against them. Consider that a bit of a spoiler alert for how this will eventually end.

Although it’s a long and arduous process, CeeCee’s father Timothy Hoffman has been there every step of the way. He’s pledged to attend every single court date right up to the sentencing, as a constant reminder of the pain this gang of would-be contract killers inflicted upon his family. In an early pre-trial hearing, he stood up to tell the court:

The only thing I know is that my daughter trusted these people, my daughter just wanted friends. Now I have to bury her.”

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Wrap-up

And that’s where we’re forced to end for the day. Hopefully someday soon we’ll be able to follow up on the court proceedings, and check in with our plucky gang of teen hitmen in prison. Despite still basically being children, this lot were willing to betray the trust and end the life of a developmentally challenged girl who just wanted to be their friend. CeeCee would have continued learning how to navigate the world, and perhaps one day found friends that actually deserved her company.

Instead, she fell victim to a group of cld, calculating schemers who valued their own (idiotic) shot at wealth above her life. It’s tough to express how cold and callous that is. All it took was the promise of a bit of money, and these teens were willing to do the bidding of a twisted online pervert. I can’t even begin to unpack how messed up that is, but here’s what the US Attorney in Alaska told the press as the pre-trial hearings got underway:

“For all the good the internet can do, it can be a very dark place. Parents would be wise to monitor the activity of their children online.”

After today, I would have to agree. Probably best that all you parents out there make sure that your little angels haven’t been recruited as a personal assassin by some catfishing incel — better safe than sorry. And for any young ones listening in, I’m begging you: if an online creep ever asks you to commit a crime for money, please, do the right thing… 

Demand to see half the cash up front, with the rest provided after the job. Don’t be like these idiots — it’s just basic business sense.

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Appendices

1. The latest update I can find on the case is from June 2021, when father of the victim Timothy Hoffman held a memorial ride with the Alaska biker community to raise money for Victims for Justice (the non-profit that has aided and advised him throughout the ordeal). While we await news on the trial itself, it’s at least nice to know that the community up in Anchorage isn’t going to let CeeCee be forgotten anytime soon. 

2. Last of all, a word of warning to be careful out there — apparently the tech savvy psychopaths of Gen Z just can’t get enough of committing violence for online consumption. Just this September Vice reported on an epidemic of youth murders in the UK where kids will show off their knives on Snapchat, brag about straight up murdering each other, and even post the final moments of their victims to their story… I will be absolutely livid if the last thing I see on this earth is some pre-pubescent dickhead waving an iPhone in my face.

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