Ray William Johnson: True Story Podcast - How Dane Cook Lost $12 Million Dollars

Episode Date: June 17, 2025

Dane Cook’s half-brother, Darryl McCauley—who had also been serving as his business manager—admitted to embezzling millions from Cook’s company between 2004 and 2008, siphoning off funds into his personal accounts, including writing a $3 million check to himself

This is your fix. I am your host, Stasi Schroeder. Welcome to Tell Me Lies, the official podcast. What's the most unhinged thing of season three? Stephen, because he's so evil. I do think he is misunderstood. You see everyone base consequences. It's intoxicating.

The writers just know how to trick you. There's always a twist in this show. Tell Me Lies, the official podcast, January 6th, and stream the new season of Tell Me Lies, January 13, on Hulu, and Hulu on Disney Plus. Do you remember when this famous comedian got robbed for $12 million? Now, this whole story starts with this guy, Dane. And Dane's around 16 during this time, living in Boston, and his family is struggling. They're surviving on welfare and food stamps. But one day, he decides he's going to get himself and his family out of the struggle,

and he's going to do it by becoming famous in the comedy world. So over the next few years, he spends all his time trying to trying to be a comedian. Like every night he's working on his material and local comedy clubs. And by the time he's in his 20s, Dane is spending every single night working the scene trying to make this happen. And he does this for years. There's a big naked white guy, no peepee. He had no Percoc, he had nothing down there.

But then, in 1998, he finally gets a bit of a break. He gets a stand-up segment on Comedy Central. Then in 2000, he gets his own half-hour special. I wish I was a snake. Dude, you ever wish you were a snake? And of course, being on TV helps promote his live shows, so now he's making a little bit of money. And with some of this money, he wants to make sure his family is taken care of.

And so he buys his mom a nice house. But he also wants to help out this guy, Daryl. Daryl is Dane's half-brother and his very close friend. They actually grew up together. And so Dane goes to Daryl and he's like, hey, you want a job? I could pay you to be my business manager or something. And even though Daryl really doesn't have much experience with this stuff, Dane really wants to help him out.

So Daryl hears this offer and he's like, all right. And he comes on board as business manager. And Dane pays him a salary and Daryl handles a lot of Dane's finances and make sure his taxes are paid on time and stuff. So this deal works great for both of them. Then in 2002, Dane does something completely unheard of at the time. He starts taking advantage of the internet, which is. the norm now, but stand-up comics aren't doing this in 2002. But Dane is smart. He makes a website and he's like posting footage of his stand-up shows and through this he starts getting an even

bigger fan base. Then in 2004, he starts a MySpace page. Remember Myspace? One of the first really big social media platforms. Again, stand-up comics were not doing this at the time. But Dane does it. And this gives him tons of visibility and suddenly, Caboom, his career blows the fuck up. And now he's everywhere. And he has millions of followers. His comedy albums are going platinum. He's performing at Madison Square Garden, sometimes twice in one night.

And suddenly, Dane is far from being the welfare kid he started out as. Now he's one of the biggest comedians in the world. And everyone around him is super happy for him and very supportive. Until... Well, not everyone is very supportive. Darrell, his business manager, his half-brother, his longtime close friend, Daryl sees his younger brother experiencing all this success and making all these millions of dollars, and at some point he starts to think that maybe he's entitled to some of it.

And Dane already pays him $150,000 a year salary, but that's apparently not enough for Daryl. He wants more. And instead of asking his brother for a raise like a normal person, He decides he's just gonna steal it. So he gets to work and he starts wiring money from Dane's business accounts right into his own personal account and he writes fake checks from Dane to himself and Daryl is good at covering his tracks. He like sends Dane fake bank statements to make it look like all the finances are good and that everything is adding up. And as the years go by, he steals millions from Dane and his wife is helping him do it like this turd, Erica.

And Darrell and Erica are spending this stolen money. They buy jewelry, they buy an $800,000 condo in Maine, they invest in a bunch of businesses like a hotel complex and a couple of restaurants. Darrell even racks up over a million dollars in credit card debt, just buying shit for himself, and then he pays that credit card off with Dane's money. And just in case, all this goes south, he starts hiding hundreds of thousands of dollars,

in cash, in the walls at his multiple homes he now owns. In total, it's estimated that he stole a minimum, a minimum of $12 million from his own brother. And poor Dane, like, he's working so hard. He doesn't notice any of this money is missing because he believes these bank statements, and of course he trusts his brother, like they grew up together. But then Daryl's scheming all starts to fall apart. Because as Dane becomes more and more famous, he starts getting a lot more movie deals and stuff, including a movie with Kate Hudson, one with Jessica Simpson, another one with Jessica Alba.

And so in 2008, Dane officially becomes a resident of California, and he starts having his taxes filed there. And as such, he has to find a new business manager in Los Angeles, one who's a little more experienced with that side of things. And it sucks to do, but Dane has to go and break. the news to his brother, that he's switching managers. But he says that he'll figure out a new job for him, you know, keep him in the family business and help him out. Now, I assume Daryl acts all chill about this, but obviously handing over the books to someone else is horrible news for him. I mean, like, what if this new manager sees that he's been stealing all this money? And so eventually, Dane's new manager does his job and he hits up Daryl to hand over all of Dane's financial records. And Daryl

starts acting really shady and like he makes up all kinds of excuses as to why he can't do it and this stalls things for a while. However, Daryl realizes that he can't keep this up for long. He needs a new plan fast. And so in a panic, he starts Googling things like white collar attorneys and how to hide money. And when that doesn't get him anywhere, he eventually realizes that his only option is to go on the run. And so he and his wife, they start to start to be. making plans to leave and travel the world. Then he forges Dane's signature and writes one last check to himself for $3 million and he deposits it into his personal account. Meanwhile, Dane's new manager hits up Dane and is like, uh, your brother's ignoring me. And so Dane sends Daryl a stern

message saying, bro, you need to FedEx those documents right now. And Daryl's like, I'm working on it. But he's definitely not working on it. Because two days later, Daryl and Erica hop on a 4 a.m. train headed out of the state. Then they rent a car and they drive somewhere, I don't know, they completely disappear off the map. And this disappearance is when Dane gets super suspicious, as he's finally starting to realize that his brother might just be a terrible person. And so he goes to Bank of America himself because he's going to try to get into his accounts. But as it turns out, he doesn't even have... access to his own bank accounts. And when the bank managers finally do let him into his accounts,

where there should be millions of dollars waiting for him, he sees there's actually zero dollars waiting for him. Apparently, Daryl cleared these accounts all out. And of course, this is devastating for Dane. Like, how could someone so close to him betray him like this? I mean, this is probably some of the worst pain he's ever felt in his life. And so, he has no. He has no. choice but to finally go to the police. Then a few weeks later police find Daryl in Massachusetts and boom they arrest him and I don't have a mugshot for him but here he is in court in handcuffs. Also bam they arrest Erica. Here's her mugshot and Darryl pleads guilty and he gets sentenced to six years in prison while Erica she gets

three years in prison and they have to pay Dane back all the money they stole. So Good for him.