Dane Cook has had a long and exciting career as a comedian. He’s sparked plenty of laughs but also some controversy. 

Dane Cook dominated the comedy scene in the mid-2000s, earning millions of dollars. After recruiting his half-brother, Darryl McCauley, to work as his business manager, he was revealed that he couldn’t be trusted. 

Between 2004 and 2008, McCauley and his wife managed to embezzle tens of millions from Dane. From forging checks, opening up businesses, and purchasing properties, Darryl McCauley screwed Dane Cook over. 

Darryl McCauley Was His Business Manager

Dane Cook reigned throughout the 90s and early 2000s, earning gigs across the globe, landing special after particular, and even going as far as selling out Madison Square Garden. It was evident that Dane was doing very well for himself, despite it taking a bit of time to reach that level of fame and success.

From the 1990s to 2008, Dane Cook’s half-brother was his business manager. Darryl McCauley made a staggering $12,500 per month while working in the role, and as fans on Reddit discussed, that should have been enough to carry him through life well enough.

 At least, that’s what the average office worker would assume. Later, it turned out that Darryl had a side gig he wasn’t about to reveal to anyone but his wife (though she’d pay the price, too).

Dane Cook found out Darryl McCauley was stealing from him when he moved to California.

Dane Cook found out his brother had been stealing from him for years while purchasing a house in California, he said on the “Your Mom’s House” podcast in 2019. Darryl McCauley had been Cook’s manager for a long time. 

Still, Cook needed to replace him when he relocated to California for tax purposes since his company was operating out of a PO box in Massachusetts. “Once you’re a resident, you can’t do that. The IRS doesn’t, you know, because it’s less taxes in Massachussetts and all that stuff,” he explained. 

So Cook called up his brother and told him that his business would have to move with him. Cook said he intended to keep McCauley in the company but in a different role. “He did not like that because he had been sending me fake statements for maybe 10 years,” Cook said. That’s right. McCauley had deceived his brother for a whole decade. 

Cook found out on a Monday morning when his new business manager noticed discrepancies. The previous Friday, Cook wrote a letter to his brother to ensure him that things would work out and shared some of the ideas he had for this next chapter, Cook told the podcast hosts. McCauley responded and closed his letter with “To the future,” Cook detailed. “I loved my brother. I really did. He was my first real best friend in my life,” Cook said. 

How Much Money Did Darryl McCauley Take?

Dane Cook’s half-brother Darryl embezzled millions of dollars from Dane’s accounts, but hardly anyone wanted to specify an exact amount. Since the crimes occurred between the ’90s and ’00s, though, the amounts weren’t astronomical by today’s standards.

It was a lot of cash, though; Darryl was charged with 27 counts of “larceny over $250” plus various embezzlement and forgery. One specific amount was $3M in forged checks. The total didn’t come out until the terms of Darryl’s trial were publicized.

Dane Cook’s brother was ordered to repay his sibling $12 million when everything was said and done.

Where Is Darryl McCauley Now?

In 2010, Darryl McCauley was sentenced to “five to six” years in state prison. After his release, he was also slated for ten years of probation. Looking at the dates, Darryl should have been released from prison around 2015 or 2016 and remained on probation until at least 2025.

As for the pair’s relationship today, Redditors point to interviews Dane’s given on the subject. When asked about the events due to Darryl’s betrayal, Dane says he “loved” his brother. As in, past tense.

And fans can agree that having your half-brother steal millions out from under your nose while working for you, day after day and year after year, had to have been rough. It’s not surprising there’s no family tie there anymore!