Dane Cook Offered to Waive $12 Million Embezzlement Judgment Against Brother If He Participated in New Doc. He Refused
Dane Cook Offered to Waive $12 Million Embezzlement Judgment Against Brother If He Participated in New Doc. He Refused
Lizzie HymanThu, October 1, 2026 at 12:51 PM UTC
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Darryl McCauley in court in 2009 (left) and Dane Cook on Sept. 14, 2026.Credit: Ted Fitzgerald/MediaNews Group/Boston Herald via Getty; Jenny Anderson/Getty -
Dane Cook’s half-brother Darryl McCauley stole million of dollars from the comedian and then disappeared
McCauley, who was sentenced to six years in prison, was offered a cancellation of the $12 million restitution obligation in exchange for an interview for a new documentary about Cook
Funny Money: The Dane Cook Story is now available to stream on VOD
Dane Cook is reliving his comedic rise and “his crash at the hands of the person he trusted most” after his half-brother Darryl McCauley stole millions of dollars from him and ultimately disappeared.
The new documentary Funny Money: The Dane Cook Story explores the unraveling of the close relationship between Cook, 54, and McCauley, 61, as brothers and business partners, through archival footage and interviews with family, friends and those involved in the criminal case.
“He was the greatest, the most helpful, the most loving,” Cook and McCauley’s sister Kelly Amann says of McCauley in the documentary. “He never forgot a birthday. He was like the perfect brother.”
From left: Dane Cook and Darryl McCauley with family in Boston in 2008.Credit: MediaNews Group/Boston Herald via Getty
A former corrections officer, McCauley “was so happy he could be part of Dane’s success” after Cook took him on as his money handler in the 1990s. But what Cook didn’t know was that his brother, whom he adored, was withdrawing hundreds of thousands of dollars at a time from his accounts and stashing the money everywhere from potted plants to Tupperware containers filled with spaghetti sauce.
The theft culminated in a $3 million withdrawal, after which McCauley disappeared.
“This is how brazen he was,” Cook says in the documentary. “He went to the State Street Bank of America. He walked in with a check from him to him, endorsed for $3 million, and he said to that bank manager, ‘I need the cash today.’ And he put $3 million in duffel bags, and he walked out, and he put ’em in a rented f---ing SUV. Was the point to just bury me alive with nothing left?”
He adds, “The last three words Darryl McCauley ever wrote to me as the person I knew was, ‘To the future.’ That’s it. That was my goodbye letter from the brother I thought I had.”
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Dane Cook in ‘Funny Money: The Dane Cook Story’Credit: courtesy Upstream Flix
McCauley was ultimately arrested in 2008 and charged with stealing $12 million from Cook while acting as his business manager. He pleaded guilty to larceny, embezzlement and forgery in 2010 and was sentenced to six years in prison. He was also ordered to repay the $12 million to Cook.
Seeking answers, Cook made McCauley an offer: He would release him from the over $12 million restitution obligation in exchange for an interview for the documentary, which would include a face-to-face meeting between the brothers. McCauley declined.
As of November 2023, McCauley was reportedly making restitution payments of just $50 per month. He was working as a FedEx driver at the time. “If you’re missing any packages, I think I know who you can speak to,” Amann quips in the film. In 2024, McCauley had repaid $3,900, according to the documentary, leaving an outstanding balance of $12,088,130.34.
Dane Cook in ‘Funny Money: The Dane Cook Story’Credit: courtesy Upstream Flix
McCauley’s now ex-wife, Erika McCauley, was sentenced to two and a half years in connection with his crimes. “Everybody has thought that I am 100% guilty. In reality, the only thing I’m really guilty of is being gullible and trusting my husband,” Erika, who participated in the documentary in exchange for her portion of the restitution owed, says. She was arrested after an undercover sting operation revealed that she had attempted to invest $400,000 of the stolen money.
When asked at the end of the documentary if he had anything to say to McCauley if he was watching, Cook kept it simple: “To the future.”
Funny Money: The Dane Cook Story is now available to stream on VOD.
on People
Source: “AOL Entertainment”
