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Dane Cook's Brother Embezzled Millions from Him – Did the Actor Ever Recover His Money?

Milla Sigaba
Aug 06, 2022
06:30 P.M.
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Comedic star Dane Cook discovered his brother had stolen millions of dollars from him for years. During an interview with YMH Clips, Dane shared how he found out if he ever got the money back and what happened to his brother.

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In 2003, Dane debuted his comedy album "Harmful If Swallowed," which peaked at number two on the Billboard Comedy Album charts. After the success of his first album, he released four more albums that reached number one status and released two more albums over the next seven years.

After the massive success of his comedic albums, Dane asked his half-brother, Darryl McCauley, to help him manage his finances, but things turned out for the worst when Dane sent his brother to jail in 2010.

Dane Cook and Kelsi Taylor arriving on the set of “Jimmy Kimmel Live” in California on February 14, 2019 | Source: Getty Images

Dane Cook and Kelsi Taylor arriving on the set of “Jimmy Kimmel Live” in California on February 14, 2019 | Source: Getty Images

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HOW DID DANE COOK DISCOVER HIS BROTHER WAS STEALING FROM HIM?

Despite having different fathers, Darryl was Dane's best friend. In his interview with YMH Clips, Dane shared that his brother used to work as a corrections officer before he asked Darryl to leave his job and work in his brother's business.

In Darryl's role as business manager, he had a monthly salary of around $12 500, including selling merchandise at events and handling Dane's emails and website.

His title as business manager was about to change when Dane announced he was buying a house in California. Due to legal reasons, he could not be a resident in one state and have his business run in another. Dane's business was being run in Boston, Massachusetts.

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Darryl did not take the news well and was reluctant to transfer documents to Dane's new business manager in California, who thought Darryl's behavior was off-kilter. Dane sensed something was not right.

Dane Cook at the SiriusXM Studios in New York on October 7, 2019 | Source: Getty Images

Dane Cook at the SiriusXM Studios in New York on October 7, 2019 | Source: Getty Images

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Dane said he woke up in the middle of the night, turned to his girlfriend, and said, "I think my brother stole all my money!" The following day he went to Bank of America on the corner of Crescent Heights in Santa Monica.

After the bank manager's help, Dane discovered that there was nothing in his corporate account. He called the Attorney General of Massachusetts' office and reported that his brother had stolen from him and had probably stolen from the state, too.

The last time Dane and Darryl had communicated before Dane realized his brother was stealing from him was a letter he wrote to Darryl, assuring him things would be fine. Darryl ended his response back with, "to the future."

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Dane Cook at the premiere of Starz’s “American Gods” in California on April 20, 2017 | Source: Getty Images

Dane Cook at the premiere of Starz’s “American Gods” in California on April 20, 2017 | Source: Getty Images

DANE COOK'S BROTHER STOLE MILLIONS OF DOLLARS FROM HIM

Dane initially could not get into his accounts at Bank of America- his brother had given him fake account credentials. In the past, Dane had never looked at his accounts; he trusted his brother and felt there was no need.

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As it turns out, Darryl embezzled millions of dollars over the years from Dane. He would forge checks and transfer money without Dane's awareness or consent. On one occasion, he wrote himself a 3 million dollar check from Dane's account.

The judge at Darryl's sentencing said his actions were motivated by entitlement. Thus Darryl pleaded guilty to twenty-seven counts of larceny over two hundred and fifty dollars and three counts of forgery, embezzlement, and other charges.

Dane Cook at the 34th Santa Barbara International Film Festival in California on February 7, 2019 | Source: Getty Images

Dane Cook at the 34th Santa Barbara International Film Festival in California on February 7, 2019 | Source: Getty Images

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His wife, Erika, was not only aware of her husband's illegal activity but also participated; the two had purchased properties using the stolen money. She also faced criminal charges, including larceny and receiving stolen property. Present on his brother's sentencing day, Dane felt like he was in a movie; he struggled to believe it was all true. He said:

“Seeing him and looking at him that day in the courtroom was surreal because he looked like a shark, he just had dead, nothing eyes. Nothing, no emotion. I didn't look at a person I knew, I was looking at a stranger.”

DID DANE COOK'S BROTHER EVER REPAY HIM?

Darryl was sentenced to five to six years in prison and another ten years of probation after his release. The court ordered him and his wife to pay Dane twelve million dollars. Erika was sentenced to two-and-a-half to three years in prison with thirteen years of probation.

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Dane Cook during an interview on “Jimmy Kimmel Live” in New York on February 14, 2019 | Source: Getty Images

Dane Cook during an interview on “Jimmy Kimmel Live” in New York on February 14, 2019 | Source: Getty Images

About a year and a half later, police found an estimated eight hundred thousand dollars hidden in a wall by Darryl, which was returned to Dane. His brother had not been paying his taxes for years, and Dane had to pay even more tax penalties.

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He said he had to pay the penalties for his brother's actions if he wanted his money back:

“Once they convicted him, then the IRS actually sent me a check like, ‘okay, yeah, now it's good, you're right, it was his responsibility.’”

Dane Cook’s half-brother Darryl McCauley at the Woburn District Court in Massachusetts on January 15, 2009 | Source: Getty Images

Dane Cook’s half-brother Darryl McCauley at the Woburn District Court in Massachusetts on January 15, 2009 | Source: Getty Images

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Despite stealing millions of dollars from his brother, what did not make a bad situation worse was that Darryl could not take Dane's money in stocks. Dane had about three hundred and twenty-five million dollars tied up in stocks.

He used the money to rent arenas for his performances, pocketing the profit from his shows and using it to keep himself and his business afloat.

Despite finding a silver lining in the situation, Dane and his brother are not on speaking terms. Dane felt betrayed by his brother, who had trusted Darryl with his money and business, and he ended up stealing from him.

Dane Cook performing during New York Comedy Festival in New York on November 4, 2016 | Source: Getty Images

Dane Cook performing during New York Comedy Festival in New York on November 4, 2016 | Source: Getty Images

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DANE COOK SAW HIS STORY ON "JEOPARDY"

Dane's ordeal with his brother was the subject of a question on the game show "Jeopardy." The game show's host, Alex Trebek, asked a contestant, "Dane Cook's half-brother and business manager stole millions from the comic, this crime of misappropriating bank funds," to which the contestant correctly answered, "What is embezzlement?"

Fortunately, Dane can find humor in the situation; he took to Twitter to share a clip of the show, captioning it "#my life."

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