If you’re a millennial caveman like me, then you remember around 2006-2009, Dane Cook was the king of the world. During this time, nobody was making more noise (figuratively and literally) than the Massachusetts-born comedian.
Cook’s colossal success wasn’t without its controversies and pitfalls; accusations of joke theft plagued the comic even at the peak of his success, and his turn to the silver screen produced several less-than-stellar films. However, the greatest obstacle Cook had to face came in the form of his own family.
Dane Cook’s brother stole millions from him
Early in his career, Cook had asked his half-brother, Darryl McCauley, to manage his finances. According to The Hollywood Reporter, McCauley made $12,500 a month while on his brother’s payroll. “I loved my brother,” Cook said in 2019 on the Your Mom’s House podcast. “I really did. He was my first real best friend.”
According to Cook, McCauley had sent him fake bank statements — typed up on Microsoft Word — for nearly a decade. Later in his career, when the comic bought a home in California, got a new business manager, and planned to shift his resources from Massachusetts to California, he noticed serious pushback from McCauley.
One day, after a series of discussions with his new business manager, a sudden realization hit the comedian. He rushed to a Bank of America in Santa Monica, where he quickly discovered that not only were his corporate accounts empty, but much of the info his brother had given him, such as a supposed federal ID number, was fake. “I’d never looked at my bank. I never looked,” Cook said on the YMH podcast. “I just trusted him.”
Cook quickly brought the matter to the Attorney General’s Office of Massachusetts. McCauley, along with his wife, Erika, who was in on the whole scheme, were subsequently arrested. A year later, Cook saw his brother in court. The comedian described the experience as “surreal,” noting that his brother had “dead, nothing eyes.” When YMH co-host Tom Segura asked whether it was just general greed that motivated McCauley, Cook responded with, “entitlement.”
According to the The Boston Herald, McCauley had also used Cook’s credit card for “vacations, jewelry and home decorating.” These charges totaled around $350,000. Additionally, McCauley and his wife invested millions in Florida restaurants and a resort in Maine; the former also forged his brother’s signature to write a check for $3,000,000; he subsequently hid the money across big cities and towns, according to prosecutors representing Cook. The comic explained on the YMH podcast the police were able to retrieve $800,000 that was hidden in the walls of his brother’s home.
Cook’s brother was a former corrections officer
In 2010, McCauley was sentenced to five to six years in prison for stealing money from the comedian (per CBS News). His wife, Erika, was sentenced to three years, and the two were ordered to repay Cook $12 million (via CNN). Ironically enough, according to Cook, McCauley was a former corrections officer at a Massachusetts prison prior to becoming his brother’s manager.
Years later, on a July 2022 episode of Logan Paul‘s Impaulsive podcast, Cook discussed the ordeal, saying, “It was the worst betrayal I’ll ever experience in my life … I’ve never been sadder in my entire life.”
The comedian also explained that his brother had already fully served his sentence, but that had he no idea where McCauley currently resided. However, he did mention to Paul that he was working on a documentary about the incident, and mentioned he was open to sitting down and talking with his brother.
The documentary is expected to release in 2024 (via NBC). Whether Cook’s brother will make an appearance, however, remains to be seen.
