Between 2006 and 2009, Dane Cook was an unrivaled force in the world of comedy. However, amid his colossal success, he faced significant challenges, including accusations of joke theft and a foray into films that didn’t all fare well. Yet, the most formidable obstacle Cook encountered came from within his own family.
In the early stages of his career, Cook entrusted his half-brother, Darryl McCauley, with managing his finances. McCauley, on his brother’s payroll, was earning $12,500 monthly. “I loved my brother,” Cook revealed in a 2019 podcast. “He was my first real best friend.” However, this trust proved to be misplaced.
Over nearly a decade, McCauley provided Cook with fabricated bank statements, eventually leading to a pivotal moment in the comedian’s life. When Cook relocated to California and sought to shift his financial resources, he encountered resistance from McCauley. This prompted Cook to investigate, and he made a shocking discovery: his corporate accounts were empty, and much of the information provided by his brother, including a supposed federal ID number, was false.
Cook promptly reported the matter to the Attorney General’s Office of Massachusetts, leading to the arrest of McCauley and his wife, Erika, who was complicit in the scheme. In court, Cook described the surreal experience, noting his brother’s “dead, nothing eyes.” When asked about McCauley’s motivation, Cook attributed it to a sense of entitlement.
According to reports, McCauley had also misused Cook’s credit card for personal expenses, amounting to approximately $350,000. Additionally, he and his wife invested millions in businesses and forged Cook’s signature to withdraw $3,000,000, hiding the funds across various locations. Eventually, authorities recovered $800,000 hidden in McCauley’s home.
In 2010, McCauley was sentenced to five to six years in prison, while Erika received a three-year sentence. They were also ordered to repay Cook $12 million. Intriguingly, McCauley had previously worked as a corrections officer in a Massachusetts prison.
Years later, Cook discussed the ordeal on a podcast, expressing the profound betrayal he felt. He mentioned that McCauley had completed his sentence, but Cook was unaware of his current whereabouts. Cook also revealed he was working on a documentary about the incident, leaving open the possibility of a conversation with his brother. The documentary is expected to be released in 2024, but whether McCauley will participate remains uncertain.
