In October 2010, Darryl McCauley admitted to embezzling millions from Dane Cook between 2004 and 2008, for which he was sentenced to five to six years in prison, the Boston Globe reported at the time. McCauley, who had been managing his brother's business since Cook started in the early 1990s, according to Entertainment Weekly, continuously transferred his brother's money to his own personal account, per the Boston Globe. At one point, McCauley wrote himself a $3 million check using the company's funds, the report further detailed. "For several years, Mr. McCauley abused his position as a family member to gain Mr. Cook's trust, and stole millions of dollars for his own personal gain," said Attorney General Martha Coakley, per the Boston Globe.
The following month, McCauley's wife, Erika, also pleaded guilty to stealing her brother-in-law's money and was sentenced to up to three years, according to United Press International. Both were also ordered to pay restitution to Cook. The couple spent the embezzled money on homes, jewelry and businesses, both in Maine and in Florida, per UPI.
Speaking on "Your Mom's House" podcast, Cook said he never noticed unusual transactions on his business accounts because he simply trusted his brother. Cook was the one who contacted the Massachussetts attorney general's office, thinking that McCauley had probably also stolen tax money from the state. A year later, Cook faced his brother in court. "I was really unbelievable," Cook said.
