Dane Cook Says Half Brother Behind $12 Million Embezzlement ‘Disappeared’ After Prison

Dane Cook is revisiting the $12 million embezzlement scheme carried out by his half-brother and former business manager, Darryl McCauley, saying in a new documentary that McCauley “disappeared” after serving his prison sentence and that questions remain about where some of the stolen money went.

Funny Money: The Dane Cook Story, set for release Sept. 29, examines the criminal case that led McCauley and his wife, Erika McCauley, to plead guilty in 2010 to charges stemming from the theft of millions of dollars from the comedian.

McCauley managed Cook’s finances as the comedian’s career grew and ultimately pleaded guilty to 27 counts of larceny, three counts of forgery, embezzlement, and other charges. A Massachusetts judge sentenced him to five to six years in prison. Erika McCauley was sentenced to two and a half to three years after pleading guilty to charges that included larceny.

The couple was ordered to pay Cook $12 million in restitution. Unlike a criminal fine paid to the government, restitution is intended to compensate a victim for financial losses caused by a crime. The order also led the court to examine assets belonging to McCauley and his wife, including seized cash, vehicles, jewelry and property, as authorities sought to recover money for Cook.

Cook says the convictions did not answer all of his questions. In the documentary, he asks what happened to his half-brother after prison and suggests that some of the money taken from him may never have been recovered.

“Where is he? What has he done? How does this end?” Cook asks in the film. He also says he believes more money could still be out there and that other people may know what happened to it.

Cook discovered the theft in 2008 after years of allowing McCauley to oversee his personal and business finances. Prosecutors said McCauley transferred money from Cook’s company into accounts he controlled and used the funds for personal investments and purchases.

The documentary also revisits how some of the stolen cash was allegedly concealed. Cook describes large withdrawals from his accounts, while the case included accounts of money wrapped in plastic and hidden inside empty spaghetti sauce containers.

McCauley had worked as a corrections officer before managing Cook’s finances. The theft unfolded while Cook’s comedy career was at its commercial peak, when his albums and arena tours were generating substantial income.

Cook now says he believes unanswered questions remain about the full scope of the theft and whether additional money exists. His documentary describes McCauley as having disappeared after prison, although there is no indication that he has been officially declared missing or is the subject of a current law enforcement search.