During the height of his fame, Dane Cook relied on Darryl to manage his money. While the comic passed the time looking at himself naked in the mirror and writing self-aggrandizing jokes about what he saw there, Darryl was stealing millions of dollars from him. The Boston Globe reported in 2010 that Darryl had pleaded guilty to embezzling millions from his famous half-bro while working as his business manager, a crime that landed him in a Massachusetts state prison for five to six years. The Attorney General said in a statement after the trial that from 2004 to 2008, Darryl had simply transferred money from Dane Cook’s bank accounts to his own or just wrote massive checks to himself. One of his forged checks was cashed for a whopping $3 million.
According to The Hollywood Reporter, Dane said that his brother’s actions were “a terrible betrayal.” He was paying Darryl $12,500 a month, so the discovery that he was stealing millions more on top of such a generous salary had to hurt. The court ordered Darryl to repay Dane $12 million. Darryl’s wife Erika also received prison time for her role in the scheme.
But if you’re worried about Dane, don’t be. Even though his brother stole millions from him, and even though you went the whole 2010s without even thinking about him, he’s still doing pretty well financially. Celebrity Net Worth reports that he’s still got a cool $35 million in the bank.