Dane Cook Recalls Brother’s “To the Future” Goodbye After Theft

Cook had relied on McCauley since their childhood in Arlington, Massachusetts. After McCauley was injured while working as a corrections officer, Cook brought him into his entertainment business. What began as help with everyday tasks and merchandise sales grew into responsibility for Cook’s finances and business affairs as his career surged in the 2000s.

Cook says he started questioning the arrangement when he moved his finances to a larger management firm. McCauley became hard to reach, and requests for records went unanswered. In December 2008, Cook says, McCauley withdrew $3 million in cash from a Bank of America branch, carrying it away in duffel bags. Cook later found a little more than $100,000 in checking and about $300,000 in stocks, while facing nearly $6 million in unpaid taxes, according to his account.

Investigators found cash concealed in potted plants, wall safes and food containers, including spaghetti sauce and a freezer box of Bagel Bites. McCauley and his wife, Erika, also spent money on properties, cars and vacations. McCauley was arrested in 2008 and pleaded guilty in 2010 to larceny, embezzlement and forgery. He was sentenced to five to six years in prison and ordered to repay the money. Erika also received a prison sentence for her role.

Cook says touring helped him rebuild his finances, but he alleges McCauley pays $50 a month toward restitution and had repaid only $3,900 by 2024. The brothers last met at McCauley’s 2010 sentencing, Cook says. McCauley declined Cook’s offer to forgive the restitution in exchange for appearing in the documentary and meeting on camera. Erika, now known as Erika Montsesi, appeared and said she learned of the theft afterward. Cook says he still believes others may know more about the money’s whereabouts.