Dane Cook
Dane
Cook hired his half-brother brother Darryl
McCauley as his finance manager and left him in charge of his finances for most
of the 90s. It doesn’t come as a surprise that McCauley ended up
stealing $12 mil from Cook. When Dane noticed that the money was missing alerted
authorities, and in 2008, Cook’s half-brother and his wife were convicted of larceny
and embezzlement. The couple was ordered to pay Dane Cook back and they also
received probation and prison sentences.