Matusow has had several personal problems. He has battled drug issues, including a six-month stint in jail in 2004 and 2005 after being caught providing ecstasy and prescription painkillers to an undercover police officer who pretended to befriend Matusow and gained his trust. After several months of an official Las Vegas Metro Police "Sting Operation", Matusow was arrested and charged with six category A Felonies, all drug related. A plea deal was later reached where Matusow was incarcerated in the Clark County Detention Center for six months.