Jose Canseco first had problems with the law back in 1989. According to the South Florida Sun-Sentinel, Canseco was driving recklessly and refused to stop when an officer tried to pull him over. He proceeded to drive for 15 miles without pulling over and as punishment, he was fined $500. Shortly after, in April 1989, Canseco was on the University of California-San Francisco campus to have a wrist injury examined when police discovered a loaded gun in his car, The New York Times writes. He had no permit and because he was on a state university campus made it a felony. As the Los Angeles Times later reported, he pleaded no contest to the gun charges.

Sometime after, Canseco was fighting with his wife, Esther Canseco, and hit her BMW the Porsche he was driving, according to a later publication by The New York Times. He was charged with a third-degree felony of aggravated assault. He pleaded not guilty. Then in November 1997, Canseco hit his then-wife of one year, Jessica Canseco, and pleaded no contest a later publication by The New York Times noted. He was sentenced to one year of probation and had to participate in counseling.