June 2001 - Signs with the Chicago White Sox.
November 2001 - Along with twin brother Ozzie, Canseco is arrested and charged with battery for a fight that occurred on Halloween at a nightclub in Miami. Canseco pleads guilty and is sentenced to three years' probation, community service, and anger management classes.
May 2002 - Retires from Major League Baseball.
February 2003 - Is jailed for violating his probation after he fails to take anger management classes or begin his community service.
March 2003 - After spending a month in jail, Canseco is released and sentenced to two years of house arrest and three years of probation.
June 2003 - Is arrested and jailed for violating probation after testing positive for steroids.
August 2003 - Florida prosecutors drop the drug charge against Canseco, and he resumes house arrest.
2005 - Canseco's book, "Juiced: Wild Times, Rampant 'Roids, Smash Hits and How Baseball Got Big," is released. In the book, Canseco claims that he used steroids with Mark McGwire, Rafael Palmeiro, Juan Gonzalez, Ivan Rodriguez, and Jason Giambi.
2008 - Releases second book "Vindicated: Big Names, Big Liars, and the Battle to Save Baseball."
2012 - Files for bankruptcy in Nevada.
May 2013 - Is named as a suspect in a sexual assault investigation, according to the Las Vegas Metro Police Department.