According to Front Page Detectives, Jackson was arrested a second time on December 31, 2003. Billboard reports he parked his car in a no-standing zone outside of a New York nightclub. Police searched the car because of its tinted windows and found two loaded guns inside. Although he was charged with two counts of criminal possession of a weapon, Jackson posted bond and was released from jail. In May 2004, he took a plea deal to avoid jail time after being charged with three counts of assault and battery.

Per CNN, Jackson was once again in legal hot water in 2013 for allegedly assaulting his ex-girlfriend. He faced five charges and jail time. The charges, however, were dropped and he was given probation and ordered to pay fines (per Reuters).

Jackson's final arrest was in 2016. Insider reported that the rapper was performing in St. Kitts — an island where the use of profanity in public is banned. Jackson used the word "mother f*****" on stage and was promptly arrested. He went to court a few days later and paid a fine. In 2005, Canada almost banned Jackson for his criminal history. He was eventually allowed to enter the country. In 2020, Page Six reported that Jackson had used his real-life prison experience as inspiration for his series "For Life."

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