I don't remember EVERYthing from Dante's timeline, so don't quote me 100% BUT
Pac was supposed to perform benefit concerts and organize a youth baseball league as part of his community service. He did neither (He planned to, though) so the Judge gave him more time to do so when he went to court in summer 96. He was pulled over several times, usually possessing weed at the time. (This may have been before '96, not sure), he failed several drug tests. He left the country withoutr permission (He went to Italy in Summer 96.) His next court date was September 12, 1996 (The day before he died). He likely wouldve gone back to jail, plus he assaulted Orlando Jones and was rumored to have assassulted Sam Sneed. It was also illegal at the time to wear a bulletproof vest in public (Remember ODB?)
So I imagine everytime he was stopped, he had weed, guns, and a bulletproof vest in his possession, plus he was probably under the influence of alcohol, even though he DIDN't drive.
He was not paroled from his first sentence, he was merely bailed out. He still had 3-4 years left on his first sentence, so he could've gone back to jail till '99 like Suge did.
