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This likely coincides with him taking the blame for a crime committed by Armando and Henrique (neither of whom were caught) and going to prison.During this stint, also two years, he went from being very skinny to being quite muscular.
It's unproved, but this blame comes from his lovers, and he gets angry when somebody else talks about that.
In the last cutscene, Luis is thanked by Tony as he 'saved' his business.
Then Yusuf arrives and the three talk about what their near futures, as the player is to decide what happens next.
He began doing work for his mother and friends (Momma's Boy, Corner Kids and Clocking Off) then began helping Rocco with his work on missions for Tony; he meets multiple gang officials in peace attempts, all of which wage war nearly killing him and Tony. Things only turned worse for Tony after a Bahama Mamas meeting in the mission Boulevard Baby also went wrong.
Luis, Evan Moss and Gay Tony would later buy ,000,000 worth of Diamonds, but lose them at the hands of Johnny Klebitz, who kills Evan, but was fortunately able to reclaim them that much later.