According to the author of Jimmy's book "Last Mafioso" Ovid Demaris, it was the JFK thing that messed up his relationship with Chicago, at least that was part of it. Fratianno claimed that Roselli told him about the whole thing, and how it was all "bullshit". Originally, Roselli was supposed to have had the ambition to have the government "by the balls", and he used the Castro situation to do it. Maheu (I think that was one of the agents last name) would have contact with Roselli, they'd tell Roselli the ideas, and Roselli would follow with ways that he and cohorts could get them done through their contacts in Cuba. Roselli had no contacts in Cuba, seeing as that was now the Castro state, their contacts were out of there, or not doing nothing. Roselli supposedly strung them along the entire time, with stories of himself and his contacts being on boats that were shot down in the water by Castro forces. It was all bullshit. According to the author, Roselli confessed that the poison shoe polish (there was supposedly an idea to have Castro's boots polished with polish that would make his beard hairs fall out. Comical stuff), the liquid they wanted to put in his drink, and the things they were going to use to poison his food was supposed to go back to Trafficante's guys and then on to Cuba to the assassin's, but according to Jimmy & DeMaris, Trafficante sat on it and never made a move. I think Trafficante never wanted to step another foot in Cuba after he was imprisoned there. But the death concoctions always stopped at Trafficante. And they were either, flushed down the toilet, thrown away, and simply forgotten about. Roselli eventually used the scheme as the reason for Castro being behind the JFK assassination as pay back for that Mob/CIA plot & the Bay Of Pigs.



But this was all Roselli's plan to have the government "by the balls", eventually they found out they were being strung along, and the Warren Commission was created. Those involved in the plot had to protect their ass, those who weren't didn't want the heat. They killed Giancana for his involvement. And then they killed Roselli, and along with Johnny went Jimmy's relationship with Chicago really. I guess they may not have really trusted him. All of that is a pretty interesting theory on the JFK hit from a mobster and his co-author.