The ties between the Chicago Outfit and JFK where long and deep. Plus the Outfit and CIA 'had a thing'. And like Oswald, they don't/didn't like being a patsy (sucker) either.
Keep in mind, E Howard Hunt's wife, Dorothy, died in a 1972 Plane Crash while it was in its landing approach into Midway Airport (SW side of Chi). She had $10K in cash in her purse.
(I'll leave it at that.)
Good grief.