If you finnish the cuban missions, Unberto Robina gives you a call and says that Tommy is a real cuban now...
But Tommy was betraying him the whole time, he also worked for Auntie Poulet and the haitians. Tommy killed dozens of cubans and he blew up all the ships from the cubans, they are making a living from the seatrade, so Tommy caused a lot of problems.
Of corse he also killed hatians and destroyed the factory since he worked for the cubans as well, but i think Poulet knows it, the haitians starts hating you and she keeps calling you to stay away from their hoods.
The hatians also attacks you and your bodyguards in Kaufmanns Taxi.
But Tommy stays cool with Alberto and the cubans. Kinda naiv and dumb from him , if you ask me ( even if he said Tommy is two faced during a mission)