If he wanted to be a gangster, he certainly wasn't built for it. Sure he beat up Benny (oddly enough), but notice how he runs off after those indian protestors cause a riot on Colombus day... He's running towards the car lol.

As mentioned, the burning of the restaurant and Tony denying it broke his heart. On top of that he can nearly make ends meet. Charmagne is constantly nagging him, and his own employees (martina), steals from him. His 50k loan went to shit putting his whole relationship with Tony at stake. The guy hadda lot of problems.