Construction and Sanitation was where he made his big money. He also dealt in gambling/loan sharking like his father, which was how they took over Satriales and became a nice legit business for them. Francis Satriale got in debt with them and they took it over.

Tony in real life would have just ran his own crew and kicked up to his bosses. He was a very good earner but just way too hot headed & unpredictable to become boss in my honest opinion. I mean you look at the guy the wrong way or say something he didn't like and he would have ripped your head off. You cannot have the boss of a family with that kind of temper if you want to be successful. This was the reason they ended up going to war in the show and pretty much got eliminated.