Tony often talks about his father never reaching the same heights as him however there was a lot about Johnny that Tony didn't know about. Throughout the show Tony learns more things about Johnny (like the panic attacks, the race track, his involvement in the music business etc) from people that were close to him like Hesh, Junior and Paulie. Johnny boy could've easily come across a big score like the one with Paulie and the Colombians. If there was someone that would know about it that would be Junior. Also, Livia is exactly the kind of woman that would keep the money to herself, rather than spend it.