Because he is a uneducated street guy that did not get it when his father uncle and loads of good dudes could have learned from but instead he wanted to be in the bar and at the end of a straw when he was coming up.

He is / was as lucky as any gangster ever , but he did not get business!!! other then street businesses and in order to run a family you need blue collar and white collar knowledge ..... look at Gotti and Castellano ..... it ‘s mandatory to run a successful Family.