I would say that Albert Anastasia even had money for a long time before he was boss. He may not have been the "don" for decades, but he was a top mobster for decades. However, he was more John Gotti than Carlo Gambino.
And yes, I have to agree with your assessment of Anastasia. He was always an important guy, so I'm sure he made money, even before he ascended to boss.
But, its funny you say what you did, because as I wrote this piece, Gotti came to my mind also, as I compared the two men. Similar styles, big gamblers, rose to boss, but blew nearly everything they had.
