I don't know why people have this opinion that Paul Castellano was just some yuppie, used to only the finer things in life and couldn't handle a jail sentence. The guy was a street guy majority of his criminal career, he did the blue collar rackets, he was in the streets.
At the end of his life he was a yuppie. He wasn't a street guy anymore. The only time he played a street guy was when capos showed up at his house and even then they thought of him as a yuppie. Why else you think most thought Neil would be boss instead of him? Yes he was once a street guy when he was younger, but Carlo gave him the freedom to become a blue collar guy that he became and it cost him in the end.
The only time he played a street guy was when capos showed up to his house? The guy oversaw extortion rackets, loansharking, hijacking, traditional blue collar LCN rackets. One usually has to be street smart and have a bit of an edge to successfully run those types of crimes. Him getting older and preferring to be more of a reserved, businessman, Detroit-like don doesn't change who he is, I don't think. He simply found a way to produce more money for his crime family, and preferred to be an enigma to LE. Most of the successful bosses took the same approach, but most weren't also farsighted enough to see that white collar crimes is were it's at. I think the possibility of him taking a life sentence and keeping his mouth shut is a lot more realistic than people think.
