Why did Carlo Gambino pick Paul Castellano to be his successor? From what I have read, the choice of Castellano did nothing but fracture the Gambino family, leading to the eventual coup d'etat of John Gotti. The rank and file deeply resented Castellano because he was viewed as having become boss solely because he was a relative of Gambino. He was a white collar criminal without experience on the streets. Furthermore, Castellano added insult to injury by refusing to mix with his men and building an opulent "White House." The favored choice to succeed Gambino was underboss Neil Dellacroce, John Gotti's mentor, who was known as a "hoodlum's hoodlum." According to Jerry Capeci, in the years after Gambino's death the family basically split into two branches--the "Paul branch" and the "Neil branch." So why did Gambino do it? For someone who was (and is) considered an excellent godfather, this seems like a glaringly bad decision.

Even the very wise cannot see all ends.

Castellano was both Gambino's cousin and in-law. That probably is the primary explanation.

Perhaps Gambino justified it to himself by reasoning that the future of the Family would have been better secured by the relatively white-collar/smooth Castellano instead of the frightening and rough around the edges Dellacroce.

There's a lot of examples in corporations where the number 2 guy feels entitled to the top spot because of his deep loyalty and long experience but precisely because he is so wedded to the old way of doing things, doesn't get the nod.

In addition, Dellacroce was in prison for tax evasion at the time of Gambino's death. That made his criminal profile higher than Castellano's--Big Paul had served a short term for armed robbery as a youngster and, except for getting busted at the Apalachin meeting in '57, had no further brushes with the law. At the time of his succession, he was a more or less legitimate businessman (wholesale meat and poultry) and was in charge of the family's "white collar" rackets. So, I'm assuming, Gambino thought Castellano would attract less law enforcement attention as Don than would Dellacroce.

I agree Lilo. Gambino and Castellano were also Sicilian. Dellacroce and Gotti were both Napolitano.