Another fellow who I think doesn't get enough credit for brains was Utica, New York's Salvatore Falcone.
He seems to have essentially been the overall "boss" of that section of New York States for many years with little interruption from law enforcement. With the one exception of when he and his brother Joe were arrested during the Prohibition Era, along with 40 or 50 of their men, he remained largely unscathed throughout his life and career.
And he was sharp enough, that by the 1940s he removed himself entirely from NYS, "semi-retiring" down to Miami, Florida where he lived quietly and successfully operated a wholesale/retail food supply firm for the rest of his days, leaving his brother at the helm as the new "capo" of Utica.
It is still believed that Sal remained as the overall leader, receiving his monthly stipend and available for consultation and council as required. He remained in the background and never got his hands dirty in the rackets. Yet, by all accounts he still seemed to live quite nicely so he must have stashed a wheelbarrow of money over the years.
The only ripple came in November, 1957 after the Apalachin Meeting. But even that, ultimately, didn't affect him.
IMO, Salvatore Falcone was a very sharp fellow.