Lucky.....if we're counting the time when both he and Vito were active bosses on the street, and not when they were behind bars/deported.

Lucky had close contacts with other families.....Anastasia and Lucchese were underbosses, but were closely aligned with Lucky. And Lucky had the ear of the Jewish mob through Lansky, Siegel, and Lepke. Through Costello, he had political contacts and he had Joe Adonis in his corner.

Meanwhile, Vito was supposedly anti semitic and didn't get along with Lansky and Siegel. Vito and Anastasia hated each other, and he tried to whack Costello. According to the book, Joey the Hitman, Genovese also tried to whack Lansky.

Charlie had more power and influence. Wealth? I'd give the nod to Genovese due to the margins with narcotics, but that's just a guess.