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In 1959 Dragna was arrested with mobsters Joe Sica, John "Frankie" Carbo, Frank "Blinky" Palermo, and Truman Gibson for extorting Jackie Leonard the manager of boxing champion Don Jordan in 1958.
Two years later, Mr. Gibson and four co-defendants – Frankie Carbo, once described by the New York district attorney's office as "the underworld czar of boxing", Louis Tom Dragna, Joe Sica, and Frank Palermo – were convicted in federal court of conspiracy and extortion in an effort to siphon off earnings from the welterweight champion Don Jordan.