Michael O'Sullivan; Michael O'Sullivan, Jr.; the Two Jacks [Jack Grizzard; Jack Fallon]; Tom Pendergast; Harry Truman (cameo); Johnny Lazia; Vito; Al Capone; Connor Looney; Frank Nitti; John Looney; Emeal Davis; Caitlin O'Daly; Katie O'Daly
Michael O'Sullivan attacks Kansas City organized crime in order to put pressure on the Capone gang. Connor Looney escapes Frank Nitti's protective custody and kidnaps O'Sullivan's old love Katie O'Daly as bait to lure O'Sullivan in. O'Sullivan frees Katie, but the Two Jacks capture Looney and smuggle him back to Nitti. The two O'Sullivans take to the road once again.