45. Horace "Ho Ho" Cook
Showcase Episode: "The Arrangements"
Pete's college chum from Dartmouth has money — lots of money — and a dream: He wants to make jai alai as popular as baseball. "Ho Ho" wants to spend a fortune pushing this sport, even when Don tries to warn him off, and plans to make a matinee idol out of the the sport's star, Paxti. (This latter idea is responsible for the Clueless-worthy line, "I'm terrified of him catching balls in the face.") Sterling Cooper gets a case of "bill it to the kid" fever, since jai alai will never become the national pastime, but conning suckers is. Cook's hard-ass dad is a real piece of work, too. "My father hates Kennedy, because he knew Old Joe when they were criminals together."