Pepitone joined the Yankees in 1962, playing behind Moose Skowron at first base. Fun-loving and carefree, he spent his $20,000 signing bonus on a fancy car and a motorboat. Pepitone had a powerful swing and an excellent glove, and some of Pepitone’s tougher friends thought he should be the regular first baseman ahead of Skowron. They offered to help Joe out by breaking Skowron’s legs; Pepitone declined. The Yankee brass believed he could handle the job and before the 1963 season traded Skowron to the Dodgers. Pepitone responded admirably, hitting .271 with 27 HR and 89 RBI. He went on to win three Gold Gloves, but in the 1963 World Series he made an infamous error. With the score tied 1-1 in the seventh inning of Game Four, he lost a routine Clete Boyer throw in the white shirtsleeves of the Los Angeles crowd, and the batter, Jim Gilliam, went all the way to third base and scored the Series-winning run on a sacrifice fly. He redeemed himself somewhat in the 1964 Series against the Cardinals with a Game Six grand slam.
The ever-popular Pepitone remained a fixture throughout the decade, even playing centerfield after bad knees reduced Mickey Mantle‘s mobility. After the 1969 season he was traded to the Astros for Curt Blefary. Later he played for the Cubs and finished his major league career with the Braves.
Pepitone briefly played baseball in Japan in 1973, but the regimented Japanese didn’t know what to make of the free-spirited Pepitone, who was unhappy away from home. He jumped the Yakult Swallows in 1973 while hitting .163, becoming a one-man international incident. In the 1980s he was arrested on gun and drug charges while hanging out with the wrong people and served a small amount of time in prison; he eventually got out on a work-release program, working in the Yankee front office.