May did get a crack at postseason play, but not with the White Sox. On May 18, , he was traded to the Yankees for pitcher Ken Brett and fellow outfielder Rich Coggins. The deal was made while the Yankees were in a heated pennant race. That year, he hit .278 and the Yankees went to the World Series. During the ALCS, May went 2-for-10 with a double and a walk. In the World Series against the Cincinnati Reds, he did not get a hit in 9 at bats and ended up with a .105 batting average in the postseason.