Mr. May
"I let Mr. October get away, and I got Mr. May, Dave Winfield. He gets his numbers when it doesn't count."
-George Steinbrenner III
Dave Winfield had himself a Hall of Fame career, mostly from his work with the San Diego Padres and New York Yankees. When Mr. Steinbrenner brought him to the Bronx, it was with the intent to bolster a Yankees team that would win several more championships. But with the exception of 1981, the Yankees were good, but never good enough to reach the postseason. No team won more regular season games in the 1980s than the Yankees, but it brought them 0 rings, and for The Boss, that wasn't good enough. And the focal point of this frustration was centered on their high price acquisition, Dave Winfield.