Winfield is a Hall of Famer, a member of the 3,000-hit club and is one of three people to ever be drafted by four sports leagues (MLB, NBA, NFL, ABA). Yet, some people only remember him from this quote in 1985 by Yankees owner George Steinbrenner: “Where is Reggie Jackson? We need a Mr. October or a Mr. September. Winfield is Mr. May.”
Ouch! Steinbrenner was saying that Winfield was someone who only put up big numbers in the regular season, or in May, rather than the postseason or the push for the postseason, which would be September and October. The “Mr. May” nickname wasn’t helped when Winfield hit a dismal .182 in his only postseason appearance with the Yankees. But, ironically, when he retired after the 1995 season, Winfield had the exact same career batting average (.277) in May as he had in September and October.