The disputes led to Steinbrenner referring to Winfield as "Mr. May," comparing him to Reggie Jackson who was Mr. October, since Jackson had a knack for getting big hits in the postseason, while Winfield went 1-22 in his only WS appearance with the Yankees in 1981. Despite Winfield and Don Mattingly, the Yankees struggled during the rest of the 1980s. Steinbrenner's frustration got the best of him, and he continued to blame Winfield for the team's struggles. Winfield was injured before 1989 and ended up missing the entire season. It came to a head when it was proven that Steinbrenner had paid gambler Howie Spira $40,000 to dig up damaging information on Winfield. This led to a lifetime ban for Steinbrenner, though he was reinstated two years later.
There is no question Winfield had his best years with the Yankees. Over the nine years he played for the Yankees, he batted .290 with 205 HR and 818 RBI, which averaged out to over 20 HR and 90 RBI a season. The average numbers would be higher not counting his partial season in 1990, where he was traded on this day to the Angels. Winfield had initially rejected the trade, but seven days later agreed on an extension with the Angels where he would be paid into the 1991 season. He went on to hit .275, 19, 72 with the Angels in 112 games, winning the 1990 comeback player of the year award.
Collectively, Winfield finished his career with 3110 hits, 465 HR and 1833 RBIs to go along with his .283 average in his 22 year run. Those numbers made him a first ballot Hall of Famer. Though the bulk of his numbers were put together in a Yankees uniform, Winfield chose to go into the HOF wearing a San Diego Padres cap. He will be remembered as a Yankee, regardless of his dislike for Steinbrenner.