Dave Winfield earned the nickname in 1981, his first season with the Yankees. After starring for bad teams in San Diego, Winfield signed a big free-agent contract with the Yankees, with New York hoping he could replace the production of Reggie Jackson. Winfield played very well in 1981, leading the Yankees to the World Series, but in the Series, he fell flat, batting .045 with only one RBI in the six-game loss to the Yankees. Furious, George Steinbrenner instantly labeled Winfield "Mr. May," meant as a direct comparision to Jackson, known forever as Mr. October.
Winfield was crushed. And he never got a chance to redeem himself. Despite outstanding play from Winfield for the rest of the 1980s, the Yankees never went back to the postseason, so Winfield never got a chance to erase his Mr. May moniker.
By 1992, Winfield had been away from New York for a year and a half, going first to California and then to Toronto. Instead of a fleet, Gold Glove-caliber outfielder, he was a 40-year-old designated hitter, but he was exactly what the young Blue Jays needed. After years of near-misses, the Blue Jays finally had a roster good enough to win in 1992, but they were still a young team. Winfield's presence gave them the veteran leadership they needed to clear the last hurdle.
Winfield helped in the ALCS, hitting two home runs as the Blue Jays beat Oakland in six. Though outshined by several of his younger teammates, Winfield felt relieved with his two home runs and generally good play. He was finally able to get past his failures of more than a decade ago.
Then came the World Series against Atlanta, and Winfield's struggles began again. He only got four hits through the first five games, and no extra-base hits. Despite this, though, the Blue Jays entered game 6 in Atlanta with a 3-2 series lead, needing just one win for their first championship.
Again, Winfield's struggles continued, as he went 0 for his first 4. Still, the Blue Jays were one out from a World Championship before Atlanta's Otis Nixon hit a game-tying single, the second time in that postseason that Atlanta had gotten a season-saving hit when they were an out from elimination. This time, though Atlanta couldn't win it in regulation, so they went to extra innings.
After a scoreless 10th, Toronto put two runners on base with two outs in the 11th. Up came Winfield. This was his opportunity. This was his chance to put the Mr. May nickname away for good. With the two fastest runners on the team on base, it would only take a single to give the Blue Jays the lead, and a short double would be all it took to give them a two-run lead.
Facing Charlie Liebrandt, Winfield alternated balls and strikes, working the count full. With two outs, the runners would be going. Any hit now would almost certainly score two. Winfield dug in, waiting for Liebrandt to deliver.
It wasn't a hard-hit ball, just well-placed. A slow bouncer that went just over the bag at third and down the left-field line. It was more than enough, though. Devon White scored easily from second, Roberto Alomar flew around the bases to score from first, and Winfield ended up on second with a double, his first extra-base hit of the series and, dating back to 1981, his first extra-base hit of any kind in a World Series.
As Winfield stood on second, it all came back to him. All the years of torment and pressure that he wasn't good enough to be a True Yankee, all the years of being called Mr. May, all erased. It didn't matter now. He had delivered the hit that put his team three outs from the title. When the Blue Jays got those outs in the bottom of the inning, Winfield was officially redeemed.
Winfield stayed in the Majors for three more seasons, closing up in 1995 with Cleveland. Though those Indians tore through the American League to get to the playoffs, Winfield wasn't on the postseason roster. His double in the 11th inning of game 6 of the 1992 World Series was his final postseason at bat.
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