Winfield was born and grew up in St. Paul, Minnesota, ultimately earning a scholarship to the University of Minnesota, where he starred in both basketball and baseball for the Golden Gophers. After hitting and pitching the Gophers to the College World Series in 1973, he was drafted in the first round of the baseball draft by the San Diego Padres. At about the same time, he was also drafted by teams in the NBA, ABA and even by the Minnesota Vikings of the NFL despite not playing college football. He remains the only man ever drafted in three different professional sports.
Winfield chose baseball, and gained another distinction after signing with the Padres. The team promoted him directly to the major leagues, a move almost unprecedented in modern baseball. But he proved up to the task, batting .277 in 56 games.
For the next several years, Winfield was a good, but not great player in San Diego, gradually increasing his power and hits totals. He burst into stardom in 1979, when he batted .308 with 34 home runs and 118 RBI, then played one more season with the Padres before becoming a free agent.
In 1981, New York Yankees owner George Steinbrenner made headlines by signing Winfield to a 10-year, $15 million contract which made Winfield the game's highest-paid player. Winfield was one of the best players in the game throughout the life of the contract, but soon had a falling out with Steinbrenner.
He helped the Yankees to the 1981 American League pennant, but then had a poor World Series, and the Yankees lost in six games to the Los Angeles Dodgers. A bitter Steinbrenner derided Winfield by saying "I got rid of Mr. October (Reggie Jackson) and got Mr. May." The Mr. May sobriequet lived with him for the rest of his career.
Winfield went on to hit 37 home runs in a spectacular 1982 season and batted .340, second in the league to teammate Don Mattingly, in 1984. He drove in 744 runs between 1982 and 1988, won five Gold Glove Awards for his stellar outfield play and was named to the All-Star Game every season.
During the 1983 season, he was involved in a famous incident in Toronto, when a baseball he threw in pregame warmups accidentally struck a bird and killed it. Winfield doffed his cap in mock sorrow, and drew laughs, but was later arrested by Toronto police for "causing undue suffering to an animal". The incident ended a few hours later with his release.
In 1989, Steinbrenner was suspended from running the Yankees for two years because of his connections to a gambler, whom he'd paid off to try to find embarrassing information about Winfield. The year was no better for Winfield, who sat out 1989 with an injury. The next year, he was traded to the California Angels.
Although in his late 30s by this time, Winfield was still a productive hitter. In 1992, he signed with the Toronto Blue Jays as their designated hitter, and batted .290 with 26 homers and 108 RBI. The Blue Jays won the pennant and gave Winfield a shot at redemption in the World Series. In Game 6 of the Series, he delivered with a game-winning two-run double in the 11th inning to win the World Championship for Toronto.
"Now it's on to May, and you know about me and May." --Winfield's comment after setting an American League record for RBI in April, 1988.
"I am truly sorry that a fowl of Canada is no longer with us." --Spoken to the press after being released following the 1983 bird-killing incident.