The Winfield brothers honed their athletic skills in St. Paul's Oxford playground, where coach Bill Petersen was one of the first to take the young Winfield under his wing. It wasn't until his senior year in high school that Winfield grew into the formidable 6'6" tower of power he would become.
He earned a full scholarship to the University of Minnesota in 1969, where he starred in basketball and baseball for the Golden Gophers. His college basketball coach was a young Bill Musselman, who went on to serve as a head coach in the American Basketball Association and National Basketball Association and would later refer to Winfield as the best rebounder he ever had. Winfield's 1972 Minnesota team won a Big 10 basketball championship, the school's first in 53 years. During the 1972 season, he also was involved in a brawl when Minnesota played Ohio State.
Winfield also played for the Alaska Goldpanners for two seasons (1971-72) and was the MVP in 1972. Following college, Winfield was drafted by four teams in three different sports. The San Diego Padres selected him as an outfielder with the fourth overall pick in the MLB draft and both the Atlanta Hawks (NBA) and the Utah Stars (ABA) drafted him. And even though he never played college football, the Minnesota Vikings selected Winfield in the 17th round of the NFL draft. He is currently one of two players ever to be drafted by three professional sports (the other being Dave Logan).
For the next several years, he was an All-Star player in San Diego, gradually increasing his power and hits totals. He burst into stardom in , when he batted .308 with 34 home runs and 118 RBI, then played one more season with the Padres before becoming a free agent.
Winfield 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 in September 1985 by saying to New York Times writer Murray Chass, "Where is Reggie Jackson? We need a Mr. October or a Mr. September. Winfield is Mr. May." Many commentators, however, note that Winfield’s post-season doldrums were somewhat overstated when compared to those of his teammates. In the exciting 1981 American League Division Series, Winfield batted .350 with two doubles and a triple and made some important defensive plays helping the Yankees to victory over the Milwaukee Brewers. Four of his seven hits came in games won by the Yankees. Although his World Series performance was poor, the offense for the most part was inconsistent, and the team was also set back by key injuries to Reggie Jackson and Graig Nettles. Still, the Mr. May sobriquet lived with Winfield until he won the 1992 World Series with Toronto.
Steinbrenner regularly leaked insulting stories about Winfield to the press and often tried to trade him, but Winfield's later status as a 10-and-5 player (10 years in the majors, five years with a single team) meant he could not be traded without his consent. Winfield, however, did not let Steinbrenner's antics affect his play, as he hit 37 home runs in a spectacular season and in , he batted .340, second in the league to teammate Don Mattingly by .003 points in a memorable race for the batting title. He drove in 744 runs between 1982 and , won five (of his seven) Gold Glove Awards for his stellar outfield play, and was selected to play in the All-Star Game every season.
On August 4, , Winfield, while warming up before the fifth inning of a game at Toronto's Exhibition Stadium, accidentally killed a seagull with a thrown ball. He doffed his cap in mock sorrow. Fans responded by hurling obscenities and improvised missiles. After the game, he was brought to the Ontario Provincial Police station on charges of cruelty to animals and was forced to post a $500 bond before being released. Quipped Yankees manager Billy Martin, "It's the first time he's hit the cutoff man." The charges were dropped the following day. For years afterward Winfield's appearances in Toronto were greeted with loud choruses of boos, but he later became a fan favorite due to his outstanding play once he joined the Blue Jays.
In , Steinbrenner was suspended from running the Yankees for two years because of his connections to Howie Spira, a known gambler with Mafia connections, whom he had paid $40,000 for embarrassing information on Winfield. The year was no better than the year before for Winfield, who had sat out with a back injury. The next year, he was traded mid-season to the California Angels. Winfield won the 1990 MLB Comeback Player of the Year Award .
Winfield proved to be a lightning rod for the Blue Jays, providing leadership and experience as well as his potent bat. Winfield was a fan favorite, but also demanded fan participation. In August 1992 he made an impassioned plea to the fans during an interview for more crowd noise. The phrase "Winfield Wants Noise" became a popular slogan for the rest of the season, appearing on t-shirts, dolls, buttons, and signs.
The Blue Jays won the pennant, giving Winfield a shot at redemption for his previous late-season and post-season futility. In Game 6 of the World Series, he became "Mr. Jay" as he delivered the game-winning two-run double in the 11th inning off Atlanta's Charlie Leibrandt to win the World Championship for Toronto.
During the 1994 baseball strike, which began on August 12, Winfield was traded to the Cleveland Indians at the trade deadline on July 31 for a "player to be named later." The 1994 season was cancelled two weeks later, so Winfield did not play for the Indians that year and no player was ever named in exchange. To settle the trade, Cleveland and Minnesota executives went to dinner, with the Indians picking up the tab. This makes Winfield the only player in major league history to be traded for a dinner.
Winfield was again granted free agency in October but resigned with the Indians as spring training began in April . As MLB's oldest player in 1995, Winfield played in 46 games and hit .191 for Cleveland's first pennant winner in 41 years, but did not participate in the Indians' postseason.
He’s said he regrets a lot of things that happened. We’re fine now. Things have changed.
In , Winfield ranked number 94 on The Sporting News list of Baseball's Greatest Players, and was a nominee for the Major League Baseball All-Century Team.
On July 4, , Winfield was inducted into the College Baseball Hall of Fame in its inaugural class.
On June 5, , Major League Baseball held a special draft of the surviving Negro League players to acknowledge and rectify their exclusion from the major leagues on the basis of race. The idea of the special draft was conceived by Winfield. Each major league team drafted one player from the Negro Leagues.
Winfield currently serves as a vice president of the Padres.
Known as much for his philanthropic work, Winfield began giving back to the communities in which he played from the beginning of his professional athletic career. In 1973, his first year with the Padres, he began buying blocks of tickets to Padres games for families who couldn't afford to go to games, in a program known as "pavilions". Winfield then added health clinics to the equation, by partnering with San Diego's Scripps Clinic who had a mobile clinic which was brought into the stadium parking lot.
When Winfield played for the Toronto Blue Jays, he learned teammate David Wells was one of the "Winfield kids" in San Diego.
In his hometown of St. Paul, he began a scholarship program (which continues to this day). In 1977, he organized his efforts into an official 501(c)(3) charitable organization, known as the David M. Winfield Foundation for Underprivileged Youth, the first active athlete to do so.
As his salary increased and he partnered with more corporations, the programs expanded to include holiday dinner giveaways and national scholarships. In 1978, San Diego hosted the All-Star game, and Winfield bought his usual block of pavilion tickets. Winfield then went on a local radio station and inadvertently invited "all the kids of San Diego" to attend. The huge turnout resulted in the first open-practice of the All-Star game, which has been adopted by Major League Baseball and continues to this day.
When Winfield joined the New York Yankees, he set aside $4 million of his salary for the Winfield Foundation. The Foundation then partnered with Merck Pharmaceuticals and created an internationally acclaimed bilingual substance abuse prevention program called "Turn it Around".
The Foundation also became a bone of contention in Winfield's public feud with George Steinbrenner; Steinbrenner accused the Foundation of mishandling funds and often held back payments which resulted in long, costly court battles. Ironically, Steinbrenner was in fact holding back part of Winfield's salary; he wasn't actually making contributions to the Foundation. Ultimately, the Foundation was paid and the alleged improprieties proved unfounded.
This aspect of Winfield's career influenced many of MLB's players as much as his on-field play. Derek Jeter, who grew up idolizing Winfield, credits him for his own philanthropic endeavors. His own Turn2 Foundation has honored Winfield , and Winfield continues to help raise funds and awareness for Jeter's Foundation and for many other groups and causes throughout the country.