Before Aaron Judge and Giancarlo Stanton, Dave Winfield (along with Dave Parker) was the definitive “Holy (bleep) that guy is huge!” star. Although his Yankees tenure was clouded by a tumultuous relationship with George Steinbrenner, Winfield deserves to be remembered as a great Yankee who made those 80s teams memorable despite never winning a ring.
David Mark Winfield
Born: October 3, 1951 (St. Paul, MN)
Yankees tenure: 1981-1990
Winfield’s athletic abilities were already quite apparent in his youth.
He starred in both baseball and basketball in high school and college. Following his time at the University of Minnesota, he was drafted by teams from not one, not two, but three pro leagues — in addition to MLB’s Padres and the NBA’s Atlanta Hawks, the NFL’s Minnesota Vikings took a flier on Winfield even though he hadn’t played college football. Thankfully, the hulking phenom chose the diamond.
The Padres thrust Winfield into the fire, having him skip the minor leagues entirely and placing him on their major league roster. While he wasn’t exactly a star from the word go, he was a productive regular almost immediately, hitting .277/.331/.383 (106 wRC+) across 154 PAs in 1973 as a 21 year-old.
From there, Winfield continued to steadily improve, going from 1.9 WAR in ‘74, to 2.8 in ‘75, and 4.6 in ‘76. In 1977, he earned his first All-Star selection; he returned to the Midsummer Classic every year from then on until 1988. His pièces de résistance came in 1979, when he slashed .308/.395/.558 (161 wRC+) with 34 homers and a league-leading 118 RBI while winning a Gold Glove in right field. His 7.8 WAR paced the National League, even though he finished 3rd in MVP voting. Bet all the keyboard warriors were furi- oh right they didn’t exist back then.
All this was more than enough to catch the eye of George Steinbrenner, who was eager to add another ring after consecutive titles in ‘77 and ‘78. In December 1980, the Yankees made Winfield the richest player in baseball with a ten-year, $23 million contract. Winfield almost made the Boss’ dream come true in ‘81, posting a 139 wRC+ in the strike-shortened regular season before showing out on both sides of the ball in the ALDS and ALCS. Here’s the large baseball man robbing Tony Armas of a home run in ALCS Game 2:
However, the season ended on a sour note for Winfield and the Yankees. The Dodgers won the World Series in six games, and Winfield was limited to just one hit in 22 at bats. In a show of poor comedic timing, he asked for the ball after his lone hit, a single. Needless to say, this did not sit well with George Steinbrenner, and the two would become bitter enemies for the remainder of Winfield’s time in the Bronx.
The 1981 season would be the Yankees’ only postseason appearance during Winfield’s tenure. However, that was no fault of Winfield’s, who kept producing at a high level well into his thirties. Although modern defensive metrics suggest that his sterling defensive reputation at the time wasn’t wholly deserved, there is absolutely no doubt about the quality of his bat.
In terms of batting average, Winfield’s best year came in 1984, when he locked horns with a young Don Mattingly for the AL batting title. The teammates were tied going into the very last game of the season, but Mattingly won the title by going 4-for-5, raising his average to .343, while Winfield went 1-for-4, finishing the year at a .340 clip. Here’s a clip of him from that year showing not only his sheer strength, but the impressive plate coverage that allowed him to hit for such a high average:
On the other hand, saber-enthusiasts like me would point to 1988 as Winfield’s best season in pinstripes. That year, he slashed .322/.398/.530 for a 157 wRC+, the fourth-highest mark in the majors. What makes this even more impressive is that he did this at 36 years old. To put this into context, Giancarlo Stanton was in his age-35 season when he surprised us all by posting a 157 wRC+ in 77 games last year. Now imagine him being just as good this year, except over a full season. Can you? I certainly can’t. Among all qualified seasons by batters aged 36 or above since 1947, Winfield’s 1988 ranks 19th, tied with 1971 Willie Mays and 2001 Edgar Martinez.
All told, in his time as a Yankee, Winfield hit .290/.356/.495 with 205 homers and 818 RBI. No matter how you slice it, he was worth every penny of his contract. And yet, George Steinbrenner, famously afflicted with a severe case of “what have you done for me lately”-brain, made it his personal mission to antagonize Winfield at every turn.
In 1985, after the Yankees faded late in the season and ceded the division lead to the Toronto Blue Jays, the cantankerous owner derided Winfield in the papers, saying, “Where is Reggie Jackson? We need a Mr. October or a Mr. September. Winfield is Mr. May.” In 1987, Steinbrenner began to withhold payments owed to Winfield to be donated to the Winfield Foundation, founded in 1977 to provide relief and opportunities to struggling families in his hometown of St. Paul. Steinbrenner accused Winfield of misappropriating funds for personal gain, circulating unfounded reports in the media in an attempt to undermine the star player’s credibility.
Ultimately, Steinbrenner would ruin himself in his quest to tarnish Winfield’s name. The Yankees owner made a deal with gambler and alleged Mafia associate Howie Spira, paying him $40,000 in exchange to dig up dirt on Winfield. Spira publicly accused Winfield of betting on baseball, and commissioner Fay Vincent launched an investigation. However, no evidence was found of Winfield ever betting on baseball; what was uncovered was Steinbrenner’s clandestine deal with Spira. Vincent ordered Steinbrenner to resign as general partner of the Yankees and banned him from team operations for three years, and that was that.
At that point, Winfield had had more than enough. In May 1990, he waived his no-trade clause and accepted a trade to the California Angels, where he would play the following season as well. In 1992, at 40 years of age, Winfield played a crucial role on the championship-winning Blue Jays, hitting 26 homers and driving in 108 in the regular season, and coming up with the decisive blow in Game 6 of the World Series, an 11th-inning, two-run double. So much for the “Mr. May” moniker!
After three more years in the majors, two with his hometown Twins and one final year with Cleveland, Winfield called it quits. His career numbers are truly staggering; 465 homers, 3110 hits, and a .283/.353/.475 line over 23 seasons. In 2001, in his first year of eligibility, he was elected to the Hall of Fame.
Dave Winfield was a truly elite player who shone brightly in the Bronx. It’s a shame that he only had one chance to play in the postseason as a Yankee, but that shouldn’t cloud our appraisal of what he contributed to this franchise. For the better part of a decade, Winfield provided Yankee fans with top-level play, even as his teams could not quite reach October. He deserves to be remembered as one of the Yankees’ best free agent signings of all time, and just simply as a Yankees great.













