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Pinstripe Alley Top 100 Yankees: #35 Dave Winfield

The superstar’s mix of on-field performance and off-field chaos was a defining piece of the ‘80s.

Sports Contributor Archive 2018

Name: David Mark Winfield
Position: Right field
Born: October 3, 1951
Yankee years: 1981-90
Primary numbers: 31
Yankee statistics: 1,172 G, 5,021 PA, 1,300 H, 205 HR, 76 SB, .290/.356/.495, 134 OPS+. 27.1 rWAR, 26.5 fWAR


Pretty famously, baseball is a sport where players with all kinds of body types can succeed. Jose Altuve and Aaron Judge can tangle atop AL MVP ballots, Esteury Ruiz and Kyle Schwarber can be leadoff hitters despite 60 pounds of difference in their list weights. As we get closer to the top of this list, we’re going to see guys that don’t, as Dusty Rhodes put it, look like the athlete of the day — hello Babe Ruth.

Dave Winfield was not that guy. Perhaps the best pure athlete to ever play for the Yankees, Winfield was drafted by four major sports leagues, and the story of the game should be thankful he chose baseball. A star of the oft-maligned 1980s Yankees, Winfield still hit more home runs than Robinson Canó, drove in more than Tino Martinez, and scored more runs than Paul O’Neill. His on-field accomplishments came in parallel with a decade-long war with the owner of his team. He also killed a seagull in the middle of a game.

Minnesota Standout

Living with their single mother in St. Paul Minnesota’s historically black Rondo neighborhood, Dave and his brother Stephen were truly raised by a village. Mother Arlene was surrounded by a network of siblings who could pinch hit to watch the boys for a night, but perhaps the real work of keeping the boys busy was done by the Minnesota public school system.

By the time Winfield entered Saint Paul Central for high school, he was already honing his skills at baseball in the summer, and hockey in the winter — a tried and true approach to athletics in Minny. Dave put down the skates and took up a pair of Converse in high school, as his natural size made him a focal point of St. Paul Central basketball’s starting five. Earning all-state honors in both baseball and basketball, after graduation Winfield was drafted, for the first of many times, in the 40th round by the Baltimore Orioles.

Passing up that opportunity for a full-ride scholarship at the University of Minnesota, Dave continued his two-sport success for the Golden Gophers. In his junior year, making his way into the basketball starting lineup through sheer force of will and rebounding, the Gophers captured their first Big Ten championship in 53 seasons, and a year later, with a 2.74 ERA and .385 average, Winfield was an All-American on the diamond.

Dave Winfield Plays Basketball In College
A familiar No. 31.

It wasn’t all up and to the right for Winny in college though. After a promising freshman year he and a friend were arrested for stealing a pair of snow blowers, and after pleading to felony robbery received a three-year suspended sentence. In January of 1972, during a contentious B10 showdown with Ohio State, Winfield left the bench to join an on-court brawl after a particularly rough foul. While he wasn’t punished for that infraction, it was clear by the time college was wrapping up that Dave Winfield was a supremely talented athlete, albeit one with a bit of a chip on his shoulder.

Cue the 1973 College World Series, with Winfield the ace of the Big Ten champion Gophers. He kicked off the tourney with a complete game, 14-strikeout shutout over Oklahoma and faced down the USC Trojans on the final day of the bracket. After more than 140 pitches, Big Dave was staked to a 7-0 lead, had allowed just a single hit against 15 Ks in eight innings, and was trusted with delivering a second CGSO. By this point, Minny’s ace was gassed, allowing a pair of runs to open the ninth before being moved to left field, just in time to watch the relief corps blow the whole game. Minnesota lost 8-7, finishing third in the tournament — but Dave Winfield walked away with MVP honors.

Enter the draft circus.

The Padres made Winfield the fourth overall pick in the 1973 draft, while the Atlanta Hawks and Utah Stars picked him in the fifth and sixth rounds of the NBA and ABA drafts respectively. The Minnesota Vikings had selected Winfield in the 17th and final round of the NFL draft back in January, despite him never playing a snap of college football. While Winny must have loved the Golden Gophers, he must have hated all the drawn out winters, seeing as he went ahead with an MLB career and accepted a $15,000 signing bonus to join San Diego.

Straight to the Show

We’re in a time when prospects can move through systems pretty quickly. Alex Bregman and Dansby Swanson were polished college bats who went 1-2 in the 2015 MLB Draft, making it to The Show in a little over a full calendar year. Dave Winfield put that to shame, being promoted directly to the majors after signing, going directly from Minneapolis to playing 56 games in the majors in 1973. Since Winfield, only five position players have copied that trajectory.

San Diego Padres v New York Mets

Despite his pitching prowess, MLB teams saw Winfield as a slugging outfielder, never hurling in the majors and immediately being made the starting right fielder for the Padres. He handled himself well in those 56 games, being league average with the bat which in and of itself is an accomplishment given his spring and early summer.

Never a powerhouse in the NL West, the Padres finished over .500 just once during Winfield’s formative years, including 1977 when the 25-year-old outfielder finally broke out. An All-Star for the first time, he also had his first year of scoring more than 100 runs and posting a plus-.800 OPS for a 69-win Padres squad. That All-Star Game was played at Yankee Stadium, perhaps giving the still-relatively-new Yankee owner George Steinbrenner his first in-person look at the man he would torment for nearly a decade.

An All-Star each of the next two years, Winfield began to be seen as one of the game’s most feared bats in spite of his club’s struggles for relevance. He was named the Padres’ captain in 1978 as he continued to demonstrate his sensational talent.

The 1979 campaign would be the high-water mark of Winfield’s career, as belted 34 bombs and led the NL in RBI, OPS+, intentional walks, and both major WAR calculations. It was his second straight year of 20+ IBBs, a symptom not just of how scared opposing pitchers were to face him, but also of how punchless the rest of the Dads’ lineup was. Winfield was now one of the best hitters in the game, but he had become the guy you don’t let beat you. That ‘79 Padres team would score just 603 runs, and 118 of them — 19.5 percent!!!! — were driven in by the third-place MVP finisher.

Headed into the 1980 season, Winny was at a crossroads. A contentious extension signed ahead of that breakout 1977 campaign, along with growing frustration at the club’s inability to improve, signaled that the star was looking for a way out of San Diego entering his final season under contract. Never one to shy away from confrontation, Winfield addressed the gap between his accomplishments and the team’s bluntly.

Playing all 162 games in ‘80, it became clear to some that Winfield’s frustrations were both affecting his on-field play — his OPS dropped almost 140 points — and his general attitude, boiling over in a brawl with legendary hands-thrower Nolan Ryan.

As the 73-win season wound down, it was clear that Winfield’s time as a Padre was over. A second consecutive Gold Glove and fourth straight All-Star appearance would close the book on his tenure in Southern California, as the bright lights of New York beckoned.

Ten Years in Hell

On the surface, this should have been a perfect match. The Yankees were looking for an on-the-fly retool after a stunning 1980 playoff sweep against the Royals, flush with cash as Steinbrenner began to flex his muscles following a turnaround of the franchise’s fortunes. Dave Winfield was looking for a team that was ready to win, and one that could handle his personality. Ten years, $23 million was the price for Winfield’s services, the richest contract in baseball history to that point.

Before the ink was dry on the deal, there was drama. Steinbrenner, who prided himself on his ability to negotiate his own agreements, either didn’t read or didn’t understand a cost of living clause in the contract, one that added an additional $7 million dollars to Winny’s compensation.

Agent Al Frohman, upon learning how surprised (read: spitting mad) The Boss was at the inclusion of such a clause, vaguely threatened the owner of baseball’s premier franchise:

“If he ever touches a hair of my boy’s head … I’ll blow the lid. I’ve got stuff on George that if it ever came out, he would be in big trouble. It’s very easy to be friends with George if you have blackmail on him.”

All of this occurred before Winfield took a swing at the Stadium. Steinbrenner was the type to hold grudges only relative to the player’s performance, and in a strike-shortened season, Big Dave played in 105 of the Yankees’ 107 games, taking home another All-Star appearance and a Silver Slugger award in his debut turn with the Yankees.

In the first ever ALDS, Winfield hit .350 to pace the club over the Brewers, but after dusting Billy Martin’s Athletics in the Championship Series, he recorded just one base hit in the World Series loss against the Dodgers.

Now that the Silver Slugger was an annual award, it seemed you could pencil Winfield in for an All-Star selection, and both the league’s fielding and batting awards for the position. From 1979-85, Big Dave played in the Midsummer Classic each year, took home six Gold Gloves, and won the hitting counterpart five straight seasons in the Bronx. Despite being one of the top hitters in the game, with a fearsome swing and the consistency that fans (especially a certain future captain) yearn for, the Yankees didn’t make the playoffs again in his tenure.

In the Year of Three Managers, 1982, Winfield hit a career-high 37 home runs, and the perpetual low-simmering conflict between the outfielder and the owner seemed to reach its coolest point. With perpetual managerial changes and a playoff system unfriendly to the good-but-not-great, or great-but-not-the-best Yankees, it seemed the least of the team’s problems was their hulking slugger.

The ‘83 season was another typically excellent run for Winfield, although with yet another season missing the playoffs, the big story came in Toronto in August, when Dave’s throw into the ball boy in the mid-fifth struck a seagull in the base of the skull, and the bird dropped dead. Jays fans immediately began to heckle and lob objects at the Yankee outfield, and on-field Constable Wayne Hartery decided to arrest Winfield following the game.

Charged with “unnecessary suffering of an animal”, Winfield was booked on $500 bond, posted by Toronto GM Pat Gillick allowing the Yank to return to the team hotel.

The next day, the Crown Attorney assigned to the case found there was no evidence showing criminal intent, and although Winfield was booed mercilessly for almost ten years after the fact by Jays fans, charges were dismissed.

By 1984, that long simmering tension between player and owner began to bubble over again, as Steinbrenner began open attempts to get Winfield off his team even as Winny and captain Don Mattingly began a chase for the ages, hunting down a batting title that was decided by 0.003 points. Finishing the year at .340, Winfield watched Donnie Baseball collect four hits in the final game of the year against Detroit — with a rousing standing ovation in each plate appearance. The Hit Man ended the year at .343, and while the two stars walked off the field embracing each other, the positive vibes were skin-deep.

Winfield began to resent the overt favoritism shown to Mattingly. Don was the hometown player, so fans gravitating toward that was nothing new — Dave even compared himself to the reaction Roger Maris would get as he bypassed Mickey Mantle back in ‘61. But the greater support Mattingly received from his teammates and the public backing by Steinbrenner had Winfield questioning whether his Blackness had something to do with the whole situation.

Ozzie Smith, when Big Dave left San Diego, remarked that the towering outfielder carried an air of holier-than-thou-ness, so again we can’t really be sure how much of this resentment was borne out of real grievances or Winfield’s pride. For what it’s worth, the Yankee cleanup hitter always insisted that his issues had nothing to do with Mattingly personally. We do know that that great, historic 1984 chase was probably the last, best moment for Dave Winfield in pinstripes.

All-Out War

“Where is Reggie Jackson? We need a Mr. October or a Mr. September. Winfield is Mr. May.”

Dave Winfield had a 120 wRC+ in the first half of 1985, and a 114 in the second. Now yes, that is technically a decline in performance, but nothing so striking as to merit a name that stuck so well. Debate rages about whether Steinbrenner uttered the above quote after the ‘81 World Series failure or after a particularly ugly loss down the stretch of ‘85 to the division-leading Blue Jays, though New York Times reporter Dave Anderson went to his grave insisting it came in the latter year.

And that was the crux of Steinbrenner’s frustration, not just with Winfield but with Ken Griffey and Don Baylor. His “big money players” weren’t playing like such, in his eyes. That those three players, specifically named in Anderson’s NYT piece, were all Black should not escape notice. Baylor would be dealt to Boston before the 1986 season, and Griffey would be sent to Atlanta in the middle of the same year, but Winfield’s contract made any kind of trade tricky. George began to instruct Lou Piniella to bench or platoon his nominal cleanup hitter.

Payments then were withheld from the Yankees to the Dave Winfield Foundation, a clause deliberately inserted into that 10-year, $23 million contract to follow a precedent set in Winfield’s San Diego days. After receiving a court order to resume payments, advised by the paragon of legal ethics that was Roy Cohn — himself dying while denying his AIDS diagnosis and being disbarred — Steinbrenner sued to remove Dave from the board of the foundation, claiming poor financial management and failure to deliver on specified objectives.

Sports Contributor Archive 2019 Photo by Ron Vesely/MLB Photos via Getty Images

All Winfield did on the field during these two most toxic seasons was blast 51 home runs and drive in 201 runs.

Enter Howie Spira.

A bookie with low level Mob ties, Spira and Winfield had been moving in similar circles since 1981, with Spira acting as a kind of moronic information broker. Approaching Winfield in 1987 claiming to have damning information on The Boss and being turned down, Spira went to Steinbrenner with a similar offer. $40,000 changed hands, and leaks began to spread that Dave Winfield was betting on baseball.

Reeling from the Pete Rose affair, the MLB commissioner’s office began a full investigation after Spira finally, publicly levelled his accusation. Said investigation was an unmitigated disaster for George Steinbrenner, as it not only found no evidence Winfield was gambling, but that the Polestar of Human Evil Cohn’s suggestion of financial impropriety at the Winfield Foundation was a lie as well. Steinbrenner was forced to give up control of the team, accepting a ban that wasn’t lifted until 1993.

Winfield was vindicated but embroiled in a toxifying and rapidly disintegrating relationship with the Yankees, even one nominally Steinbrenner-less. After missing the ‘89 season with a back injury, he was left off the All-Star ballot in the 1990 season, the second-to-last straw before a May 11th deal to the Angels — the final one being a quarter-million dollar fine for tampering with the Angels/Winfield relationship even after the trade was completed.

No Longer Mr. May

Whatever you think of Dave Winfield — arrogant, hard-nosed, talented, philanthropic — his story climaxed in a Blue Jays uniform. Signing with Toronto ahead of the 1992 season, he was one of several veteran pieces added to a talented core in hopes of capturing a franchise’s elusive world championship.

At 40, Winny notched a 140 wRC+ while striking out almost exactly as much as he walked and finishing fifth in AL MVP voting. As George Steinbrenner was so fond of noting though, it was what you did in October that counted. Whether Winfield was carrying some lingering hate for The Boss entering that season’s playoff run we’ll never know, but he finally had his baseball moment.

That double in that reel above ended up winning the whole damn Series for Toronto, and Winfield was once again vindicated, this time on the sport’s biggest stage. You’ll still find some old school Jays fans referring to him as Mr. Jay, despite just one glorious year north of the border.

Heading home to Minnesota for the ‘93 season off the high of the World Series, Dave Winfield solidified his Hall of Fame credentials in front of the MSP faithful with his 3,000th career hit.

Two years later, Winfield walked off the diamond for the last time. He had joined the offensive powerhouse in Cleveland in time for their outstanding 1995 season, but a busted-up shoulder limited his play and he was inactive for their postseason run. Winfield retired with sterling numbers: 3,110 hits, 540 doubles, 465 homers, and a 130 OPS+ across 22 years.

As Steinbrenner began his return to Yankee operations, and the Yankees themselves returned to baseball Providence, The Boss privately attempted to reconcile his relationship with his one-time superstar. How do you forgive a man that made your life hellish for a decade, who within a year of giving you the largest contract in sports seemed determined to root you from the roster, in legal ways and others?

Perhaps age sands down all our sharper edges, as Winfield admitted in his Hall of Fame induction speech that both men had grown and grown closer.

Although Winfield still did go into the Hall with a Padres cap, after his induction the relationship had warmed enough that August 18, 2001 was Dave Winfield Day at Yankee Stadium. The club stopped short of retiring his No. 31, but started to freshen up ties between the two parties; he later appeared at a few Old-Timers’ Days, as well as events closing The House That Ruth Built in 2008.

Dave Winfield was arguably the best pure athlete to ever step on a baseball diamond, and his career accomplishments speak for themselves. He tallied 3,110 hits, was a key figure in the history of three franchises while remaining a hometown hero for a fourth, and he became a first-ballot Hall of Famer in 2001. Yet it was his personality and how it clashed or paralleled with the biggest names in the sport that perhaps best define his legacy. He was the most consistent, best year-in-and-out player in a lost Bronx decade, but the chaos that surrounded him may leave his legacy a slot below the type that The Boss specifically would call a “true Yankee” ... even if the totality of his career dwarfs many of them.

Dave Winfield, former New York Yankees player, waves to the Photo by Jin Lee/Bloomberg via Getty Images

Staff rank: 36
Community rank: 30
Stats rank: 49
2013 rank: 42


Anderson, Dave, “IMPATIENCE IN THE RUINS”, The New York Times, Sept 16, 1985.

Baseball Reference

Dean, Michelle, “A mentor in shamelessness: the man who taught Trump the power of publicity,” The Guardian, Apr 20, 2016.



Fung, Adrian “August 4, 1983: Dave Winfield’s errant throw accidentally kills seagull in Toronto”, SABR.

Madden, Bill. Steinbrenner: The Last Lion of Baseball. New York: HarperCollins, 2010.

Reilly, Rick. “I Feel a Whole Lot Better Now; Dave Winfield’s 20-Year Baseball Career, Often Touched by Trouble and Trauma, Has Taken a Happy Turn in Toronto,” Sports Illustrated, June 29, 1992.

SABR Bio, Doug Skipper

“Yanks Must Pay $225,000 For Winfield Tampering,” The New York Times, July 6, 1990.

Previously on the Top 100

36. Reggie Jackson
Full list to date