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George Steinbrenner (1930–2010)

Why I’m actually going to miss that meddlesome pain in the ass.

Writing back and forth with a fellow Yankee fan just after the news broke about George Steinbrenner’s death, I was surprised how touched we were. Like Yankee fans generally, we had lambasted Steinbrenner for decades. He was a meddlesome pain in the ass. He brought an obsessively willful football coach’s mentality to a subtle sport played over a very long season. And his strange emotional twists and turns with other troubled men, above all his many-time manager, Billy Martin, played havoc with everyone’s psyches. Indeed, Steinbrenner was capable of truly despicable behavior.

Steinbrenner hit his lowest, in my book, at the end of the 1980s, when he paid $40,000 to a small-time Bronx grifter named Howie Spira to dig up dirt on Yankee superstar outfielder Dave Winfield. Winfield had outraged The Boss first by outfoxing him at the negotiating table to the tune of millions, then by failing (as Steinbrenner saw it) to lead the Yankees to a World Championship. Spira wound up serving 22 months in a federal prison for extortion. Baseball commissioner Fay Vincent banned Steinbrenner in 1990 from any day-to-day involvement with the team for 30 months. Winfield, who won a World Series ring with the Toronto Blue Jays in 1992, is now in the Hall of Fame.

But baseball, spiritually, is Sophoclean, so I’d argue that Steinbrenner’s hubris and disgrace in the Spira affair helped build the great Yankee teams of the mid-1990s and after. Before his suspension, Steinbrenner ordered his minions to stock up on talented but past-their-prime veterans like Ken Phelps and Rick Rhoden—and they assembled a second-division club that finished thirteen games below .500 the year of Stenbrenner’s suspension. But with Steinbrenner temporarily gone thanks to the Spira episode, general manager Gene “Stick” Michael had a free hand to concentrate on patiently developing younger talent. Michael’s strategy paid off in 1995, with the major-league debuts of each of the so-called “core four” of durable superstars—Derek Jeter, Mariano Rivera, Andy Pettitte, and Jorge Posada—who helped win the team championship after championship, and have led the Yanks to the best record in baseball as of this year’s All-Star break. That was Michael’s doing at least as much as if not more than it was Steinbrenner’s.

Yet there was another Steinbrenner, or, better, a later Steinbrenner, whose tragic flaws ceased to be quite so tragic. It did not take too much exposure to his public personality to see that the man’s imperiousness was driven by a fear of losing, a horror of disgrace, which, if it did not compensate for his sins, somehow rendered him less hateful, or at least more human (and also more of a baseball fan, like the rest of us) than his sadist caricature. And over the past 15 years, with the core of a mighty team in place and unmoving, his fears and panicky habits seemed to abate, his decision-making sharpened, his personality mellowed—and even his vices suddenly looked a little virtuous. He approved some excellent executive hires, of Brian Cashman as general manager and, above all, as team manager, Joe Torre, that brilliant handler of players and even more brilliant shock absorber with regard to management. Steinbrenner’s taste for experienced free-agent talent brought the likes of Tino Martinez and Paul O’Neill to Yankee Stadium. The same penchant for sentimental loyalty and reclamation that operated destructively with Billy Martin drew Steinbrenner to distressed heroes such as Darryl Strawberry and Dwight Gooden, who in turn made stellar contributions to the return of Yankee glory.

By the turn of the century, Steinbrenner had become a cultural icon, an exemplar of blustering authority. Once that icon became a comic figure, above all in Larry David’s back-to-the-camera performances of Steinbrenner on Seinfeld, his reputation was bound to soften. Sometimes, anyway, The Boss was not just in on the joke, he actually seemed to enjoy it. To the fictive extended family that is hardcore Yankee fandom, he became the grumpy old guy who still ran the show, but wasn’t as infuriating as before—especially because the show on the field, which is really all that matters, had become so wonderful.

Steinbrenner could still be offensive, not least at his worst moments during the protracted negotiations with political officials that led to the building of the new Yankee Stadium. Students of the ethics and political economy of Major League Baseball may discover fault in him for aiding and abetting in the scandals and ugly changes that have beset the sport, including stratospheric ticket prices and the blind eye that management turned for so long to illegal steroid use by the players. But for all of that, the Yankees remain in the Bronx, the team has enjoyed a run over the last 15 years that rivals any in its history, and it’s been a long time since Yankee fans were deeply embarrassed by the man who owned the team.

When the legendary public address announcer, Bob Sheppard, died a few days ago, a strong touch of grace departed, a spirit of correctness and class that generations of immigrants inherited from a bygone Knickerbocker New York. George M. Steinbrenner was, by contrast, a piece of work, too often, early on, a rough piece of work. But almost in spite of himself he became our piece of work, and the Yankees’ piece of work, when all along he thought it was the other way around.

Sean Wilentz is the author of Bob Dylan in America, which Doubleday will publish in September.  

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