Twenty years ago to the day, I had my first dip into the turbulent waters that were George Steinbrenner’s mind. We at NEWSWEEK were doing a cover story on the infamous and famous owner of the New York Yankees—the “George” who no more needed a last name than a king of England. This was the blowhard the tabloids loved to call The Boss, and the team owner we would soon describe on our cover as “The Most Hated Man in Baseball” because of his brushes with the law, baseball management, players, media, and his own psyche. Back in 1990, Steinbrenner was under investigation by the baseball commissioner for paying $40,000 to a confessed gambler named Howard Spira—in an apparent attempt to dig up dirt on Dave Winfield, a player with whom Steinbrenner was feuding.
At the recommendation of his lawyers, Steinbrenner agreed to talk to me at length in his Tampa offices. I got the full ingratiating treatment: a signed baseball (alas, “George Steinbrenner,” not “Babe Ruth”), a navy-blue Yankees cap, a tour of his photo-filled headquarters, an arm around my shoulder, and an outpouring of compliments for the work of mine he professed to have read. The framed sign on George’s wall read: “If you ain’t got a hernia yet, you ain’t pulling your share of the load.” We discussed Lincoln (“You think Lincoln was popular?”), Manhattan cabbies (“They love me!”), Patton (a role model), and the history of Custer’s Last Stand that he was reading the night before. He understood none of the irony of the topic of the Little Bighorn, even though within weeks he would indeed get thrown out of baseball (again) for two years. A few days later, when I was back in New York, Steinbrenner called me to amend his answers about his current nightstand reading. He wanted me to know he was reading a great book about journalism and the Graham family—which just happened to own The Washington Post Company, which just happened to own NEWSWEEK.
I couldn’t help but laugh. “George,” I said, “are you kidding? Are you really calling me up to tell me that? I work for the Grahams.”
“I know that, but that’s not why I’m telling you!” he protested.
I laughed again and groaned. NEWSWEEK did the story, and Steinbrenner’s people called afterward to complain about the cover line, though I didn’t hear from George. While he was a bully and at times a self-caricature—not that removed from the unseen Yankees boss that George Costanza had on Seinfeld—he wasn’t stupid. In the 37 years he owned the team—until his death from a heart attack today at 80—he revolutionized baseball economics. His free-agent signings regularly didn’t pan out, but he made checkbook professional sports the norm—and a thousand millionaires thank him. His Yankees suffered through many awful years, but they still won 11 pennants and seven World Series; in recent years, in part as infirmity overcame him, he wisely let his baseball executives and his two sons control the team, avoiding reckless trades and being more patient with developing minor-league talent. Steinbrenner’s monomaniacal reign over the team produced the best line ever about him. John McMullen, onetime owner of the Houston Astros, used to own a tiny piece of the Yankees under George; asked to reflect on that experience, he said, “There’s nothing so limited as being a limited partner of George Steinbrenner.”
His impulsiveness and temper were less personal quirks than a leadership credo. For a stretch Steinbrenner fired (and rehired) managers so frequently it was, as George Costanza put it, like “a bodily function.” Office staff were terrified of him. Yet he could show grace and kindnesses—asking after ill family members, looking after former ballplayers with personal travails. And he had the ability to laugh at himself on occasion. He liked the Seinfeld bits and filmed several scenes for season seven (they wound up being cut). He hosted Saturday Night Live in 1990—in which a sketch depicted him, along with Saddam Hussein and Idi Amin, in a SlimFast ad parody. After his firings and rehirings of Billy Martin as manager in the 1970s, the two appeared in a Miller Lite “Tastes great/less filling” TV commercial. “You’re fired!” George says. “Oh, no, not again!” replies Martin. A few years ago, following a dustup with marquee shortstop Derek Jeter, the two did a self-mocking Visa commercial.
Steinbrenner loved the limelight, and the Yankee circus that he so long presided over hasn’t been the same since he retreated into old age. But unlike with other team owners and CEOs, it wasn’t the renown that Steinbrenner prized most. And it wasn’t the money, though the team he bought for a reported $10 million is now worth well over $1 billion. It was the winning that mattered—born of childhood or college slights, or a Cleveland inferiority complex. He had to win. When he didn’t, he would embarrass himself—and his customers—by apologizing to the “people of New York.” When he did, he would cry in public, endearing himself to many TV viewers at home who might be doing the same.
“Winning means everything,” the Boss told me in Tampa. “You show me a good loser—and I’ll show you a loser.” Many years ago, Steinbrenner was himself in the sulky in a series of celebrity harness races for charity. His first time on the practice track, he was told by an instructor (the legendary driver Billy Haughton) to stay safely on the outside. “I finished last,” Steinbrenner recalled. “So I go over to this girl who is standing there to get my horse. All the other grooms are laughing at her. And she says, ‘We bet when they run these races—and, of course, I got your horse. I lost $ 2.50.’ She was upset.”
That was too much for him to bear. “Screw this,” he said to himself. In the next heat, “I took my horse and fell in dead last. Then I pulled my horse and went for it, and just as I came to the finish line, right next to Billy, I went by him and just smiled. I won. The girl was collecting her money when I got back.”
That was George. During a World Series game at the old Yankee Stadium some years ago, I was in the press box and saw Steinbrenner in his box. I went over to say hello, identifying myself and NEWSWEEK. He sure remembered the NEWSWEEK cover years earlier. “ ‘Most hated man in baseball?’ ” he grumbled. I tap-danced a bit and offered that perhaps we had gone overboard. He smiled just a little, shook my hand, and said, “Nope, you were probably right.”
It’s hard not to like, just a little, somebody who could say that.