[Enjoy this guest post by frequent contributor Trevor Seigler! – Ed.]

I think Steinbrenner could have pulled this look off.

To say that George Steinbrenner was the owner of the New York Yankees would be like saying Michael Jackson was a pop singer; it’s technically true, but both men were so much more. Both were driven by the desire to be loved by their fathers (a desire that went unrealized), both reached such a level of omnipresence on the pop-culture landscape that you couldn’t hope to be neutral about them, and both went through money like W.C. Fields in a liquor store. The Boss and the King of Pop were massive in terms of ego, but hidden beneath the bluster were small kids forever yearning for love.

You might think it’s crazy to compare Steinbrenner to Jacko, but both men, separated in death by a year, were contemporaries in terms of when they rose to the public spotlight. When George Steinbrenner bought the Yankees in 1973, promising to be a “hands off” owner, Michael Jackson was still the kid brother of the Jackson 5, taking baby steps towards his own solo career. I won’t belabor the MJ/Steinbrenner comparisons further except to say that both men experienced ecstatic highs and soul-crushing lows, somehow managing to remain in the public eye until the day each died.

George Steinbrenner, the New York institution for so many years, was an outsider; born and bred in the Midwest, a native son of Cleveland, Ohio. His father ran a shipping business, and that’s how George managed to make his money. He came to New York as an unknown entity, certainly a step up from the CBS-led management team that had led the Yankees to nearly a decade of futility, with only an occasional sniff at the postseason. By the time he relinquished control Lear-like to his two sons in 2007, the Yankees were restored as perennial winners or contenders with a domestic worth that made them the envy of sports teams everywhere. George III (he really was “George III”) was not the first team owner to transcend the confines of sports culture and make an imprint on the wider world, but he was most certainly the most colorful.

Steinbrenner, “the Boss,” was a quintessential New Yorker, brash and arrogant and convinced that he was always right (especially when he was frequently wrong). His tyrannical rule squashed the late Seventies renaissance in the Bronx and sent it into a decade-plus of irrelevance and mediocrity. He became the symbol of everything that was wrong with baseball in the free agency era, and he paid a huge price for that. Banned twice from baseball (once for contributing to Nixon’s appropriately named “CREEP” re-election effort, another time for trying to find dirt on Dave Winfield), he managed to come back and serve as the thorn in the side of whoever was the baseball commissioner that week. Even Joe Torre’s late-Nineties run of four championships wasn’t enough; eventually the longest-tenured of the Steinbrenner-era managers jumped ship for Los Angeles.

But more than just symbolizing the Yankees, Steinbrenner came to invade a wider cultural landscape. In the mid-Nineties, he became a recurring character on Seinfeld, hiring eternal schlemiel George Costanza and berating the hapless underling in vintage Steinbrenner-ese. The brash, outspoken and arrogant owner of the Seventies and Eighties became something of a comedic foil for the other George, a demented teddy bear who spouted off crazy lines (courtesy of the pen and voice of series creator Larry David) that didn’t seem out of place in Jerry Seinfeld’s bizarre world. Dorothy had pulled back the curtain on the Wizard, and it turned out that he wasn’t quite as awful as he had been made out to be (Steinbrenner’s former and current employees might have begged to differ).

In Seinfeld, Steinbrenner (reportedly a fan of the show) found a new public image, albeit one that he did little to contribute to. Sure, he had held a revolving door of managers over the years, including his legendary back-and-forth with Billy Martin. But he took ideas from Costanza and kept him on the Yankee payroll, earning laughs as he did so. King George had no clothes, so to speak, and was less hateful to the Yankee faithful as a result. It might be stretching it to say that Seinfeld gave the world a kinder, gentler George Steinbrenner, but it certainly helped make him warm and fuzzy for those yearning for the glory days once again.

When the Yankees returned to the fall classic for the first time in 1996, I found myself rooting for them even though I was a Braves fan. The last championship had occurred a year before I was born, and I grew up only knowing the Bronx Zoo, Mr. October, and the Martin/Steinbrenner soap opera only through hastily-written memoirs from former players. For eighteen years, the Yankees had stunk, and George was at the wheel, steering his own personal Titanic well past the surface of the ocean. Now, finally stepping back to let his executives run the show (though not completely hands-off), he could sit back and enjoy a Yankees victory. The meddling must have begun the day after the final Series-clinching game, considering how many has-beens were signed to the Yanks in the intervening years (Jose Canseco being the most obvious “what the hell were they thinking?” signing of all time). Buster Olney wrote about how Steinbrenner couldn’t leave well enough alone in The Last Night of the Yankee Dynasty, and it’s true that while the Yankees did win four championships they spent the next decade struggling to get back, all thanks to the return of King George.

Eventually, though, like an aged monarch whose vision was dimmed by the onset of madness or senility, Steinbrenner realized that he was not fit to run the team anymore. Giving his sons (Hal and Hank) the reins, George retired from public life, not quite Howard Hughes but similarly out of the harsh light of public scrutiny. And wouldn’t you know, the Yanks won last year with George nowhere near to screw it up.

But as is often the case with a person thrust into the public eye, the persona that he presented to the public was less than rounded. Steinbrenner may have been the “man you love to hate,” but he quietly donated millions to charity over the years out of his own pocket. For every fading-star role player he overpaid for, he balanced his checkbook by giving generously to those less fortunate than him. It may have been a publicity stunt, except for the fact that you never heard Steinbrenner boast about it. In public, he was blustery and bombastic, but in the days after his death former employees and others who benefited from his largesse helped construct a fuller portrait of a much more complicated man.

Love him or hate him (and as many Yankees fans could tell you, it was possible to experience both emotions within the same sentence), Steinbrenner was the last of a dying breed, the owner as the public face of the franchise. His extremely visible presence in the world of the Yankees and Major League Baseball left little doubt as to who was the biggest, the baddest, the one with the most cake. Unlike other colorful owners of an earlier era (O’Malley with the Dodgers, Finley with the A’s), Steinbrenner never moved his team from its urban confines, nor did he spare the checkbook if he thought he could win. And as he would tell you, he thought he could win every year. Whether he was good for baseball or not, it’s safe to say that the game will never be the same after he’s long gone. George Steinbrenner was the New York Yankees, and that will never change.