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Derek Jeter’s Lady-Killing Past Before Hannah Davis

The Yankees legend is rumored to be getting engaged to model Hannah Davis—just like he was rumored to be getting married to Minka Kelly.

10.28.15 3:39 PM ET

Derek Jeter is rumored to be engaged to Sports Illustrated model Hannah Davis, who is 16 years his junior. Before anyone believes she’s tamed him, remember that Minka Kelly was also Jeter’s rumored fiancée in 2011.

There are a lot of women who wishes they could even be mentioned as rumored fiancée of Derek Jeter, though.

It’s hard to think of another baseball player in recent memory whose batting stance made so many fans weak at the knees. As the Keith Olbermanns of the world have made abundantly clear in their vitriolic responses to the outpouring of Jeter tributes, Mr. November was neither the best hitter nor fielder during his 20 years in baseball. But in addition to being a really damn good hitter and making some jaw-droppingly stunning plays that have earned him a guaranteed spot in Cooperstown, Jeter charmed the New York sports media, whose glare ranges from irritating to debilitating (hey there, A-Rod). And, as the Post and the Daily News started taking notice of the 22-year-old Kalamazoo native in 1996 (the year he’d cruise to American League Rookie of the Year), the Big Apple found its new celebrity crush. Not since Broadway Joe had the women of the five boroughs gone into Beatles-on-The-Ed-Sullivan-Show ecstatics for one of its athletes.

During the last 20 seasons, rare was the game at Yankee Stadium that did not feature female fans of all ages declaring their sexual availability to the Captain. On Opening Day 2002, Christie Lee Wilcox earned herself a criminal trespass charge when she jumped out of the third-base stands to rush to the shortstop with a piece of paper with her phone number on it. She also earned the scorn of every tri-state area woman who wished she had the balls to come within arm’s reach of the hot shortstop. Hell, even Tom Brady has admitted to man-crushing on Derek Jeter. That says a lot coming from a Boston bro–and one married to Gisele, no less.

Not that Jeter hasn't had Gisele-calibur ladies in his past. As mentioned above, he has racked up an impressive list of celebrity ladies. ESPN's SportsNation compiled a Derek Jeter dating diamond, and Mariah Carey and Jessica Alba were relegated to the outfield. 

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Few things are as devastating to a female New Yorker born in the late 1980s as discovering she’s too old to date Derek Jeter (because youth was the one thing stopping the Captain from us). Jeter’s rumored/reported dating history suggests that he’s a total playboy who seemingly discards inimitably hot women in the same manner the Yankees dump healthy, young prospects. Yet, while watching A-Rod go through Madonna, Cameron Diaz, and Kate Hudson added a faint layer of horndog to his overall reputation as a $252 million jerk-off, Jeter has managed to avoid the Lothario label. That Jeter has charmed denizens of Average Janes is actually more remarkable than his off-the-field catches–which, for the record, reportedly include a Victoria’s Secret angel, a Miss Universe, and the current Mrs. Justin Timberlake.

In fact, legions of fans are more than eager to earn their souvenir gift baskets, despite the less than savory sexual rumors about the Captain. Jeter recently denied that rumor that he gave one-night stands gift baskets of his own memorabiliaand once gave it to the same girl twiceto New York magazine. That one seemed a bit far-fetched anyways because, as author Chris Smith notes, “Even if Jeter were cheesy enough to have handed out souvenirs, he’s far too careful to have made that kind of mistake.”

Besides, the gift bag peccadillo is the least skeevy of Jeter’s alleged bedroom behavior. And even that rumor isn’t nearly as cringe-inducing as the Captain’s alleged habit of softly cheering himself on with a “Yeah, Jeets” when women are going down on his Louisville Slugger, so to speak. Olbermann even closed out his near-seven-minute anti-Jeter rant with a nod to the notorious rumor. In the canon of Yankees blowjob mythology, this tale may even be more legendary than Mickey Mantle’s proud—and very detailed—account of receiving “therapy” for a pulled groin beneath the rightfield bleachers.

So, why do we still crush on Jeter when it’s easy to disregard him as the Adam Levine of the MLB? There’s the obvious answer: He’s pretty easy on the eyes, and in a softer, crush-worthy way. Unlike the Babe, Jeter’s body never needed the pinstripes to flatter his form (he even looked good when he was “Derek Eater” in the 2012 offseason). But it was the subtle things like his trademark side-smile or his formal “Mr. Torre” ways that had us swooning. Also, as far as the iffy history of athletes hosting Saturday Night Live go, he did a more than decent job playing a groupie in drag and debating Seth Meyers about whether he sucked. Humor, blue eyes, and Midwestern politeness: What more could the ladies (and a good portion of the men) of New York want?

Mike Segar, Reuters / Landov

Derek Jeter and former flame Minka Kelly.

Of course, charming the public with intangibles is something that Jeter-haters have long hated about the shortstop. Critics have argued his legendary fielding plays–the flip, the dive–may look great on SportsCenter, but his acrobatics can’t mask the fact his fielding may have hurt the Yankees. Others have argued that he was never really that great, and the sports world has made a big fuss over nothing. While I would strongly disagree with both of these statements, I understand the frustration with the parade of goodbye tributes that have made 2014 into one giant Farewell Jeter tour.

I understand the ire, but I find the criticisms as unconvincing as the allegations that Jeter murmurs his own name during oral trysts. Critics tend to rely on straw man arguments claiming Jeter wasn’t the very best. So what? No one in the Hall of Fame was the very best at every hitting or fielding measurement all the time either. Neither Jeter nor the Yankees have ever proclaimed he was the greatest player of all time, let alone of the franchise.

So, why do the critics keep comparing Jeter to the extreme? Because he’s still beloved after 20 years, and they find that highly suspect. The negative assessments of Jeter’s prowess on the field or in the bedroom tend to operate from the same premise that he is overrated and coddled by the media and, therefore, the public; that underneath the Steinbrenner-approved crew cut and charmingly formal and quiet ways with the press lies a horny egomaniac who has been conning us for the past 20 years. It’s not that I don’t doubt that Jeter isn’t media-savvy. I just don’t buy the conspiracy theory: Why would Jeter be the one cunning exception that pulled the wool over reporters’ eyes to win undeserved good will? I don’t doubt Jeter became a national name, in part, because New York fell in love with him, but it’s not like he was slipping us Benjamins to do so.

Maybe we loved him harder than the hot-headed Paul O’Neill or the respectfully devout family man Mariano Rivera or the bored, apathetic teenager that is Robinson Cano. And maybe it wasn’t always for the most rational reasons, but rather the crack of his smile or his clutch-hitting moments that were on full display at his last game at Yankee Stadium. Love means never having to say you’re sorry... even if it leads to a gift basket.

Editor’s Note: This story was updated with news of Jeter’s rumored engagement to Hannah Davis.