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14Rachel Uchitel

Here’s someone who apparently has a knack for landing famous boyfriends. Though, for at least one, I don’t know if it warrants the label “boyfriend,” as she was one of the many women Tiger Woods was shagging in the rough, too. But, she wound up shagging fly balls with Derek

Jeter too, back around 2008. She was certainly meeting the requisite level of hotness that appeared to be The Captain’s standard, as she was up for a spread in Playboy, after all. Now, while that would seem plenty attractive for ninety nine percent of the men in America, clearly she wasn’t hot enough for Jeter (or, you know, they had other compatibility issues and it wasn’t at all about looks). But, as with every other one of his exes, surely there’s a wee bit of disappointment there. I’d wager she dislikes him at least a little bit and who could blame her.

Next 13 Derek Jeter’s Neighbors

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