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A Former Yankees Batboy Opens Up About Derek Jeter’s Taste In Women, A-Rod’s Tipping, And More

by Glenn Davis | 9:15 am, August 9th, 2011

Luis Castillo became a Yankees batboy in 1998, working with the teqam through 2005. That put him right in the middle of championships, disappointments, greats of the game, headcases, and generally left him with a lot of stories to tell. And somehow, he’s allowed to tell them. At the time Castillo worked for the team, Yankees batboys still didn’t have to sign confidentiality agreements, which seems to us like a rather enormous oversight, but oh well – Castillo’s taking advantage in the form of a new book, titled Clubhouse Confidential (note: this general idea has been done before, perhaps with fewer juicy details), and the New York Post recently printed a few excerpts. We read them. We enjoyed them. Here, for example, is how Castillo acquired his nickname with the team:

Opening Day 1998 is my first day on the job and I arrive at Yankee Stadium not knowing what to expect. Before long, a thin teenager with curly brown hair approached and introduced himself as Joe Lee. A former batboy for the Yankees, he was then a clubhouse assistant. After we shook hands, he said, “You know you can’t start working here without being named.”

Being named? I followed him back into the clubhouse, and the first player I met was Derek Jeter.

[...]

“That’s it!” Jeter said. “Your nickname is Squeegee . . . You look like a squeegee.” He smiled.

Jeter, apparently, was an easygoing jokester around the clubhouse who would greet everyone by saying, “How’re you doin’, biatches?” Combine that side of him with the workaday, serious consummate professional player, and one gets a sense of why Jeter’s looked upon so fondly. Oh, and as for when he was into a girl at a bar, Jeter had a system: his personal trainer would go up to the woman, say Jeter wanted to talk to them, and then the woman would leave to meet Jeter, who’d already left…all the better to avoid snooping tabloid reporters. What kinds of women did Jeter like?

His preference was for women who had a nice smile and personality.

Of course. Of course his tastes would be that wholesome. Frankly, it even sounds a little too Jeter to actually be Jeter, but hey – maybe that’s because Jeter’s just like that. In any case, all we can do re: stories that sound too good to be true is wait to see if anyone disputes any claims in the book (not that Jeter would have a reason to take issue with the assertion that he liked women with “a nice smile and personality”).

There are some other amusing details, too, like how Alex Rodriguez just had to increase the amount he tipped Castillo when he found out other players tipped more than he did, so he could tip the most. There’s the shocking revelation that George Steinbrenner was, believe it or not, paranoid, and easily trolled into believing there were giant conspiracies against him and the team. And, of course, Hideki Matsui’s ultimately unfulfilled vow before Game 7 of the 2004 ALCS, which the Red Sox won to complete a comeback from down 3-0 in that series. What did Matsui promise the Yankees would do that night?