Did He Or Didn’t He? New Documentary On Derek Jeter Examines Urban Legend He Gave Gift Baskets And Memorabilia To Dates.

FILE - Derek Jeter, CEO of the Miami Marlins, speaks with the news media before a baseball game against the Philadelphia Phillies, Saturday, Oct. 2, 2021, in Miami. Derek Jeter announced a surprise departure from the Miami Marlins Monday, Feb. 28, 2022.(AP Photo/Lynne Sladky, File)

Poor Derek Jeter. The man who loves staying under the radar has to live with the fact that a new documentary is out called “The Captain,” and that means he has to answer all kinds of questions about things that either did or did not happen back in the day when he was a star player for the New York Yankees. 

Jeter prided himself on being dull, but there was one story about the notorious serial dater who was considered one of the most eligible bachelors in the Big Apple that he can’t shake. 

Did he actually give gift baskets his dates could help themselves to as they were departing his high-rise condo the morning after?  You know, like a gift bag at an awards show, loaded with goodies and articles of appreciation. 

Jeter says “no” in the slow-moving ESPN documentary.  

Someone else says “yes.”  Her name is Emily Smith, the editor for the New York Post Page Six, and according to her, a trusted source from the 2000s told her about receiving gift baskets and memorabilia after leaving his pad.  Smith even said she saw photos of the goods but ultimately didn’t publish those photos. 

Isn’t this great? Allegedly, a future hall of fame had a nice little gift bag with what, scented candles, bath balms, and a used pair of batting gloves? 

Here’s a line from Smith in the doc.

“It’s difficult because Derek wouldn’t comment on it, and of course the team wouldn’t comment.”

Here’s one of Jeter’s true talents; he could be so dull, uninteresting, and blah as an interview subject, but he was a magnetic and charismatic force at night, scoring dates with scores of lovely ladies during his nearly two-decade run as a single man. 

Smith also said that just because one of Jeter’s departing guests may have allegedly received a nice token of his appreciation, it does not mean anything romantic happened. 

They could have been watching game film together to tweak his batting stance.  Or analyzing launch angles of an upcoming pitcher. 

Join the conversation!

We have no tolerance for comments containing violence, racism, profanity, vulgarity, doxing, or discourteous behavior. If a comment is spam, instead of replying to it please hover over that comment, click the ∨ icon, and mark it as spam. Thank you for partnering with us to maintain fruitful conversation.