According to sources cited by the Post, the 37-year-old Jeter is making headlines for sending home his one-night stands with gift baskets of autographed memorabilia. The ritual came to light when Jeter made the mistake of pulling the stunt twice on the same woman, a source told the newspaper.
"Derek has girls stay with him at his apartment in New York, and then he gets them a car to take them home the next day. Waiting in his car is a gift basket containing signed Jeter memorabilia, usually a signed baseball," a source told the Post.
"This summer, he ended up hooking up with a girl who he had hooked up with once before, but Jeter seemed to have forgotten about the first time and gave her the same identical parting gift, a gift basket with a signed Derek Jeter baseball.
"He basically gave her the same gift twice because he'd forgotten hooking up with her the first time!"
Jeter has been known to stay out of the spotlight when off the diamond as a way to protect his image and marketability. He prefers to host house parties with a tight group of friends, according to the Post.
"He normally doesn't go out with girls. He will have them come to his house. He'll have cocktail parties. His friends invite girls they think he'll be interested in. He's very shy," another source told the Post.
Still, that reportedly hasn't stopped Jeter from getting around.
"I know he's been dating multiple girls. He likes a hole in the wall, or he likes a place that his friends own. He's very cautious. He'll only go out on off nights," the Post's other source added.
"The girls go through the back-door entrance in the Trump World Tower to avoid the paparazzi. He broke up with Minka in the summer and is definitely over her. He is playing the field."
Parting gifts like the ones these sources are alleging in this case carry a heavy price tag. Signed Jeter items are known to be big sellers on the Internet, with an autographed baseball going for hundreds, even thousands of dollars.