Former baseball star Derek Jeter has never been one to sit back and enjoy the quiet life. Since calling time on his playing days, Derek Jeter the businessman has come upon us. He’s also become chief executive officer and part owner of the Miami Marlins of Major League Baseball. Retirement from the field hasn’t resulted in a lack of activity on his part. But when it comes to other aspects of his life, things have quietened down for Derek on the dating front, or reached a crescendo depending on how it’s perceived!
Derek was something of a rockstar during his playing days. He had the clout, the personality, and this package seemed to attract a plethora of beautiful women to his side. At the height of his so-called powers, Derek was seen with stunning women, different beautiful celebrities every few months. He’s certainly got game when it comes to the dating front. His dating list reads like a who’s who of the acting profession and modelling industry! These are 8 women Derek Jeter has dated and another 8 that didn’t last very long.
16 DATED: Vanessa Minnillo
Today, Vanessa Minnillo’s happily married and is a mom of three kids. But back in the day, way back in 2003, she was dating Derek. The two didn’t have a stable relationship. She was finding her feet in the limelight and the on-again off-again relationship she was having with Derek didn’t really help.
15 DIDN’T LAST LONG: Tyra Banks
Derek and Tyra Banks allegedly got together, although these rumors are unsubstantiated. They were seen together quite a few times at different events which got the rumor mill whirring. Both were IMG clients at the time and sat together at a basketball game. Tyra has never spoken on the topic, but if anything did happen, it didn’t happen for long.
14 DATED: Lara Dutta
Things really took off in the year 2000 for Lara Dutta. She won the Miss Universe crown which propelled her into the limelight, brought her to the attention of Bollywood and Derek Jeter. The two became quite close and it wasn’t long before they started dating, a relationship which lasted about a year.
13 DIDN’T LAST LONG: Scarlett Johansson
Silver screen star Scarlett Johansson would be on many people’s lists when it comes to the world’s most beautiful women. If rumors are to be believed, in the early 2000s she was on Derek’s radar too. Although Scarlett has denied the rumors, the duo were spotted leaving a Christmas party together. Make your own minds up!
12 DATED: Mariah Carey
Some people love her, a lot of people hate her, most love to hate her. One thing’s for sure and that’s that there was certainly love between Derek and Mariah once upon a time. They dated in the mid-90s and it’s thought that Mariah was Derek’s first so-called celebrity girlfriend. She’s a trendsetter alright.
11 DIDN’T LAST LONG: Bridget Hall
Looking through his history with women, it’s clear to see that Derek either goes for actresses or models. Bridget Hall falls into the latter category. Bridget achieved massive amounts of fame when she graced the cover of Sports Illustrated Swimsuit issue in the early 2000s. She became an instant hit will millions and caught Derek’s eye as well.
10 DATED: Jordana Brewster
Due to the Fast Saga, Jordana Brewster became a hit in Hollywood and to millions around the world. Derek dated her before she reached the height of her fame. The duo were spotted on his 28th birthday and were seen out and about together a couple of times after that. It’s thought they dated for a few months, which seems to have been the standard dating period for Derek during that time.
9 DIDN’T LAST LONG: Gabrielle Union
After splitting with Jessica Biel, it was rumored that Derek started up a casual thing with superstar actress Gabrielle Union. It’s wasn’t hard for people to jump on the bandwagon and start speculating, although Gabrielle has denied the relationship, stating that if she was dating Derek, she’d hold a press conference and announce it to the world.
8 DATED: Joy Enriquez
A-Rod brought actress Joy Enriquez to a game in 2001. That proved to be a big mistake on his part. Although A-Rod’s generally done quite well when it comes to women, he’s no Derek, and doesn’t have his game. Joy took Derek’s fancy, evidently the feeling was mutual and they ended up going out.
7 DIDN’T LAST LONG: Jessica Alba
Ask guys who their dream woman would be and Jessica Alba would be at the top of a lot of people’s lists. The gorgeous actress is stunning in every which way. It’s clear to see why she drew Derek’s attention. They briefly got together and dated for a period in 2004, but it didn’t last - like many women on this list!
6 DATED: Minka Kelly
When Derek embarks on a relationship with a woman, people begin taking bets as to how long it will last. Two or three months are popular choices. But he dated Minka for far longer than his other conquests. Aside from his wife, he’s been with Minka the longest. They did break up for a while, but patched things up before going their separate ways again.
5 DIDN’T LAST LONG: Rachel Uchitel
Rachel Uchitel has become an infamous name in the celebrity world. She’s become something of a femme fatale after her association with Tiger Woods. But before Tiger fell for her charms, Derek Jeter dated her. Initially, they were just rumors, but then Rachel’s mom confirmed the two had indeed dated.
4 DATED: Jessica Biel
It’s fair to say that people were rooting for Derek Jeter and Jessica Biel when they got together. The duo really were a superstar couple. Many thought it’d be Jessica who’d make an honest man out of Derek. She tried but without success. It all worked out for the best though as the two are now married – to other people – and enjoying family life.
3 DIDN’T LAST LONG: Adriana Lima
Around 15 years ago, Adriana Lima was the new hot property in the modelling world. The Victoria’s Secret model was a permanent fixture in the minds of many guys at the time, including Derek’s in 2006. But his relations with the supermodel didn’t last long. Adriana went on to acquire a dating list almost as illustrious as the one Derek has!
2 DATED: Hannah Jeter
After many, many, many, failed relationships, Hannah Davis – now Jeter – was the woman who finally made an honest man out of Derek. His dating days, going from different woman to woman, month to month, are now over. The two got hitched in 2016 and have added a couple of kids to their family.
1 DIDN’T LAST LONG: Vida Guerra
Rumor has it that Derek had a little something going on with Cuban-American glamor model, Vida Guerra. At the time she was modelling for all the top companies, was gracing the covers of coveted spreads. If it did happen, it didn’t last long and was extremely casual.
Sources - ESPN, GQ, Digital Spy