There’s no doubt about it – Derek Jeter is one of the best players to ever swing a bat and lace up his shoes for the ball field. He basically became the face for the New York Yankees throughout his nearly 20 year career (all in New York), and served as the Yankees captain for over a decade in the latter half of his career. And, I mean, do we even need to go over his athletic accolades? The man won five World Series championships, five Gold Glove Awards, five Silver Slugger Awards, was a 14 time All-Star… I mean, this man was truly one of the best in the game. As soon as hints of his retirement began circulating, you know the Baseball Hall of Fame staff started working on Jeter’s plaque – it was an inevitability.
Now, while Jeter’s long career as an athlete means many of his achievements are tied to the game of baseball, he’s also known as having an extraordinary amount of game with the ladies. Jeter is a handsome guy and, thanks to his career as a professional athlete, has kept himself in fairly good shape over the years. However, absolutely nothing can account for the sheer amount of gorgeous women he dated apart from some insane amount of charm. After all, sure he attained more success and notoriety than many professional athletes do as he had a bit of an edge in skill, but at the end of the day, having a double digit amount of bombshell celebrities or supermodels in your little black book is a feat unto itself.
Every man on earth wants to know how he did it. In fact, though Jeter has more than enough money to live comfortably in retirement, should he get bored, we highly recommend he pen a book on how to pick up women. It would be an instant bestseller – just look at his track record.
We don’t know how you did it Derek, but you did. Here are 15 of the hottest women Derek Jeter has slept with.
15 Jessica Biel
Jessica Biel has had a long career in Hollywood, starting out as one of the Camden girls on wholesome family hit 7th Heaven. After her successful stint on the small screen, she began starring in films of a variety of genres, from romantic comedies to action movies, including Summer Catch, The Rules of Attraction, The Texas Chainsaw Massacre, Blade: Trinity and more. Throughout her career, one thing has remained consistent – she has frequently been featured on lists of the hottest women in Hollywood. Perhaps its on one of those lists that she first caught Jeter’s eye, as the two dated briefly during the 2006 MLB season. Now, Biel is happily married to pop star and actor Justin Timberlake, and the two had a son together this year.
14 Vanessa (Minnillo) Lachey
Nowadays, Vanessa Lachey is known as the wife of former 98 Degrees frontman Nick Lachey, and is happily settled down in married family life. However, back in the day, when she was still Vanessa Minnillo, she briefly dated Jeter. While Minnillo has carved out a successful niche for herself as a host and entertainment correspondent, back in 2003 when she was spotted with the baseball superstar, she was a VJ for former MTV hit Total Request Live. It was an on-again, off-again type of relationship, and the two called it quits after a brief period of time. After splitting with Jeter, she started to find a lot more success – perhaps it was a case of one celebrity’s fame overshadowing the other? With Lachey, as she got together with him after his boy band fame had cooled, the two have roughly the same category of star power.
13 Jordana Brewster
Jeter is known for being super low key about his romantic relationships, so he probably wasn’t too happy back in 2002 when The Daily News featured a shot of him and Jordana Brewster smooching and holding hands at his 28th birthday party. Hey, you can’t blame a guy – he was probably celebrating too hard and didn’t pay attention to the paparazzi. After that, the two were spotted together occasionally for a couple months and Brewster was apparently gushing to her girlfriends about the long term potential of the relationship. Does she know Derek? He’s not one to spend more than a few months with a girl, with one exception, so no one was surprised when they soon parted ways.
12 Joy Enriquez
Jessica Biel wasn’t the only 7th Heaven alumni that Jeter had his eye on – for a period in 2001, he dated 7th Heaven actress Joy Enriquez. Incidentally, Enriquez was also a back-up singer for Mariah Carey, another of Jeter’s former conquests – you could probably play a five degrees of separation game throughout the entertainment industry for Jeter’s former lovers! Jeter apparently poached Enriquez from A-Rod, who brought her to the 2001 All-Star game, as about two months after they were introduced she suddenly traded in Rodriguez for Jeter. There’s a lesson to be learned here, guys – no matter how famous you are, at the end of the day, what Jeter wants, Jeter gets.
11 Gabrielle Union
This former hook-up is a bit contentious, because both parties involved denied any romantic relations. However, let’s just look at the facts here. Apparently, not long after splitting from Hollywood hottie Jessica Biel, Jeter was spotted grinding at a nightclub in the Bahamas with actress Gabrielle Union. While Union’s rep denied anything but friendship between the two, as did Union, she also commented that “if I were dating Derek Jeter, trust me I’d announce it to the world.” Two people who are attracted to one another (who wouldn’t be attracted to mega-fox Gabrielle Union, after all?), at a sweaty nightclub in a tropical location? We’re betting there might have been a little more fuel to this fire than either of the two let on. Of course, now she’s happily married to basketball superstar Dwyane Wade, so it’s all water under the bridge.
10 Mariah Carey
Did Jeter hook up with Carey after her split from husband and father to her children Nick Cannon? No – this pairing actually happened way back in the day, in about 1997. Jeter was a promising new rookie getting his start with the Yankees and Carey already had some success under her belt thanks to the release of several critically acclaimed albums. It was a brief fling, perhaps born of Carey’s desire to date someone outside the entertainment industry, and fizzled out fairly quickly. There’s one notable thing that came out of this relationship, though – Carey was arguably the first celebrity that Jeter dated, so it may have been on her that he started practicing his foolproof seduction techniques.
9 Vida Guerra
Guys, you may not know Vida Guerra’s name, but you’ve probably perused all her curves at some point in your youth. She first came onto the scene with a sultry spread in FHM in 2002, and since then, has made her living as a glamour model posing for a variety of men’s magazines. Jeter reportedly snagged this Cuban cutie back in 2005, when she was still a young hottie constantly posing in a bikini. It didn’t last long (which of them do?) and it didn’t receive a lot of media attention (again, which of them do?), but according to ESPN, it definitely happened.
8 Rachel Uchitel
Okay, the designation of ‘hot’ is a little iffy in this example, but given all the scandal around Tiger Woods, it has to be said – he’s not the only athlete that Rachel Uchitel has slept with. The difference is, while Woods was a married man with a wife and children back home, Jeter was a single guy just enjoying his bachelor status with as many women as would let him. Before Uchitel started to unravel Tiger Woods’ life, she had a brief fling with Jeter. There’s a joke here about bats, clubs, and swings, but we won’t go there.
7 Bridget Hall
Derek Jeter seems to have developed two types over the years – gorgeous actresses and gorgeous models. Bridget Hall falls into the second category. Hall is best known for gracing the pages of the infamous Sports Illustrated Swimsuit issues in the early 2000s and Jeter apparently got a piece of that at the height of her swimsuit fame. Like many of Jeter’s relationships, this one is shrouded in a bit of mystery, but based on his track record absolutely no one has any trouble believing he could have scored this bikini-wearing bombshell.
6 Adriana Lima
That’s right – back in 2006, Jeter was spotted with Victoria’s Secret bombshell Adriana Lima. Collectively, men of the world gasp “that’s just not fair!” However, remember – this was back before Lima was married to her now ex-husband Marko Jaric, and the devout Catholic supermodel was adamant about saving herself for marriage, so chances are that Jeter didn’t get to go all the way with the Brazilian babe. However, even one or two bases with Lima is more than any guy could ever hope for. Having split with her husband, Lima has been rumored to have made some questionable romantic decisions (Bieber, anyone?) so who knows – maybe she’ll circle back to Jeter as a rebound.
5 Scarlett Johansson
Okay, we’re just going to say it one more time – it is absolutely criminal how many gorgeous women have agreed to accompany Derek Jeter places. One of them is sexy silver screen star Scarlett Johnasson. Nowadays, Johnasson is married to Romain Dauriac, someone entirely outside the world of Hollywood. However, back in 2004, she was spotted leaving a Christmas party with womanizer Derek Jeter. She shot down the rumors, but come on – how many of us have been to a holiday party where the liquor is flowing a little too freely and everyone gets a little, ahem, caught up in the holiday season.
4 Lara Dutta
It’s not enough to date someone who is making a living as a model in America – Jeter also wants to get his hands on someone whose beauty has been seen throughout the world. Case in point, Lara Dutta. Currently, the Indian-born Dutta is married to Indian tennis player Mahesh Bhupati, and the couple have a child together. However, shortly after she was crowned Miss Universe in 2000, Dutta spent a brief amount of time living in New York City. And what do you do when you’re a gorgeous woman in New York City? You date Derek Jeter, obviously.
3 Hannah Davis
This relationship isn’t one from Jeter’s best of archives – it’s a lot more current. Model Hannah Davis’ commercial modelling career has been going for the past few years, as she snagged jobs with brands like American Eagle Outfitters, Levi’s, and Victoria’s Secret. The bombshell definitely rocks a bikini and was accordingly given a spot in several of the Sports Illustrated Swimsuit Issues, including being the cover girl for the most recent edition. Jeter is about 16 years older than Davis, but hey – that charm counts for a lot. This beach babe has been Jeter’s on-agan, off-again pairing for the past little while, since about 2013.
2 Jessica Alba
Jessica Alba wasn’t content to merely be an actress. After marrying Cash Warren and having her first child, she decided to launch The Honest Company. Now, she’s as known for her business moves as her acting roles and she’s carved out quite a successful niche for herself in the industry. This mom of two has it all together, but back in 2004, she was another gorgeous actress lured in by the baseball star’s charms. Alba and Jeter briefly dated in the 2004 MLB season, but it wasn’t a long-lasting match.
1 Minka Kelly
While she made her biggest silver screen debut as the star of college horror flick The Roommate, you’ll probably know Minka Kelly best for her time as Lyla Garrity on beloved television series Friday Night Lights. And, it must be said, this is the woman who managed to keep Derek Jeter on the hook for far, far longer than any of his other women. The two dated from 2008 to 2011, broke up, and briefly reunited in 2012 before moving on for good. Towards the end of their relationship, there were even wedding rumors circulating as the media became impressed by the sheer amount of time Jeter spent with the Hollywood starlet compared to his typical relationship length. When her star power started skyrocketing, Jeter just couldn’t take the heat and the two split for good.