Who out of you can say you won five World Series? Who can say that they won five Silver Slugger Awards? Who can say that they were a 14-time All-Star? If at least one of you can say yes to all of those, there is only one thing we would like to say: Mr. Jeter, it is an honor to have you here, sir. But on the very likely chance that no one answered yes to those questions, fear not. You don’t need to be an MLB All-Star in order to appreciate a fine “not so PG” picture. Sure, professional baseball players are connoisseurs of this art. Just go out with a current or former Yankee in New York, and you will get a taste of what a night out with these guys is like.
But back to the topic, let’s make it clear to everyone that even within the realm of professional baseball players, few if any other guys ever showed to the world that they have the kind of game Derek Jeter has. No, we are not talking about his ridiculously productive and glorious career on baseball fields across America. No, we are talking about a more important kind of game. His game with the ladies.
Jeter was a monster off the field. This guy could pull off hook ups with women Tiger Woods might not have had a chance with. And that is some strong company to be compared to on this subject. Nevertheless, Jeter is the man, and we have separated 15 “not so PG” pictures of women this New York legend has hooked up with.
15 Lara Dutta
We will start our list a little far from North America. More specifically speaking, we will head down to Asia and land in the second most populous country in the world, A.K.A. India. One of the most spiritual and fascinating countries on the globe, India is also the motherland to the beautiful Lara Dutta Bhupathi.
Dutta is an Indian actress and model who has won several beauty pageants around the world. Two of her big-time wins came in the 1997 Miss Intercontinental competition and the 2000 Miss Universe. She supposedly met Jeter after he had just broken off a relationship with an actress whose name we will mention later. It turns out their relationship must’ve been a good one as Jeter and Lara ended up dating for about one year.
14 Jordana Brewster
The second entry on our list is a beautiful woman who also must know her way around fast cars. That is because Jordana Brewster is not just a Derek Jeter conquest. She is also one of the stars of one of the most successful franchises in the history of Hollywood. While you might not remember Brewster as a former Derek Jeter girlfriend, you might remember her as the lovable Mia Torretto from the Fast and The Furious.
But while in the movies she maintained a loving relationship with the cop turned criminal Brian O’Conner, her taste in men in the real world seems more exquisite, as instead of a felon she ended up dating a baseball superstar for quite a while. Acting-wise, Brewster has been a big success playing a main role in the new Lethal Weapon tv series.
13 Vanessa Minnillo
These days she likes to be called Vanessa Lachey, but for all intents and purposes, we will refer to Vanessa Minnillo by her single lady name, since that was how she was called when she became involved with Derek Jeter. Born in Angeles City in the Philippines, this multi-talented woman became quite famous because of her beauty.
Participating in beauty pageants, she won titles like the Miss South Carolina Teen USA in 1998 as well as the Miss Teen USA in 1998. In 2003 she met and started dating a young man by the name of Derek Jeter. Their relationship lasted for nearly two years as it ended in 2005.
After her stint as Jeter’s girlfriend, Minnillo managed to find a man with whom she could spend her life with as she began dating singer Nick Lachey in 2006 and eventually married the man and adopted his last name in 2011.
12 Joy Enriquez
Summer loves as sometimes the most memorable of short term relationships. We can almost certainly guarantee that even a guy like Derek Jeter would not forget a summer love like this one. It was the summer of 2001 when the then young baseball star began dating the talented actress Joy Enriquez. A beauty with a lot of talent, this California girl also found success in the world of music.
At only 11 years old she had already made her first break into the music industry as she hit it big in Star Search and eventually landed a solo record deal with LaFace Records. Her relationship with Jeter did not last long, but Enriquez did manage to find love as she married producer Rodney Jerkins and the couple has four children.
11 Tyra Banks
Few women in the world of fashion and entertainment embody the trait of success as the American model and personality Tyra Banks.
People who are familiar with her today would probably find it hard to believe that when she was starting out in her teens, Banks was rejected by four different modeling agencies. It took one helpful agent and a chance to model in Europe for Banks to find her footing in the vicious world of fashion. Either way, one chance was all that Banks needed, as she took her one shot and knocked a home run out of the park (pun intended).
She became a world sensation and got all of the perks that come with the title. One of those perks was that she got to meet other famous people, and of course one of them was a guy named Derek Jeter.
10 Jessica Alba
Much like our last entry, Jessica Alba is a global celebrity. It doesn't matter which continent or country you decide to visit. The odds are enormous that everyone you meet will have at least seen the face of this California gal on a movie poster somewhere. Fantastic Four, Dark Angel, Sin City, and The Love Guru are just a few of the big and small screen hits that Alba has on her extensive resume.
In the relationship spectrum, Alba dated other celebrities of the caliber of Michael Weatherly, who co-starred with her in Dark Angel. She eventually married Cash Warren, the son of famous actor Michael Warren. They have two daughters. Before that, she supposedly dated Jeter while he was on a break from Vanessa Minnillo.
9 Bridget Hall
Some models start out in their careers at a very young age. Those are the babies you see in commercials and children who happily eat cereal bowls in advertisements. Bridget Hall was one of these kids who started their modeling careers very early. By the time she was 10 years old, this Arkansas native was already Modelling in Dallas.
When you put together how beautiful she became as she grew older, along with all of the experience she must have acquired after being part of this world for so long, it is not hard to understand why Bridget Hall became such a famous model.
Her dip into the sporting world came as she worked with Sports Illustrated, and from there, it is no surprise that she would meet a famous athlete like Jeter and go on to have a relationship with him, even if it was a brief one.
8 Rachel Uchitel
We mentioned Tiger Woods before, and there is a good reason for that. Sure, Tiger became notorious for his escapades and cheating, but he and Jeter do have something in common. These two have an almost unnatural ability to woo beautiful women. It was only a question of time until we found one common denominator between the two, or in other words, one woman that both of these guys hooked up with. And the spot where their love lives cross is the nightclub manager and hostess Rachel Uchitel.
Uchitel made several headlines after she was allegedly pointed as one of the many mistresses with whom Tiger had affairs while he was married. The weird thing here is that Uchitel said that one of the odd things Tiger told her was that he dreamt they were married, and one day he came home and found her in bed with Jeter and David Boreanaz. Weird, Tiger, too weird.
7 Vida Guerra
When Derek Jeter decided it was time to settle down and get married, one of the first women TMZ went after for comments was his former girlfriend, Vida Guerra. Unlike many people would imagine, this ex-girlfriend was more than happy to find out that her former paramour had finally found happiness and someone he would want to grow old next to.
“He said once he retired he wanted to get married .... so he's living his dream. Congratulations to him," she said.
Out of the many reported ex-girlfriends of the baseball star, Vida was one of the first few who found romance with the legendary Yankees number 2. That also means she might also be one of the few who actually had time to get over Jeter and find a way to wish him happiness on his next chapter. It probably also helps that she knows she is hotter than a lot of his other conquests.
6 Mariah Carey
Mariah Carey might just be the most famous woman Jeter has ever hooked up with. While she has dabbled in acting here and there, Carey is known around the world because of her finely tuned vocal chords.
Since we have baseball fans in the audience, let’s talk stats for a moment. Sorry, but we can’t really calculate Carey’s batting average or ERA, but the one thing we can do is show you the numbers when it comes to her music awards. In total, Carey has tallied more than 440 nominations and won over 270 awards in the music industry. Among those are 32 Billboard Music Awards, 20 World Music Awards, and 5 Grammys.
Jeter-wise, Carey dated the Yankee legend in the late 1990s. A fun fact here is that the Grammy winner is either four or five years older than the former Yankee captain.
5 Minka Kelly
If Vida Guerra was one of Jeter’s exes who seemed mostly okay with him finally tying the knot with someone, Minka Kelly was actually the first woman with whom it really seemed like Jeter would marry her. Their relationship was rocky at times, but for all intents and purposes, they were together for more than three years. Of course, it came as a shock to everyone that in 2012 the two announced that they were splitting up for good.
Professionally, Kelly is one hell of a successful actress with parts in ridiculously popular series like Friday Night Lights, Parenthood, and Charlie’s Angels. In terms of movies, her most recognizable roles were in pictures like The Butler and The Roommate. For her acting on that second flick, Kelly was nominated for an MTV Movie Award for Best Scared-As-S**t Performance.
4 Scarlett Johansson
Does this lady really need an introduction? Seriously, if there is one rumored Derek Jeter conquest that will have men sulking more than any other is this one. It was never confirmed that these two actually hooked up or had any kind of romantic relationship. But when a woman like Scarlett Johansson is tied to it, even a mere rumor is worth being added to a list like this one.
Apparently, the two of them hooked up while Jeter was on one of his many breaks with Vanessa Minnillo. And here we have to add that this has to be the epitome of a hookup during a break. It would take a legendary man such as Derek Jeter to pull off such a boss move.
3 Hannah Davis
Finally, we have arrived at the lady who managed to hold on to Derek Jeter. The improbable had finally happened when the two announced their engagement in 2015. Furthermore, the hearts of the many Jeter hopefuls finally received a final stab in July of 2016 when Jeter and Davis got married. Earlier this year, in February, the couple announced that they were expecting their first daughter.
Before getting married, Hannah Davis, or better yet, Hannah Jeter, was a successful American model. Like a few other names on our list, Davis is best known for her work when she appeared on issues of Sports Illustrated, which included a cover appearance in the 2015 edition of the Sports Illustrated Swimsuit Issue. Other fun facts about Hannah are that she played for the Virgin Islands’ national volleyball team and won a championship in the Caribbean Tennis Circuit.
2 Adriana Lima
Out of all the professions where beautiful women gather, it is tough to find one that can even get close to matching Victoria’s Secret Angel. These women do indeed look like angels. And even among those select few, you could still count on your fingers the ladies who could hold a candle to Adriana Lima in terms of beauty.
This Brazilian wonder has been a Victoria’s Secret Angel since 1999. She is the model who has held down the title for the longest time, and we will be damned if she doesn’t deserve it. Her net worth is estimated around $75 million. It doesn’t come close to Jeter’s reported $185 million, but it is impressive nonetheless.
The relationship between the Brazilian model and the baseball star did not last long, but it sure made headlines all around the globe while it was going on.
1 Jessica Biel
We have listed tons of beautiful women on this list. The easy conclusion is that there is something about Derek Jeter that has always drawn beautiful women to him. Models, singers, actresses, promoters and many others have found their way into short and long term relationships with the former Yankee captain.
Still, what was perhaps the most talked about relationship Jeter ever took part in was his relationship with Jessica Biel. The two were together for almost a year, and it seemed like every time these two left their homes there was a paparazzi camera pointed at them.
More than dating Jeter, Biel was famous for her superb acting. She rose to fame by starring in movies like The Texas Chainsaw Massacre, Rules of Attraction, and The Illusionist.
Today she is married to Justin Timberlake, and they have one son.