Derek Jeter had quite the successful career in baseball, to say the least. He spent his entire 20-year MLB playing career as a loyal shortstop for the New York Yankees. In his very first year on the team, 21-year-old Jeter helped bring the Yankees to victory in the 1996 World Series, and he was named Rookie of the Year. What followed were 19 more years as the Yankees’ star player. Although the 5-time World Series champion retired in 2014, he still holds the Yankees’ record for the most number of hits, games played, doubles, bases stolen, times on base, appearances on plate, and at bats. Over the length of his career, he won 5 Gold Glove Awards, 5 Silver Slugger Awards, 2 Hank Aaron Awards, and one Roberto Clemente Award. By the time he retired, he was ranked the 6th player in all MLB history in number of career hits and was number 1 among shortstops.
With a career like his, it’s no wonder why Jeter is still considered one of the highest-paid Major League Baseball players of all time. He played a total of 20 seasons, and his highest single-season salary was a whopping $22.6 million. His high earnings placed him on number 2, right behind teammate Alex Rodriguez, who made $33 million.
Besides being a famous professional baseball star, Jeter is also known for his life off the field. And when we say life, we mean specifically his dating life. It is not surprising that with success, money, fame and looks like his, he could easily land pretty much any woman he wanted. Well, that is exactly what Jeter did. Celebrity tabloids adored Jeter and all of the relationship gossip that came along with him. In the early 2000s, it seemed like he was popping up with a new date nearly every couple of months. And Jeter didn’t just appear with any random girl – he clearly had a type. And when we say type, we mean specifically beautiful fashion models and movie stars.
After years and years of seeing Jeter with numerous ladies, many of us were starting to wonder if the bachelor was ever going to settle down and commit to just one woman. In 2015, he shook the world with his news that he had finally found “the one!” Obviously, she is a stunningly young supermodel, but at least he finally put a ring on it!
We are truly happy for Derek, and to celebrate, let’s take a look at the (many) gorgeous ladies who came before Mrs. Derek Jeter.
Before Derek Jeter was a married man, he dated Minka Kelly. Minka is the only child of the former Aerosmith guitar player, Rick Dufay. Although she didn’t follow a career in music like her talented father, she is doing pretty darn well as an actress. The brunette beauty has appeared in several movies and television shows, but is probably most well-known for her role in NBC’s Friday Night Lights.
Derek Jeter and Minka Kelly (dated) 2008-2012
Minka and Derek were in a pretty serious relationship for four solid years. When they announced their breakup in 2012, fans everywhere were devastated. After making his way through several past relationships, the world thought for sure that the sweet and stunning Minka was finally the one he was going to commit to. Sadly, they just weren’t meant to be, and they both moved on with their lives.
Before the lovely Jessica Biel was married to Justin Timberlake, she actually was one of Derek Jeter’s (many) girlfriends. These days, she has quite the career, after getting her big break in the popular family drama show 7th Heaven when she was a teenager. She went on to achieve even more success, and is now considered one of the most gorgeous movie stars in Hollywood. Jessica is not only an actress, but also a proud mom to her and Justin’s adorable two-year-old boy.
Derek Jeter and Jessica Biel (dated) 2006-2007
The baseball pro and movie star surprised the media by publicly revealing their relationship in 2006. Although they did make a dashing pair, they just didn’t have enough in common and decided it was a good idea to part. Their brief romance lasted only a few months between 2006-2007, and ended before it ever really began. Luckily, it was long enough for paparazzi to capture some cute moments between the two lovebirds.
That’s right, Derek Jeter also managed to date the oh so beautiful Jordana Brewster. Jordana started acting in soap operas in the mid ’90s, and landed her breakthrough role as Mia Toretto in The Fast and Furious franchise in 2001. She has been married to Friday the 13th and Teenage Mutant Ninja Turtles film producer Andre Form, since 2011. The happily married couple are now parents to two children.
Derek Jeter and Jordana Brewster (dated) 2003
Back in 2003, Derek Jeter and Jordana Brewster had a pretty “fast and furious” romance. Although the entire relationship lasted for less than a year, the two were pretty public about their relationship status and posed happily side by side for the paparazzi. However, like most of Derek’s love interests, it didn’t lead to much and the two said goodbye and that was the end of that.
Okay, we are beginning to lose track on just how many supermodels Derek Jeter has been with… Bridget Hall started modeling when she was only 10 years old. The Texas native eventually moved to New York City with her mother in order to expand her modeling career, and she became one of the top 10 highest-paid models on Forbes’ list by the time she was 17. In the early 2000s, she appeared in multiple fashion magazines, but was most famous for her work in Sports Illustrated’s swimsuit issues.
Derek Jeter and Bridget Hall (rumored) 2000
Derek Jeter was rumored to be dating the famous swimsuit model during the early 2000s, at the peak of the model’s career and fame. The relationship between the two remained a mystery, and was never made official, like most of his relationships. However, with his track record we have no difficulty believing whatsoever that Derek could have scored with the bikini-wearing bombshell at one point or another.
Derek must have a thing for Jessicas… Jessica Alba is one of Hollywood’s most famous (and gorgeous) actresses. She started acting at the age of 13, when she appeared in her first role in the film Camp Nowhere. These days, she is beset known for her roles in movies like Fantastic Four and Sin City. She has been married to film producer Cash Warren since 2008, and the couple now have two children together, with one more on the way!
Derek Jeter and Jessica Alba (rumored) 2004
Derek Jeter and Jessica Alba were rumored to be seeing each other during the summer of 2004. Like many of his rumored relationships with overly attractive women, it was never made official, but it certainly does seem like a likely match. Sources said that Derek had a brief fling with Jessica while he was on break with his on-again-off-again girlfriend at the time, Vanessa Minnillo (more on her later..)
Another one of Derek’s love interests was none other than the breathtaking Scarlett Johansson. Scarlett has been gracing our screens with her presence since the mid ’90s. It seems like she is only becoming more and more successful and talented as the years go by. She has been in too many movies to count, but some of her most famous roles are from The Avengers, Her and Lost in Translation. We’re pretty sure there isn’t a movie with Scarlett that we wouldn’t see.
Derek Jeter and Scarlett Johansson (rumored) 2004
It is obvious that Derek certainly enjoyed himself while he was on a break with Vanessa Minnillo. And he just happened to pick the most beautiful women in Hollywood – that’s one way to get over a breakup! Scarlett Johansson was also one of the women with whom Derek reportedly had a relationship in 2004. Again, it was only a rumor, but one we are betting is true considering Derek’s history.
This leads us (finally) to the fabulous Vanessa Lachey (formerly Minnillo). The well-known actress and television personality got her start as a model and beauty queen, and was titled Miss Teen USA in 1998. Since then, she has appeared in several films and TV shows – most notably hosting MTV’s Total Request Live – and was a correspondent on Entertainment Tonight. In 2011, she married 98 Degrees singer and Jessica Simpson’s ex-husband, Nick Lachey, and they currently have three beautiful children.
Derek Jeter and Vannessa Lachey (dated) 2003-2006
Before Vanessa Minnillo became Vanessa Lachey, she had a bumpy on-again-off-again relationship with Derek Jeter for three whole years, from 2003 to 2006. Although the couple made for one adorable and super good-looking pair, it just wasn’t meant to be. The exact reasons of their breakup remain unclear, but Derek’s dating two movie stars while they were on a break may have had something to do with it. They allegedly stayed friends after split, and are said to still be friends today.
Joy Enriquez is a singer and actress who had a brief acting career that included a one-episode singing appearance on 7th Heaven. She has been singing since she was a young child, and participated in Star Search when she was eleven years old. She ended up landing a record deal and released her first single, Tell Me How You Feel in 2001. A few years later, in 2004, she married the record producer Rodney Jerkins, who had worked on her debut album. They now have four, very adorable, children and their own reality series called House of Joy.
Derek Jeter and Joy Enriquez (dated) 2001
Shortly after Joy’s first album was released, she was introduced to Derek Jeter by his teammate, Alex Rodriguez. The two hit it off right away, and started dating. Of course, like most of Derek’s flings, it was really just a “fling” and nothing more. Their “relationship” was over in only a few months… we are really starting to wonder how Derek ever decided to settle down.
The stunning beauty from India, Lara Dutta, was crowned Miss Universe in 2000, and was only the second woman from India to ever be given the title. After her win, she started landing several roles in Hindi films and is now one of Bollywood’s biggest stars. In 2011, she got married to the retired Indian professional tennis player Mahesh Bhupathi, and the couple now have one child together.
Derek Jeter and Lara Dutta (dated) 2000-2001
Should we be surprised that the woman who was named the most beautiful girl in the “universe” would get the attention of Derek Jeter? Yeah, we didn’t think so either. Shortly after Lara Dutta’s rise to fame from Miss Universe, she met Derek and they dated for a few months. She was actually one of his first ladies to make her debut as his courtside date.
Does Mariah Carey even need an introduction? The singing diva rose to fame in the early ’90s, shortly after she released her debut album, Mariah Carey, with Columbia Records. The natural talent and beauty became, and still is, one of the world’s most famous and successful musical artists. She made headlines in 2008 for marrying her second husband rapper/actor Nick Cannon (mega-music producer Tommy Mottola had been her first). Mariah and Nick divorced after an eight-year marriage, but share an adorable set of 6-year-old twins together.
Derek Jeter and Mariah Carey (dated) 1998
The songbird and baseball pro dated for about a year during 1998. The couple had an instant connection, and bonded over their shared mixed race heritage. Ultimately, the nonstop media attention and paparazzi caused too much pressure on the relationship, and they decided it was better to end things before it got too serious. Though they have both moved on, we wonder if they ever think back to the good old days when they were together.
Rachel Uchitel is a nightclub promoter, hostess and TV correspondent. She made headlines in 2010 when she was reported as one of pro golfer Tiger Woods’ alleged lovers while he was married to his wife and mother to his children, Elin Nordegren. After Tiger’s indiscretions were made public, Rachel’s fame continued to rise, as he wasn’t the only professional athlete Rachel has dated over her years in the public eye.
Derek Jeter and Rachel Uchitel (rumored) 2008
Before Rachel was about to unravel Tiger Woods’ life, she allegedly had a brief romance with Derek Jeter. It was a rumor, but one we tend to believe. In 2013, Rachel ended up marrying a (surprise surprise) athlete named Matt Hahn, who was a football star at Penn State and now works in finance. The couple, who became parents to a baby girl, got a divorce after a brief year and a half long marriage. Who will Rachel’s next athlete boyfriend be?
At this point, we are pretty sure that Derek Jeter has basically dated every supermodel from the early 2000s. Of course, Tyra is not just one of America’s most famous fashion models of all time, she is also a boss queen who created one of the most-watched reality TV shows ever, America’s Next Top Model. Tyra Banks dated her baby daddy, fashion photographer Erik Asla from 2013, until their recent breakup in October 2017.
Derek Jeter and Tyra Banks (rumored) 2001
It was just another rumor, but it makes sense that Derek (who by now we can all see that he has an obsession with models) would fall for one of America’s number one supermodels (we see you Miss Cindy), Tyra Banks herself. The two celebrities allegedly had a short-lived romance that ended after only a couple months. While we aren’t sure why or how it ended, one thing is clear… Tyra just didn’t make the cut to be Derek’s next top model. On to the next one.
And last on our list is, surprise surprise, yet another model! Vida Guerra is a Cuban-American glamour model who made her U.S. debut in For Him Magazine in 2002. Since then, she has been appearing in men’s magazines everywhere. In 2005, she had a bit of a scare, when her phone was hacked and some inappropriate and private pictures of her were released to the public. Luckily, she overcame the unfortunate incident and continued onward with her successful career.
Derek Jeter and Vida Guerra (dated) 1996
Way back when in 1996, a 22-year-old Vida Guerra dated the young New York Yankees rookie Derek Jeter. The two had a pretty steady relationship for some time, until Jeter’s career took off and they went their separate ways. When Vida found out about his marriage to Hannah Davis, she said that she was happy for him. “He said once he retired he wanted to get married, so he’s living his dream. Congratulations to him.”
Derek Jeter’s new wife, Hannah Jeter (formally Davis) is a supermodel who is probably best known for gracing the Sports Illustrated Swimsuit Issue on several occasions. She grew up in tropical St. Thomas in the U.S. Virgin Islands, and yes we are also super jealous. Hannah started modeling at the age of 16, when she was already landing jobs for Ralph Lauren. Since then, she has continued to model for brands like Victoria’s Secret, American Eagle Outfitters, Tommy Hilfiger, and Levi’s.
Derek Jeter and Hannah Jeter (married) 2016-
The model and former Yankees star confirmed their engagement in November 2015, and they were married the following year in an intimate ceremony at Meadowood Napa Valley Resort in St. Helena, California. Despite the 16-year age gap that stands between them, the pair make a sweet, and not to mention good-looking, couple. In August 2017, the newlyweds welcomed their first child together, a baby girl named Bella.
Another model on Derek’s list of past romances, is raven-haired bombshell Adriana Lima. The Brazilian model has been a Victoria’s Secret Angel since the late ’90s, and is currently the longest-running model in Victoria’s Secret history. She was even named the Most Valuable Victoria’s Secret Angel earlier in 2017. The supermodel is also a spokesmodel for Maybelline and has appeared in several Super Bowl commercials. She is currently number four on Forbes’ list of highest-paid models.
Derek Jeter and Adriana Lima (rumored) 2006
Derek Jeter and the famed model, Adriana Lima, reportedly dated for several months in 2006. Of course, their relationship status was never made official, but the two certainly seemed pretty close. A few years later Adriana went on to marry basketball player Marko Jarić and they now have two children together. Unfortunately, Lima and Jarić’s relationship didn’t work out, either, and the two got a divorce after a 7-year marriage in 2016.