They went from the best of friends, to complete strangers. For a while, Derek Jeter and Alex Rodriguez were considered one of the best duos in baseball. A lot of merchandise was sold of the two of them linked together as a pair, and for a while, it seemed that they were a pair of really good friends. Things turned for the worse, and many claims say the two aren’t on good terms, so much that Derek Jeter didn’t even invite A-Rod to his wedding. But, before there was this drama and before Jeter got married to Hannah Davis, there were two men who were absolute sluggers when in came to women.
The Captain and A-Rod both have a long list of women they dated. And for a lot of the women on the list, it’s a pretty impressive bunch. Sometimes athletes aim for quantity, but in Jeter and A-Rod's case, they swung for the fences and hit one out of the park. It’s a tough battle to decide who had the more decorated dating resume, but we'll try to look at both men's lineups and you can decide for yourself. Who would ever think, Derek Jeter and Alex Rodriguez as two of the biggest “players” off the field?
20 Derek Jeter - Bridget Hall
Back in the good ole’ days, Derek Jeter was dating former Sports Illustrated model, Bridget Hall. When she was only 17 years old, Hall was listed in Forbes as a top 10 moneymaking supermodel. Her career has been over for a while, but she has been on covers for Vogue, ELLE and Allure. She’s modeled for these magazines in some of the biggest cities including New York City and Paris. Along with modeling for magazines, she also did some work for Pepsi and Guess Jeans. When she caught the eye of the superstar shortstop, she was currently modeling for Sports Illustrated.
By 2005, Hall’s career suddenly started diminishing. Bridget's career disappeared, as she became less and less notable as time went on. Something Derek would probably like, huh?
19 Alex Rodriguez - Alicia Marie
Ok. But the sweatpants I have on are everything — DO👏🏽YOU👏🏽HEAR👏🏽ME?!? 😆❤️💪🏽 I’m feeling super low key in Nov and kinda loving it... Thanksgiving: I AM cooking lmao - but @warcraft and sleeping the rest of the day so... Peep flip my comfiest fitness look by @ryderwear - camo hooded vest and these sweats tho 😱😳😍 ➡️ Ryderwear.com/Alicia It’s BLACK FRIDAY week and the sales on the site are insane...nows your chance to get all the stuff you’ve been looking at all year with slashed prices —— DONT MISS ITTTTT #ryderwear 👏🏽❤️🙌🏽☺️ #alicia #fitspo #fitfam #instadaily #aliciamarie #ryderwear #blackfriday #ootd #comfy #instafit #motivation #abs #ad #lean #muscle #girlsthatlift @fentybeauty #250/340 #makeup
Neither A-Rod or Alicia Marie has admitted to it, but it seems pretty certain that the two dated for a while. Alicia Marie is a fitness model, who appears in a lot of magazines. She’s incredibly fit, way beyond what many models actually are. The weird thing about this situation, is at the time, Alicia was dating former relief pitcher John Rocker, whom most fans remember for his racist and homophobic remarks in a Sports Illustrated interview. Sometimes though, things happen between people in relationships, especially those with fame. And if Alicia had a chance to upgrade for a disgraced former star to a legend, there’s many doubts that she wouldn’t take that chance. We sure wouldn't put this alleged hookup past A-Rod.
18 Derek Jeter - Rachel Uchitel
Whenever Jeter dates someone, it can always be a mystery as he tries to keep his love life as silent as possible. But even Rachel Uchitel’s mom confessed that the two was dating, so why did they have to try and avoid talking about it? Uchitel has plenty of fame from many different things. She started her career in television, working as the producer for the Bloomberg News. She then decided to change things up, as she got into the nightlife business in Las Vegas. There, she became a VIP host at Tao Nightclub. She was also overseeing popular nightclubs in New York City, such as Marquee and Stanton Social.
It seems that Uchitel has had some issues with holding a relationship, as she has had some problems keeping relationships going, and has been divorced twice. A big part of her fame came when she was known to be one of Tiger Wood’s mistresses.
17 Alex Rodriguez - Demi Moore
Alex Rodriguez was really into those older women, as he dated someone 13 years older than him. That’s more common when the male is older than the woman in sports, but Demi Moore was gorgeous back in her prime. Moore has been all over television, as one of the most popular shows she has been on is General Hospital. She was paid $12.5 million in 1996 to star in the movie Striptease, which paid her at the time, the highest paid actress in film history. The film turned out to be a huge disappointment, which led to the decline of her career. The only positive that could have been taken out of that year was the fact that Moore played the voice of Esmeralda in Disney’s The Hunchback Of Notre Dame.
16 Derek Jeter - Vida Guerra
Now we’re really talking. We know Derek Jeter has game on the field, but he really does have game off the field too. Guerra has been in plenty of music videos and appeared in commercials, National Lampoon’s Dorm Daze 2, and even a Scarface video game. Guerra is most known for her modeling pictures, as her body is breathtaking. In 2005, FHM voted Vida Guerra 26th on their Top 100 Sexiest Females list. Twice, she has been the winner of the magazine’s “Best Butt Award.”
These may be some unusual recognitions for some, but for Derek, he knew he scored right. Jeter wouldn’t have been in a bad place either had he have stayed with Guerra, as she even spoke positively about Jeter’s new girlfriend/now-wife Hannah.
15 Alex Rodriguez - Elaine Spottswood
Maybe Alex can’t always compare to Derek. Elaine Spottswood is a much more lowkey woman, than most of the other women he has ever dated. Unlike many of the other women on this list, Spottswood had no fame, despite the fact that she was dating one of the most well-known athletes in sports. She comes from Key West, Florida, and worked as a commercial tenant representative for the real estate firm, Howard Ecker and Co. Spottswood stayed away from the spotlight while they were together, and they weren’t really together for long, so it was easy to stay in hiding. A-Rod hasn't been in many relationships for a long period, so it wasn't much of a surprise that this one didn't last long.
14 Derek Jeter - Gabrielle Union
Before there was a Dwyane Wade in the picture for Gabrielle Union, there was a Derek Jeter. Union is known mostly for her appearance in many romantic comedy films, such as Think Like A Man, Bad Boys II and Daddy’s Little Girls. Union even was a part of popular films like Bring It On and She’s All That. Gabrielle claimed that the two never dated, but they were heavily rumored to have hooked up.
Hopefully Dwyane Wade and Derek Jeter aren't running into each other at parties, especially if Wade wants to make his way back to the Miami area to rejoin the Heat, and live in the same city as Jeter, who's now a part owner of the Marlins. Even with Union and Jeter both happily married to others, it would be pretty ironic to see them both living in the same city with their history.
13 Alex Rodriguez - Melissa Britos
These men are pulling women from around the world, it’s insane! Alex Rodriguez once hooked up with international model, Melissa Britos. One of the most gifted models out there, it was rumored that Rodriguez was cheating on Madonna with Britos. Wonder if she knows that the two was together… But if so, she may not have cared because eventually the two-started dating. Rodriguez and Britos apparently met at the Fontainebleau Hotel in Miami Beach, Florida. It wouldn’t be surprising considering how popular of a hotel that is to the city of Miami.
Some reports even claim that Rodriguez was obsessed with Britos, which is hard to believe considering the number of women he’s been with. He clearly wasn’t obsessed enough to put a ring on her.
12 Derek Jeter - Scarlett Johansson
This is another rumor that another woman denied; maybe this is just a case of wanting to keep things private? Derek was always caught around other women, but would try and constantly play it off like nothing was going on. But to be with a woman like Scarlett Johansson, that’s a woman to be proud to be with. She was among the highest paid actresses between 2014 and 2016. Some may look at her as the Black Widow, from the Marvel Cinematic Universe. While the two were supposedly together, Johansson was still quite young, yet already a few years into adulthood. She even started a singing career, as she has been on multiple soundtracks, including the soundtrack to The Jungle Book.
Johanssen certainly makes a strong case for Jeter's lineup.
11 Alex Rodriguez - Cameron Diaz
Sometimes relationships don’t tend to end the way you want them to, but apparently a close source to both Alex Rodriguez and Cameron Diaz, said that after the two broke up, they remained fairly close. Diaz is one of the most popular actresses in the past generation. Known for some of her many steamy moments in movie history, as well as her humor in movies, it was always great watching her on film. Some of her best performances came in Charlie’s Angels, Bad Teacher, What Happens In Vegas, and she was even the voice of Princess Fiona in the Shrek series.
So each man has dipped their toes into Hollywood, with both dating big-time movie stars. It's like these two can't stop competing.
10 Derek Jeter - Jessica Alba
The Captain never disappoints Jeter was hooking up with some of the most stunning actresses at the time. In 2004, Jeterb was linked to actress Jessica Alba. Jeter’s relationship with Alba came just after she and Michael Weatherly split up. Alba was pretty young at the time, and even admitted that when she accepted Weatherly’s proposal, she was still a virgin.
Alba is known as one of the best-looking actresses of all time. Alba has starred in many movies, but some of the most popular include Fantastic Four and Knocked Up. She’s also been in plenty of TV shows, including Entourage. Besides Alba’s fame on the camera, she is also known for her charity work, and involvement with politics. Jeter definitely hit one out of the park here.
9 Alex Rodriguez - Kate Hudson
Cute, innocent looking women aren't really the type of women you would expect Alex Rodriguez to go after. But, sometimes these professionals surprise you. Kate Hudson is another popular movie star, who has been in Fool’s Gold and Deepwater Horizon. Hudson also co-founded a fitness brand and membership program named Fabletics. It was around 2008 when Hudson and Rodriguez were seen together as a couple. Poor Hudson, as she had to deal with a guy who couldn’t get over his ex-girlfriend. A-Rod would call her constantly, even when Hudson gave A-Rod three chances to make things right. Rodriguez could never do that, so Hudson had little choice but to break up with him. Hudson was also nervous that her parents didn’t like him, so it was best to just cut their ties.
8 Derek Jeter - Adriana Lima
Adriana Lima could probably compete with Derek Jeter and Alex Rodriguez for people she’s been with too. Lima is one of the most famous Victoria Secret Angels, so it’s no surprise she caught the eyes of Jeter. Adriana is the longest-running model currently, as she started her career in 1999. She’s still one of the best-looking models around at 36 years old. Age doesn’t affect her one bit. Lima also won the Most Valuable Victoria Secret model in 2017.
The two didn’t date for long, probably because Lima wanted to get serious, and that wasn’t necessarily in the plans for the star shortstop at the time. Jeter was younger when the two were together, and Jeter didn't have any plans of getting married until after he retired from baseball.
7 Alex Rodriguez - Torrie Wilson
Alex Rodriguez is big and all, but Torrie Wilson can still probably take him down to the floor. Wilson is unique from the rest of the women on this list, as she’s a former WWE Diva. It’s actually pretty surprising that you wouldn’t see more of them on this list, considering that the WWE Divas when these gentlemen played baseball were some of the finest in WWE history. Maybe they were afraid of getting embarrassed by a tough woman?
Besides wrestling, she also posed for Playboy and FHM. She was seen to be a sex symbol to some. After her career finished, she actually got into fitness, and that is when she was dating Alex Rodriguez. The two dated for three years, but eventually broke up because A-Rod could not commit to something long-term. Sources claimed that Rodriguez would continuously flirt with other women while the two dated, which made it harder for Torrie to stay in the relationship.
6 Derek Jeter - Minka Kelly
The most natural beauty on the list is one that only The Captain would be able to land. Ironically, Minka Kelly starred in Charlie’s Angels, alongside one of A-Rod’s ladies, Cameron Diaz. She’s also known for playing a part in Friday Night Lights and Just Go With it. As such, she’s been both around movies and TV shows.
Minka Kelly has one of the most beautiful eyes and smiles, and it all seems so natural. If Derek was going to settle down with any of these women, Kelly looked like the one for fans, but clearly things didn’t work out too well with them. Jeter liked to keep his relationships as secretive as possible, and once Minka Kelly started gaining fame, that was the end of it.
5 Alex Rodriguez - Julianne Hough
Talent doesn’t always come with acting you know. In fact, this beauty can really move on the dance floor. Julianne Hough is known for her fame from ABC’s Dancing With The Stars, as she’s a two time champion on the show. In 2014, Hough actually joined the show to become a permanent judge. Hough does have experience with music and acting, but her main talent comes from her dancing skills.
There have been some rumors that A-Rod hooked up with Julianne Hough, even though Hough has said that she’s actually turned down multiple dates with Alex. You have to give credit to Alex Rodriguez for asking though, unless he was just trying to make his ex-girlfriend jealous of him to eventually get the two back together.
4 Derek Jeter - Mariah Carey
What the world wanted to see was for Derek Jeter and Mariah Carey to get married. It would have meant two of New York’s biggest stars being together forever, and would have be an incredible story. Even at 47 years old, Mariah can put many women to shame. Carey just has a smile that sends so many messages, and she just doesn't seem to age
Carey was still technically married to music executive Tommy Mottola when Derek ended up in the picture. The two started dating in 1996, before Derek was even known as the man in New York. In 1998, the relationship came to an end like all of Derek’s relationships, due to the over involvement of the media. Fortunately, Jeter kept bouncing back.
3 Alex Rodriguez - Jennifer Lopez
J-Lo needs no introduction. She was the first ever Latin actress to make over $1 million in a film. That eventually led her to the privilege of calling herself, the highest-paid Latin actress in Hollywood. Lopez has starred in many movies, but her most famous include Jersey Girl and The Wedding Planner. She’s also starred in TV shows, and has toured for many years. Lopez has been married three times before, with her longest marriage lasting 10 years with Marc Anthony. Much like Mariah Carey, J-Lo continues to look amazing late into her 40s.
There's somewhat of an age gap between Rodriguez and Lopez, but if you're dating J-Lo, do you really care? Lopez and A-Rod have been together for about a year now and by all accounts seem very happy together.
2 Derek Jeter - Hannah Davis
At last, Derek Jeter found the woman he will spend the rest of his life with, we hope. Reports of the two dating started lingering around when Derek was in his last couple of years in the MLB. Hannah actually wrote an incredible piece of The Players' Tribune, talking about the Derek she knows, and how she didn’t really know the Derek that New York knew.
In 2015, Derek finally popped the question, and the list ends right there for him. Derek got everything he wanted, as he is married to a supermodel who isn’t really all that famous, so they don’t have to worry about the media knocking on their doors all the time. The Jeters got married in July 2016, at a resort in California. Even better for the couple, they had their first-born child on August 27th, 2017, named Bella Raine Jeter.
1 Alex Rodriguez - Madonna
That girlfriend that Alex Rodriguez couldn’t stop obsessing over, yes, that was Madonna. There have been reports that while A-Rod was dating other women, he would have ongoing commitment issue due to his everlasting love for Madonna, and his non-stop messaging her. Madonna in her prime was one of the beautiful, yet incredible singers of her time. For some reason, Alex just couldn’t ever get his mind off of her, no matter how much time had passed since the two were together. However, it finally seems that Madonna is out of Rodriguez’s mind.
We don't know if A-Rod is quite done testing the market just yet, but if he was going to marry anyone, now would be a good time, with his MLB career being over.