Baseball is America’s favorite pastime for many reasons. Even when the world is dark and people are losing their entire life savings during the Great Depression, or when a German dictator decided he was going to eradicate Europe of anyone that is different than he is, baseball flourished in this country. It has been there for the worst moments in American history and continues to survive, giving people a chance to escape the world and enjoy something that is magical and beautiful. From the venues to the fans, there is no atmosphere in any professional sport that rivals it.
Everything about baseball is fun. It is traditional. It is a sport that families pass down between generations. Sons and fathers attend games just to spend time with one another and share something special. Oh, and let’s not forget about the hot dogs and beer, right?
But that is why so many people want to become professional baseball players. They want to experience what it feels like to play in front of thousands of these fans, to be worshiped by the millions of baseball fans all over the country.
That is enough to convince most people to grab a baseball bat and start practicing but then they hear about how some of these men get paid millions, and we mean millions (Miami’s Giancarlo Stanton signed a $325 million contract thru 2027, and 14 other men have contracts with a value of $175 million or more).
There is one more benefit that most baseball players take advantage of, the women. The fame that comes along with being a professional baseball player, along with all of the millions, and the fact that you are a pro athlete, gives these men plenty of options when it comes to finding a mate. In fact, many of these men use it to their advantage and date celebrities, supermodels, and some of the most famous, and beautiful women, on the planet.
Here are the 15 most notorious daters in baseball.
15. Gary Sheffield: 3
List of Women: DeLeon Sheffield, Laurie Liss, Toni Fort
Long after his playing days have ended both on and off the field, Gary Sheffield found himself a woman that makes him a better person. His wife, DeLeon Shffield has been married to Gary since 1998 and they have shared a very long and happy life together. But before he found the most amazingly beautiful wife he could have ever landed, he was out there, playing the field.
At first, it was in Milwaukee, when he began his career with the Brewers before heading to San Diego. After just a year with the Padres, he found himself playing for the Florida Marlins, where he would remain until 1998. Maybe he found himself a good woman too soon. After his time in Miami, he played in Los Angeles, New York, and Detroit. The talent would have been there, he just locked himself down by then and was no longer a bachelor playing the field.
14. David Justice: 4
List of Women: Rebecca Villalobos, Halle Berry, Nicole Foster, Beverly Peele
Before we dive into the personal life of one of David Justice, we wanted to take a moment to really explain what made him such a great baseball player.
David was consistently hitting the ball and producing runs for whatever team he played for. In fact, for his career, he averaged 31 home runs, 102 runs batted in, 93 runs, and 28 doubles over a 162-game season while still hitting 0.279. Put those numbers into today’s game and he is a Top-5 baseball star each season.
Halle Berry, that is all you really need to say about David Justice’s dating history that really matters. No offence to all of the other ladies on his list, but it really does not get much better than Halle freakin’ Berry. But if you ask David Justice, he might disagree and tell you that Rebecca Villalobos is the hottest woman in his life. He has been married to her for a good 16 years now and they had two of his three children together.
13. Evan Longoria: 2
List of Women: Jaime Edmondson, Jamie Hanna
Evan Longoria gives us a chance to explain the meaning of quality over quantity.
Throughout this entire list, all of these men have multiple women, most of which you have heard of before, and the higher you go on the list, the more ladies you will see. But for Evan Longoria, he is a little different because he dated two women, publicly, the first was a Tampa Bay Bucs cheerleader, Jamie Hanna, who was easily one of the hottest in the NFL. The second was the last he would ever need to date, it was former Playboy playmate and super sexy supermodel, Jaime Edmondson.
Jaime Edmondson is so gorgeous that if you eliminated the NFL cheerleader from his list of girlfriends, you would still probably want him on the list as an honorable mention. Her red hair, long legs, and beautiful smile causes a perfect combination of beauty and sex appeal.
12. Josh Beckett: 4
List of Women: Holly Beckett, Leeann Tweeden, Danielle Peck, Whitney Hayes
For the majority of his career, Josh Beckett was a good enough pitcher to earn himself a starting spot for three of the biggest clubs in the league, the Florida Marlins, Boston Red Sox, and Los Angeles Dodgers. However, and this is something that most people probably do not realize, he never played the free agency market. He was drafted by Florida in the 1st round, second overall pick, at the 1999 MLB draft and then spent five seasons in Florida before being traded to Boston as part of the Marlins salary cap savings plan. He was later traded to the Dodgers making him one of the few two-time World Series champions to never use free agency to his financial advantage.
It also helped him in his personal life, where he cleaned up with the ladies including being publicaly linked to some of the more famous WAGs of our time. He dated Leeann Tweeden and could have stopped right there but also spent time with several other smoking hot ladies to create a quality roster that earns him a spot on this list.
11. Chipper Jones: 4
List of Women: Taylor Higgins, Jennifer Rutledge, Karin Fulford, Sharon Logonov
Chipper Jones was the All-American sports player that was a role model for millions of kids across the country. Everything about him was something anyone would want their children to look up to. He was an outstanding athlete that covered third base for the best team in baseball, the Atlanta Braves, for 19 seasons. He never left for more money or fame, he stayed with the organization that gave him his first big break in the Majors and was well-respected by fans from all over the country.
But then a story broke out about his cheating ways. He was married to Karin Fulford, his first wife, when he started having an 18-month long affair with Jennifer Rutledge, a waitress from a Hooters restaurant in Michigan, that produced an illegitimate child, a son. But somehow, he still came out looking like a role model because he knew how to handle it.
He had a press conference and apologized to the public, the fans, and the entire Atlanta Braves organization for his mistake. He came off so genuine that it is hard not to feel the pain he will forever feel from making a terrible mistake like cheating on your wife.
10. Jose Canseco: 5
List of Women: Leila Knight, Heidi Northcott, Jessica Sekely, Esther Haddad, Jessica Canseco
Not many people love Jose Canseco. Most people do not even like the man for what he did in 2005, they actually still hate him for it.
You see, he wrote a book, well, someone wrote a book with his name on it, and in it, he told about how he used performance enhancing drugs, or anabolic steroids, during his playing days. That alone would have been good for a tell-all book and would help sell a lot of copies. However, he then decided to take everyone down with him and started naming names of other players also using Performance Enhancing Drugs during their playing days. Since then, it has been hearings, trials, denials, and controversy surrounding an athlete’s performance which will continue forever thanks to him. If a guy does everything the right way and hits a ton of home runs, the first question isn’t how many records will he break, it is now whether or not did he use PEDs.
All of it started with Jose Canseco and since then, he has found himself become quite the celebrity, which he has used to his advantage if you take a look at that Google machine and look at all of these ladies.
9. Barry Bonds: 5
List of Women: Monika Jakisic, Jennifer Peace, Kimberly Bell, Liz Watson, Susann Margreth
Did he use steroids? Jose Canseco never mentioned Barry Bonds as one of the many athletes that were using anabolic steroids during the 90’s, but his name became synonymous with performance enhancing drugs because how can a human being hit 73 home runs at the age of 36 without using a PED? Or that was the perception about Bonds and people assumed without any evidence that he was using drugs, which he has not ever once admitted to or even been found guilty of doing so.
The only time he was found guilty was during an obstruction of justice trial surround the BALCO case and his testimony, which was later overturned by a vote of 10-to-1 in 2015. So he literally has nothing on file or on record that shows he used steroids or PED’s of any kind.
Meanwhile, in his personal life, Bonds found himself in trouble with child support and prenuptial agreements that ended up making him look like a bad guy when, in reality, he was not bad, he was paying his ex-wife, Susan Branco, $30,000 a month in child and spousal support.
8. Barry Zito: 4
List of Women: Amber Seyer, Ari Brugh, Susie Mora, Alyssa Milano
Barry Zito is best known for one thing, his 2002 season in which he was the Oakland Athletics Ace. He pitched incredible for that entire season and went a ridiculous 23-5, with a 2.75 earned run average (ERA), in 35 games, throwing 182 strikeouts and only 78 walks. He ended up winning the American League Cy Young that season, the only one of his career. He would not return to that level for the rest of his career between the Oakland A’s and San Francisco Giants.
But living on the West Coast helped him out with the choice of women and he did quite well for himself. He dated the infamous WAG, Alyssa Milano, before dating smokeshows like Amber Seyer, Ari Brugh, and Susie Mora. He took three women no one knew about and turned them into celebrities overnight because he helped expose their beauty to the world and for that, everyone should thank him. Right?
7. Brad Penny: 4
List of Women: Alyssa Milano, Eliza Dushku, Karina Smirnoff, Kaci Cook
When it comes to Major League Baseball players, Brad Penny is one of the largest based on a combination of his height and weight. He was by no means the tallest, but when you consider his weight as a factor in the calculation of his body mass index, you come up with a nasty number that helps to prove the point that looks mean nothing when you have fame, popularity, and money.
Brad Penny is 6’4″, 270 pounds. That creates a BMI, body mass index, of 32.9, which is among the heaviest in baseball, ever. Randy Johnson is a good example to showcase the difference in sizes. Randy was 6’11” but only weighed 225 pounds which created this thin body frame. However, in Brad Penny’s case, he was more robust than anything else.
It never stopped him from cleaning up with the ladies. He is a God to the bigger guys in this world and with good reason. He pulled the likes of Dancing with the Stars dancer Karina Smirnoff, Faith from Buffy the Vampire Slayer television series, Eliza Dushku, the infamous WAG, Alyssa Milano, and even an Oklahoma City Thunder dancer, Kaci Cook, who is now his wife.
6. Matt Kemp: 5
List of Women: Rihanna, Khloe Kardashian, Zena Foster, Felisha Terrell, Letoya Luckett
One of the saddest things to witness is a truly talented superstar like Matt Kemp battle injuries which have seemed to turn him into an afterthought even though he is only 32 years old. He has many years of baseball left in his body but having missed most of last season and a big chunk of 2012 and 2013, he has turned into a player looking for a job. That’s when the Atlanta Braves landed him and he is currently a part of something special that is happening in Atlanta, they are winning games and looking better than originally thought.
As far as his personal life is concerned, Matt Kemp was one of the Los Angeles Dodgers because weapons from 2006 until about 2014, making him the face of a legendary organization in one of the biggest celebrity towns in the world, Hollywood. He found himself dating Rihanna at one point, something not many of us saw coming, and also Khloe Kardashian, which is more like a rite of passage for athletes today anyways.
5. Hunter Pence: 5
List of Women: Alexis Pence, Savanna Sweetland, Lindsay Slott, Shannon James, Heidi Mueller
Although not considered one of the hottest baseball players in the Majors, Hunter Pence finds ways to do well for himself, which includes dating women that would stand near the top of this list if we were to break it down to the WAGs only.
Look at what he has done since entering the league with the Houston Astros in 2007. He dated a Houston Texans cheerleader, Lindsay Slott, a Soap Opera actress, Heidi Mueller, a Playboy playmate, Shannon James, and a sweet and innocent blonde named Savanna Sweetland. But he was not done there and went on to marry Alexis Cozombolidis, better known by nerds everywhere as Olivia Munn’s replacement on G4’s Attack of the Show.
4. Mike Piazza: 6
List of Women: Alicia Rickter, Darlene Bernaola, Lisa Barbuscia, Debbe Dunning, Anita Hart, Angela Nazario
In 2002, Mike Piazza hosted a press conference where he publicly came out and denied the rumors that he was a homosexual. There was a lot of rumors flying around that season that there was a gay player on the New York Mets and somehow it was linked to Mike Piazza, but he made sure the world knew it was false. At the time, it was a terrible decision and instead of coming out to claim he was not gay, he should have come out and asked the world what is the big deal instead. It would have caused a backlash that would have been minimal compared to the respect and admiration that he would have earned from defending the rumors, even if they were not true.
Years later, now that we see his amazing list of girlfriends, we understand why he did it. He was protecting his personal life. Based on the list of ladies above, what other reason would he have to come out and deny those rumors, started by the press, instead of ignoring something as meaningless to baseball as sexual orientation.
3. Matt Harvey: 7
List of Women: Adriana Lima, Anne Vyalitsyna, Ania Cywinska, Asha Leo, Ashley Haas, Devon Windsor, Shannon Rusbuldt
As you probably have learned by now, playing in New York, whether it be for the Mets or Yankees, means you will be able to pull some of the hottest ladies in your entire life, especially if you are talented like Matt Harvey, right-handed pitcher for the New York Mets.
Matt Harvey had two good seasons, 2013 and 2015, where he pitched in 55 games (367.2 innings), going 22-13 with a 2.50 ERA, 379 strikeouts, and only 68 walks. He was the key to the Mets pitching success and carried with him an incredible 9.3 strikeouts per 9 innings pitched. But he missed all of 2014 and has never been able to pitch a full season since, having recently been injured this year.
But injured or not, he is apparently popular enough among the ladies, especially the supermodels, that he has dated more supermodels than anyone else on this list, outside of the top two. There is just something about those Russian supermodels that he cannot help but chase after.
2. Alex Rodriguez: 16
List of Women: Jennifer Lopez, Anne Wokjcicki, Julianne Hough, Torrie Wilson, Erin Simmonds, Kyna Treacy, Ella Magers, Demi Moore, Cameron Diaz, Kate Hudson, Elaine Spottswood, Bethenny Frankel, Meliss Britos, Madonna, Joslyn Noel Morse, Cynthia Scurtis
Whatever happened to Alex Rodriguez?
By the time he was 27 years old, Alex Rodriguez, better known as A-Rod, had 345 home runs, 1,009 runs, 990 runs batted in, 285 doubles, 177 stolen bases, and was a .308 batting average. He was easily heading towards a Hall of Fame career with just about every record you can think of, being broken. But then he went to the New York Yankees and his career changed. He slowly started to decline after his amazing 2007 season and he found himself with only one World Series ring, something he probably thought he would have had almost five during his time in New York. But his on the field play was nothing compared to his off the field play.
If not for his teammate, Derek Jeter, Alex Rodriguez would own the top spot on our list. However, when you break down the two lists of women between A-Rod and D.J., you get a much sexier one from the man they call Derek Jeter.
1. Derek Jeter: 16
List of Women: Hannah Davis, Bridget Hall, Vida Guerra, Scarlett Johansson, Minka Kelly, Adriana Lima, Jessica Biel, Jessica Alba, Vanessa Minnillo, Jordana Brewster, Joy Enriquez, Lara Dutta, Mariah Carey, Tyra Banks, Rachel Uchitel, Gabrielle Union
Who is Derek Jeter and how does one man score so many beautiful women?
For starters, he is probably the most respected New York Yankee in franchise history, playing his entire career for the Yankees while bringing the city of New York (Well, the Yankee side of New York at least) five World Series titles between 1996 and 2009. On top of the World Series wins, he is also a 19-year starter at shortstop who owns the team career records in hits (3,465), singles (2,595), doubles (544), stolen bases (358), strikeouts (1,840), at bats (11,195), and games played (2,747). That in itself makes him one of the greatest, if not arguably the second greatest Yankee of all time, behind Babe Ruth of course.
So besides dominating the Majors each season, he is not a bad looking dude either and he has a reputation for being such a good guy that the women were just drawn to him. It never hurt that he played in New York and had an entire city behind him, telling him how great he is all the time.
From Scarlett Johannson to Jessica Biel, Derek Jeter claimed the hearts of more Maxim Hot 100 hotties than just about any other athlete, ever. Even Wilt Chamberlain never claimed to have as many female celebrities as D.J. did during his playing days.
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