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MLB's 20 Biggest Playboys Ever

Dan TylickiAnalyst IJanuary 14, 2017

MLB's 20 Biggest Playboys Ever

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    With Valentine's Day having come and gone, we can now get back to talking about baseball. More accurately, we can talk about the guys who took quantity over quality when it came to female suitors.

    These are the philanderers and playboys who could not only get top women, but tended to get a lot of them. Some are known as womanizers, and their reputations became just as much about that as their talent.

    Here are 20 of the all-time biggest playboys in baseball.

20. Louis Sockalexis

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    Louis Sockalexis was likely the first person with Native American blood to play in the majors, but he was also baseball's first playboy.

    During his first season with the Cleveland Spiders in 1897, Sockalexis injured his ankle after jumping from a brothel's window while drunk. His career didn't last much longer after that incident.

19. Ernie Lombardi

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    Of all the players on this list, Ernie Lombardi was by far the most unlikely sex symbol of any baseball player. After all, he had a big nose and was probably the slowest guy on the diamond.

    But he was a fan favorite in Cincinnati to begin with, and there were female Lombardi fanatics all across the nation. For whatever reason, women were drawn to him—although his activity paled in comparison to others on this list.

18. Chipper Jones

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    Chipper Jones has established himself in the past two decades as one of the all-time greatest third basemen. He has rebounded from his womanizing ways, but that was a big part of his earlier career.

    In 1998, he disclosed that he had an 18-month affair with a Hooters waitress, and had a son on top of that, leading to a divorce from his wife.

    His image wasn't hurt much from it, and he's still remembered fondly.

17. Jim Palmer

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    I was reluctant to put Jim Palmer on this list, since he was a reluctant sex symbol and a rather clean guy. Nonetheless, he gets on the list for one reason: He became a pinup, posing in his underwear for Jockey.

    As a result, he has a massive female fanbase. The number of women wanting him gets him on the list, though he's the exception as the only player on this list who we know never acted on that.

16. Paul Lo Duca

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    Paul Lo Duca was married to a Playboy model named Sonia for a time in the 2000s. This in and of itself doesn't get someone on this list, however—the size would likely be doubled if that were the case.

    What does get Lo Duca on this list is his divorce in 2006, brought on by his apparent affair with a 19-year-old. If you're married to a Playboy model, and that's not enough for you, you get on this list.

15. Josh Hamilton

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    Josh Hamilton did enough during his tumultuous minor league years and his couple of subsequent lapses to land on the list, though he tries to stay straight (despite his recent alcohol-related transgression).

    During his frenzies with alcohol and drugs, he certainly was a womanizer, going to strip clubs and the like. After rehab, he's stayed away from that, and perhaps could be talked off the list, but then most of the above would have to be removed as well.

14. Jose Canseco

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    Jose Canseco hasn't had any infidelity on record like others on the list, and if he had, he'd probably be the first to note it. His relationship history, however, is enough to get him on here.

    He divorced twice, and one wife, Jessica, posed for Playboy. He had another relationship last year that went south, and he went after the woman on Twitter, leading to a restraining order.

13. Van Lingle Mungo

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    Van Lingle Mungo only has one real playboy story to his name, which is a rather catchy name at that. The story, however, is a doozy.

    During a visit to Cuba in the 1940s, he was reportedly caught in bed with a married woman, and the husband found out. As a result, the Dodgers had to smuggle him out so that he would not be killed by the man.

12. Roger Clemens

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    A lot of Roger Clemens' demons came out in 2008 during court hearings, the biggest of which was his long-term affair with country music star Mindy McCready. This would be enough to get him on the list as is, but she was 15 at the time this all began.

    He reportedly had relations with several other women around this time, but his relationship with McCready launches him to No. 12.

11. Hal Chase

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    The question when it comes to Hal Chase was not whether or not he was a womanizer; the question was whether he was a womanizer or a gambler first.

    The latter perhaps cost him the Hall of Fame, as he was widely regarded as a great first baseman. Details about how much of a playboy he was are sketchy, however, given the era he played in.

10. Jason Giambi

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    Jason Giambi was one of the main targets of Jose Canseco in his books, and the question became whether he was more well-known as a ladies' man or a steroid user.

    That focus has moved to the latter these days, but during the earlier parts of his career, he certainly was a womanizer. In fact, Canseco noted that just as much as the steroid use.

9. Mickey Mantle

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    Back in the day, sportswriters were fairly good about keeping players' personal lives under wraps. As a result, we didn't find out how much of a womanizer Mickey Mantle was until much later in his career.

    His marriage to Merlyn was reportedly not out of love, and at his retirement ceremony, he had both his wife and mistress with him. The two never officially filed for divorce, though, so take that for what it's worth.

8. Joe DiMaggio

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    Joe DiMaggio's a tough one to rank, since his reputation as a womanizer makes it seem like he did more than he actually did. In a strange sense, it was almost the opposite of Mickey Mantle.

    Of course, marrying Marilyn Monroe didn't help those who felt he was a playboy.

    He was rumored to be in relationships with many other women after divorcing Monroe, including Marlene Dietrich, at least one Miss America winner and many others, though it's unclear who and how many women DiMaggio was really involved with.

7. Alex Rodriguez

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    Did Alex Rodriguez's womanizing ways top Yankee greats like Joe DiMaggio and Mickey Mantle? Perhaps it's because of the modern era and the public knowing more about celebrities, but I would certainly say so.

    He's dated several different celebrities recently, including Kate Hudson and Cameron Diaz, but what gets him on the list is twofold. First, during his marriage, he spent time with an exotic dancer. The level of intimacy is unknown, but one can presume.

    He also supposedly patronized prostitutes in New York and tried to get with one of the madams, for that matter. While it's another thing that technically hasn't been confirmed, there's an awful lot of circumstantial evidence on the matter.

6. Steve Garvey

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    Steve Garvey's playboy style actually hurt his reputation a lot more than others on the list, since he had an image as a clean guy and was in fact nicknamed "Mr. Clean" during his playing career.

    After marrying and divorcing 12 years later, he had a relationship with his secretary and two others and got one of the three pregnant. He then proposed to the third one, so what did he do after that?

    He began a fourth relationship and became talk show fodder after that.

5. Joe Pepitone

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    In the 1960s, a new Joe took over New York, one that was even more of a playboy than the one many likely thought would rank higher here. That player is Joe Pepitone.

    The power hitter was a rather vain person to begin with, which Jim Bouton wrote about in Ball Four. Beyond that, he divorced three times, married a Playboy bunny, got around with 150 or more women and even posed nude himself in the 1970s.

4. Wade Boggs

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    Wade Boggs didn't put up the kinds of relationship numbers that the top three people on this list did, but he's ranked so highly because of the way he went about it.

    In 1988, it was revealed that Boggs had an affair with Margo Adams, who accompanied him on road trips over the course of four years, and he was sued for eight figures as a result.

    Not only that, but she revealed the details of their relationship to Penthouse.

3. Pete Rose

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    Pete Rose is synonymous with being the all-time hits leader and is well-known for his gambling. His womanizing ways, as a result, actually take a backseat to that, even though he was as big a playboy as anyone else during his time.

    He was married and divorced twice, and he had an affair with a model while still married to the second. Beyond that, some biographers consider his womanizing up there with Ruth's, and there were rumors that he had a mistress in every National League city.

2. Bo Belinsky

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    Bo Belinsky on the field was far from a star, ending his pitching career with a 28-51 record. Off the field, he was a Hollywood-level stud.

    He had relationships with Ann-Margret, Tina Louisa, Connie Stevens, Mamie Van Doren and the list goes on from there during his playing career. He also married and later divorced Playmate of the Year Jo Collins.

1. Babe Ruth

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    If there's one person that could truly be called the biggest womanizer of any MLB player, it's the Sultan of Swat himself, Babe Ruth. There is account after account of him having women all the time and carousing throughout the night no matter where he was.

    He never let it affect his game, and the most surprising fact about his marriage from 1914 to 1926 was that it lasted that long, given his infidelity and playboy ways.

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