Top 15 Biggest Womanizers in Sports

Top sportsmen tend to be young, fit, world renowned and wealthy, and as such, it is no surprise that some women take a shining to male athletes. Furthermore, in the modern age athletes are essentially celebrities. They live under the microscope with their relationships, affairs and the like often being latched upon by the media and becoming widely reported news stories.

Just to clarify, let's establish what we mean by the term 'womanizer'. The Meriam-Webster dictionary defines a womanizer as a man who "pursues casual sexual relationships with multiple women", while the OED has a similar definition, but adds that the term is generally used to express disapproval.

Most of the sportsmen on this list are from the modern era, the vast majority being post-1970. This is due to the increased coverage of athletes relationships since that period and the media spotlight upon them, which simply didn't exist in the earlier days of professional sports, although some stories have inevitably emerged since. Here are the top 15 biggest womanizers in sports.

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15 Shawn Kemp

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From a young age Shawn Kemp was a serial womanizer. By the age of 28, Kemp had already fathered a confirmed seven children with six different women, with many believing that Kemp had even more children than that. Having left basketball in 2003, he spent the majority of his career with the Seattle Super Sonics as a power forward. Kemp, a six-time NBA All-Star, was arrested in possession of 60 grams of marijuana and a semiautomatic pistol in 2005.

14 Muhammad Ali

via dailymail.co.uk

Muhammad Ali's relationship details may be a little less well-told than some of the others, but one need only do a small amount of digging to see that the three-time world heavyweight champion was a real womanizer. In total, Ali has nine children - seven daughters and two sons - and has had four wives. His first marriage lasted less than 18 months. His second lasted 10 years, and saw the arrival of four of Ali's children. Two of Ali's nine children came from extramarital relationships. He is reported to have cheated on all his wives.

13 Dennis Rodman

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Dennis Rodman has certainly had a prolific sex life; he claims to have slept with over 2,000 women. The five-time NBA champion finds himself only in 13th place though because he also claims 500 weren't prostitutes. Rodman has openly stated that his relationships with prostitutes were as a result of his insecurities in his youth, and that his first sexual relationship was at the age of 20 with a stripper. He has had three wives and had a high-profile affair with singer Madonna.

12 Travis Henry

via thebostonjam.com

Former NFL running back Travis Henry played for the Buffalo Bills, Tennessee Titans and the Denver Broncos in a pro football career which lasted six years. Henry has 11 kids with 10 different women, tallying up to $170,000 a year in child support, which he was charged for not paying back in 2009. Like Kemp, Henry had all of his children before the age of 28. He married aged 19, to a 25-year-old, but the marriage was soon annulled. Now aged 36, Henry is currently engaged.

11 Radek Stepanek

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Along with Marat Safin, Radek Stepanek has long been considered the biggest womanizer in tennis. The Czech who now resides in Monte Carlo and is ranked number 22 in the world, having won five titles over the course of his career and earned over $10 million in winnings. Stepanek was engaged to Swiss tennis player Martina Hingis before their break up in 2007, he married fellow Czech player Nicole Vaidisova in 2010, but they divorced in 2013. More recently, Stepanek was dating another Czech tennis star in Wimbledon champion Petra Kvitova, but the pair separated after several months together.

10 Magic Johnson

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Three-time NBA MVP, Magic Johnson was renowned for his womanizing throughout much of his time in the NBA. For a number of years the former Lakers star was said to be sleeping with roughly 300 women a year, however, his world was turned upside down when Johnson contracted HIV. The disease forced him into an early retirement, and Johnson has campaigned for safe sex ever since. Johnson's HIV changed the way people thought in America, as the disease had once been considered a 'gay' disease. Johnson has since married and had a child who is not HIV positive.

9 Lenny Dykstra

via nbcwashington.com

Lenny Dykstra's womanizing past is a little darker than most on this list. In 1999, he was arrested for sexual harassment of a 17-year-old girl, although the charges were later dropped. In 2010, Dykstra was charged with writing bad checks to female escorts and adult film stars. In 2011, Dykstra's housekeeper accused him of forcing her to give him oral sex on Saturdays. The same year, he was charged with indecent exposure, after disrobing himself to potential personal assistants and telling them that the job required "massage services".

8 Antonio Cromartie

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New York Jets cornerback Antonio Cromartie signed a four-year deal worth $32 million with the Jets in March, after spending a year with the Arizona Cardinals, and Cromartie will need that money to pay his extortionate child support. The 31-year-old who was first drafted by the Cardinals back in 2006 has at least nine children with eight different women and was given a $500,000 advance by the Jets back in 2010 to help pay his child support. Cromartie married Candy Girls star Terricka Cason in 2010 and the pair have four children together.

7 Cristiano Ronaldo

via businessinsider.com

Record breaker Cristiano Ronaldo is now Real Madrid's all-time top scorer in La Liga, and will soon be their top scorer in all competitions, as well as now being the all-time top scorer in the Champions League, narrowly ahead of Lionel Messi. Worth an estimated $310 million and a heartthrob to many, Ronaldo has had a number of relationships over the years. He has dated English models Alice Goodwin and Gemma Atkinson, and Russian model Irina Shayk. Ronaldo's son was born in the U.S. in 2010, the identity of the child's mother remains unknown, with CR7 keeping his lips sealed. He is also rumored to have dated high-profile celebrities Kim Kardashian, Paris Hilton and Imogen Thomas.

6 John Daly

via news.com.au

It's probably fair to say that John Daly does not seem your archetypal womanizer. Certainly he is in stark contrast to the man above him, Cristiano Ronaldo, in terms of appearance, style and fitness at least. Yet that hasn't stopped Daly's serial womanizing. To date, he has had four wives, all of which have ended in divorce, often due to Daly fooling around with other women. One wife went as far as to install cameras in his tour bus to prevent any unfaithfulness, some indication of the trust in that relationship. In his autobiography, Daly talked of the numerous threesomes and groupies he had while on tour.

5 Derek Jeter

via thebiglead.com

New York Yankees legend Derek Jeter has had some of the most publicized relationships of any sportsman on the planet. The former MLB star who retired in 2014 as a five-time World Series champion has had at least nine widely-reported relationships. The women in question include Mariah Carey, Vida Guerra, Lara Dutta, Joy Enriquez, Vanessa Minnillo, Jordan Brewster, Hannah Davis and more. When Jeter wasn't busy with singers, models and former Miss Universes he was becoming the Yankees all-time career leader in hits.

4 Tiger Woods

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One of the greatest golfers of all time, Tiger Woods was the best paid athlete in the world for a number of years. Woods married Swedish model Elin Nordegren in October 2004, and the pair had two children together. In November 2009 it emerged that Woods may have been unfaithful to Nordegren, and in the coming months several women came forward as saying that they'd been sexually involved with the golfer. Eventually, Woods admitted his infidelity, confessing that he could have cheated on his wife with as many as 120 different women. The stories saw Woods lose billions in sponsorship and his form has never been as consistent since.

3 Alex Rodriguez

via totalprosports.com

New York Yankees star Alex Rodriguez is considered one of the greatest MLB players of all time. He married psychology graduate Cynthia Scurtis in 2002, but was constantly pictured with other women. In 2007 he had a more prolonged affair with an exotic dancer named Joslyn Morse, who refused to state whether the pair were having sex together at the time. A second high-profile case emerged in 2008 between Rodriguez and Madonna, and following this he and his wife divorced. In the aftermath of the split, a number of strippers and prostitutes emerged with their own stories of having slept with Rodriguez. He has since had a high-profile dating resume, including flings with Cameron Diaz, Kate Hudson and former WWE Diva Torrie Wilson.

2 George Best

Colorsport/Stewart Fraser

A style icon, the first genuine celebrity footballer and at one time the best paid footballer on the planet, it's little surprise that George Best is regarded as the ultimate "football playboy". His addictive personality with both women and alcohol were highly destructive, and Best once joked, "If I'd been ugly, you'd have never heard of Pele." He did go down as one of the game's all-time greats, but his time at the top was shorter than it should have been. He slept with countless women, including no fewer than four Miss Worlds, he once said, "I used to go missing a lot... Miss Canada, Miss United Kingdom, Miss World," but Best's most famous quote was, "I spent a lot of money on booze, birds and fast cars. The rest I just squandered."

1 Wilt Chamberlain

AP Photo/Paul Vathis

The most notorious and prolific womanizer in sports history has to be Wilt Chamberlain. Almost universally regarded as one of the NBA's greatest players of all time, Chamberlain holds records such as the only player to score more than 100 points in a single game, the only player to average more than 50 points in a season and the only player to average 30 points and 20 rebounds over their entire career. These achievements launched Chamberlain into superstardom.

He was a household name and one of the most recognizable faces in America as well as being supremely wealthy. This made it very easy for the already charismatic and charming Chamberlain to become a serial womanizer. His lawyer once commented that, "Some people collect stamps. Wilt collects women." He was good at it too, his friends once commented that Wilt once slept with 23 women in 10 days. It is alleged that he slept with 20,000 women, meaning that if he became sexually active at 15, he would have slept with more than one woman per day until his death at 63.

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