The 20 Biggest Playboys in Sports History

Image via Complex Original

Famous alleged flings: Bar Rafaeli, Arielle Vandenberg, Summer Spiro

Shaun White is extreme sports' biggest star and has grown up in the sport into a charismatic icon that kids can look up to and women adore. We bet you didn't know how much women adore White though, he actually managed to bag supermodel Bar Rafaeli along with actress Arielle Vandenberg. Respect Mr. White, much respect.

Famous (alleged) WAGs: Carolina Marcialis, Rosaria Cannavo, Stefania Orlando

Before Balotelli burst on the scene, Antonio Cassano was the Italian striker with an eye for beautiful women. He's a solid player but is even better off the pitch and maintained relationships with a few foreign beauties during his time with Roma and Real Madrid, among other clubs.

Famous (alleged) WAGs: Susana Werner, Milene Domingues, Daniela Cicarelli, Maria Beatriz Antony

Before Cristiano arrived, there was one Ronaldo and he was the king of the football world. Naturally a king would be appeased with his choice of women, and Ronaldo had just that as he was with numerous models and actresses before that whole tranny incident. The tarnish from that story may still hold some weight for many fans, but without a doubt Ronaldo was one of the bigger playboys of his time.

Famous (alleged) WAGs: Rihanna, Tahiry Jose, K. Michelle, Britanie Girard

The 2012-13 Sixth Man of the Year is a free spirit who seems to be all about enjoying life and getting his on and off the court. Since joining the Knicks, J.R. has quite recklessly gotten with reality stars K. Michelle and Tahiry Jose, and has been linked to Rihanna. When he tweets stuff like this about some famous tail he's gotten, we anxiously await his next celebrity fling.

Famous (alleged) WAGs: Kim Kardashian, Amber Rose, Melissa Molinaro, Eve Torres, Claudia Sampedro, Mayra Veronica

Reggie Bush is as much a ladies man as he is an explosive playmaker on the field. We all remember the heavily publicised on and off relationship with Kim Kardashian, but some of us forget the Amber Rose hookup that ends up being quite ironic now that we have Kimye. At any rate, Bush has nothing to be ashamed of for his work off the field, bravo former Heisman winner, bravo.

Famous (alleged) WAGs: Elisha Cuthbert, Hilary Rhoda, Rachel Hunter

One of the most hated and scrutinized hockey players of recent memory, Sean Avery had the game to warrant dudes wanting his sloppy seconds. Avery was linked to actresses Elisha Cuthbert (the subject of his sloppy seconds comment), model/actress Rachel Hunter, and most recently model Hilary Rhoda. He'll forever be known as one of hockey's assholes, but the respect he gains from his blackbook almost seems to make up for it.

Famous (alleged) WAGs: Rihanna, Letoya Luckett

After the Chris Brown incident, Rihanna's first and only real public relationship since has been with Dodgers slugger Matt Kemp. For a fair amount of time Kemp was all over the blogs for being the guy who bagged Rihanna, but what many don't know is that he was also linked to former Destiny Child singer Letoya Luckett back in 2010. Yup, we're jelly.

Famous (alleged) WAGs: Erin Andrews, Paulina Gretzky, Rachel Hunter, Katie Cassidy

Jarret Stoll is certainly no Alexander Ovechkin or Sidney Crosby but his dating track record keeps him in the tabloids. First off, this year he bagged one of the most sought after ladies in sports media in Erin Andrews. Who was he dating the year before that? None other than Paulina Gretzky. The rumors of him dating The Great One's daughter came after he helped bring a Stanley Cup to L.A. in 2012. Girls love a guy who know how to handle the...alright, we'll stop there and keep things classy.

Famous (alleged) WAGs: Marilyn Monroe, Dorothy Arnold, Lee Meriweather

DiMaggio wasn't the best looking dude, but with his immense talent (nine World Series rings and three AL MVPs, anyone?) and ultra smooth demeanor he managed to do pretty darn well with the ladies. Most famously he eloped with Marilyn Monroe, arguably the biggest sex symbol ever. Joe D. also was with other actresses however, as he managed to work his way through the New York socialite scene.

Famous (alleged) WAGs: Elin Nordegren, Lindsey Vonn, Rachel Uchitel

Here's one thats not up for debate. In case you were under a rock for the last five years, you know Tiger has had no problem finding women. Granted, he was married for the lion's share of the time, but the fact remains that Woods is a playboy. His infedelity and the subsequent sex scandal ultimately led to a $110-million divorce settlement with Elin Nordegren. Woods rebounded earlier this year when his relationship with Lindsey Vonne became public. Ambien-laced sexcapades with cocktail waitresses? Don't hate the playa, hate the game.

Famous (alleged) WAGs: Kate Upton, Eva Longoria, Hilary Rhoda, Jamie-Lynn Sigler

Mark Sanchez is the complete opposite off the field as he is on the field. When he's laced up he's a mistake prone signal-caller, while off the field he's damn near a god. The Sanchize has done his thing when it comes to lovely ladies. He's been associated with Eva Longoria, and everybody's favorite young model Kate Upton before Verlander was in the picture. New York fans have one thing to be proud of him for.

Famous (alleged) WAGs: Gisele Bundchen, Bridget Moynahan, Tara Reid

Another example of somebody just winning at life, Tom Brady does his thing on and off the field to the tune of a blackbook boasting actresses and models. We all know about his current ride or die wife Brazilian model Gisele Bundchen, but some forget his past relationship with baby mommma Bridget Moynahan and rumors of a fling with Tara Reid. Could Tom Brady partly be the cause of the Tara Reid trainwreck once he dumped her?

Famous (alleged) WAGs: Suzy Miller, Sarah Lomax

James Hunt was England's very own eccentric race car driving playboy throughout most of the '70s. He wasn't Wilt Chamerlain, but rumors say he had been with 5,000 women before passing away of a heart attack at the age of 45 in 1993. Extensive drug and alcohol use may have put a tarnish on his legacy, but Hunt will forever go down as one of that time period's biggest playboys.

Famous (alleged) WAGs: Angela MacDonald, Alex Pursey

The Irish footballer made waves in the '70s for his wild lifestyle, owning his own nightclub and routinely partaking in a night out or two. Married twice, Best never seemed to really be able to settle down even incurring domestic violence charges through out the tumultuous latter half of his career. Due to his lavish lifestyle, though, women were never far from Best and he always accomodated the ladies in his life accordingly.

Famous (alleged) WAGs: Madonna, Torrie Wilson, Kate Hudson, Cameron Diaz

There's not a lot that's gone right for A-Rod recently. He's gotten himself in trouble for PEDs yet again, got beamed by an opposing pitcher, and pretty much everybody who's anybody has something negative to say about him. His saving grace throughout the highs and lows of his career? Beautiful blondes like Torrie Wilson and Kate Hudson seemingly being into multimillionare athletes. Surprise, surprise. Oh and A-Rod has the balls the size of craters for trying to bag fans at a playoff game. So right yet so wrong.

Famous (alleged) WAGs: Fanny Neguesha, Raffaella Fico, Sophia Reade, Dayane Mello

Still only 23 years of age, Super Mario has put in his fair share of playboy work since he hit it big. The Italian football star has been linked to models Raffealla Fico and Fanny Neguesha (whom he's currently engaged to) along with lesser-known women as he's progressed into the party animal we've all grown to love.

Famous (alleged) WAGs: Randi Oakes, Mamie Van Doren, Phyllis Davis

Broadway Joe was a bad man on the field, but he might've had an even bigger impact off it. One of the first NFL players to have the charisma and pizazz, Namath had an enormous amount of swag for his time. As to be expected with his personality, Namath scored with women off the field nearly as much as he did on. Respect it, Sanchize. Let's leave the Suzie Kolbert incident out of this.

Famous (alleged) flings: Irina Shayk, Paris Hilton, Nereida Gallardo, Luana Belletti, Gemma Atkinson

No shame in Cristiano Ronaldo's game. He's with a new chick nearly everytime we see him and he's always rocking that trademark smile. Models, actresses, and frankly any hot girl in his vicinity will probably end up with CR7. Though he's engaged to model Iriana Shayk, his track record is extensive.

Famous (alleged) flings: Annette Tannander, Lynda Huey, Kim Novak, etc.

There are two numbers Wilt Chamberlain's known for: 100 for the amount of points he managed to score in one game, and 20,000 for the amount of women he claimed to have sex with. Yep you read that right, 20,000. Wilt's sexual escapades are the stuff of legend and he will forever go down as one of the biggest playboy athletes ever.

Famous (alleged) WAGs: Minka Kelly, Jessica Biel, Jessica Alba, Vanessa Minnillo, Mariah Carey, 

The GOAT when it comes to playboy athletes, Jeter sets the precedent for quality and quantity. There's no surprise that young dudes like Matt Harvey openly look at him as the model. The Captain has been rumored to even leave his one night stands goody bags with autographed gear. Game over.