20 Athletes Who Dated The Trashiest Celebrities

Relationships for athletes come and go. They most always come out to the media one way or another especially today with social media. Sometimes relationships happen with an athlete and celebrity just for gossip and rumors other times its legit. We have seen a lot of  athletes go out with a celebrity then break up with one to go out with another celebrity. For example the Kardashian sisters like Khloe and Kim seem to go from one athlete to another at one point in their life just to make the news and gossip.

When Tony Romo dated Jessica Simpson that was a mistake waiting to happen. It also causes a rift in the locker rooms too if the athlete is in the news for the wrong reasons and it stems from the relationship the athlete is in.

In this article I will name the top 20 athletes who dated trashy celebrities at one point in their careers. Sometimes it works out but mostly all the time something happens to ruin it and it gets out in the news and social media. Sometimes you wonder why the athletes get themselves in these relationships, but those are questions that really can't be answered.


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Tony Romo and Jessica Simpson dated from 2007-2009. She was a curse to the Cowboys fans as they would blame her for their losses and if Romo played poorly. Romo kissed Simpson on the first date. Jessica began telling people at the time "The fact that this guy, on our first date, in the first 10 minutes of dinner, wanted to lean over the table and say, ‘This is my girl and I want to kiss her’ – our first kiss in front of everybody – was awesome." Jessica Simpson may be a beautiful blonde on the outside but inside she is anything but. Romo would move on to bigger and better things and marry Candice Crawford who is a former Miss USA contestant and journalist.


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Dating any Kardashian is bad news and annoying. In 2009 Derrick Ward was spotted with Khloe, who is the second oldest. Derrick Ward was drafted by the New York Jets in the seventh round of the 2004 NFL Draft. He was later released and picked up by the New York Giants later that season. He won one Super Bowl with the Giants in 2008 when they defeated the Patriots. He also played for the Tampa Bay Buccaneers and the Houston Texans before retiring in 2012.

Dating any Kardashian has to drive any man crazy and insane for how much drama they must take in. It's a wonder how Ward didn't let it cause a distraction in the locker room when he was playing for the Giants.


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Miles Austin was a former pro football wide receiver who played for 10 seasons in the NFL. He had 5,273 yards, 37 touchdowns, and 361 receptions. He spent eight seasons with the Cowboys and one season each with the Browns and the Eagles. For a short while he dated Kim Kardashian in 2010 which like Khloe is another annoying celebrity who just loves drama and gossip. They split because of the distance and Kim was filming her TV show Keeping Up With The Kardashian's was too much. Before Kim left for Europe they ended the relationship. Much like Austin career it didn't last and Kim would move on to other athletes and celebrities. As for Miles Austin he would marry Stacy Sydlo in 2014.


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Reggie Bush was one of the best running backs in the game for a brief period of time. He had 5,490 yards 36 touchdowns, and four seasons with 1,000+ yards. He also has a Super Bowl ring from the New Orleans Saints. He played for five seasons with the Saints, two with the Lions, two with the Dolphins, one season with the Bills, and San Francisco 49ers.

From 2007- 2010 however he dated Kim Kardashian, who again like I've said has seemingly dated every athlete and celebrity under the sun. Of course the relationship didn't last and was just made for news and drama that again that family loves. That's how they make their money by making up drama. Some people call it the 'Kardashian Curse'.


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Matt Leinart was drafted tenth overall in 2006 by the Arizona Cardinals.  He won the 2004 Heisman Trophy while with the USC Trojans. His time in Arizona was not impressive at all. He had 15 touchdowns and 21 interceptions in his NFL career. All that hype after him winning the Heisman Trophy meant nothing once he was in the National Football League. He also played one season with the Houston Texans and one season with the Oakland Raiders.

Back in 2006 however he was rumored to have dated Paris Hilton, back when he was supposed to be an elite quarterback in the NFL and she was still a big name. However the relationship was cut short much like Leinart's time in the NFL.


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This next one was never really going to work out. In the end it worked best for both of them. In 2002 for a short period of time Tom Brady dated Brittney Spears and this was before she completely lost herself. They would separate because their careers were taking different paths and it wasn't going to work out in the end. Tom would then be one of the greatest quarterbacks of all time and win five Super Bowls. Brittney Spears has completely lost herself and goes from one relationship to another.

If Tom was still with Spears he probably wouldn't be on the Patriots. It would be too much of a distraction, so it's a good thing they split. Tom now is married to Gisele Bundchen with three children, with one of the children being from Bridget Moynahan.


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Now retired Chicago Bears linebacker was probably the best at his position in the 2000s. He went to the Pro Bowl eight times and was a four-time All Pro selection. he had 41 sacks, and 1,040 tackles in his NFL career. Off the field he had his trouble with finding a decent woman. Jenny McCarthy kept her relationship with Urlacher quiet till they broke up telling People at the time 2012 saying "Brian and I have decided to turn our romance into an amazing friendship, I will continue to be the biggest cheerleader for him. Go, Bears!” Urlacher has three children from past relationships and this particular one was short lived. He's doing well for himself nowadays, as he recently got married to former America's Next Top Model contestant Jennipher Frost.

13 KEVIN DURANT And Brittney Elena

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Kevin Durant just earned his first NBA Championship ring this past season when he went to the Golden State Warriors.  He left the Oklahoma City Thunder and Russell Westbrook to join Steph Curry and the Warriors so he could have a better shot at winning an NBA Championship. His wishes came true on the court but  off the court he has trouble finding the right woman. In March of this year it was reported he was dating Brittney Elena, from former Wild’n Out Girl show. She is also a also a TV correspondent and she is also trying to improve her basketball game trying to be just like Kevin. They reportedly started dating at the beginning of last season. It was last known he was dating Jasmine Shine back in June so that relationship with Brittney Elena was short lived.

12 DEANDRE JORDAN And Meghan Trainer (And Amber Alvarez)

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DeAndre Jordan is a great basketball player on the court for the Los Angeles Clippers but off the court he has his trouble with woman. He had been linked to singer Meghan Trainor but she would be tight lipped on it telling ET at the time "DeAndre is a great friend of mine. He’s awesome.” He also was dating Amber Alvarez for two years and as of June of 2016 it was reported they "worked through" the issues. At the time he was dating her he had a baby with another girl named Ashley. Very much a player off the court as well, Jordan is. Alvarez's modeling gigs often call for her to pose provocatively, but Jordan doesn't seem to mind.

11 KYRIE IRVING And Kehlani Parrish

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The former Cleveland Cavalier and current Boston Celtic has also had his time with woman. He dated Kehlani Parrish, who is an R&aB singer. Parish also posted a picture of herself connected to an IV, implying that she attempting to commit suicide. Irving would send out a series of four Tweets according to the New York Daily News saying. "It's unfortunate that it's received so much attention but it's become bigger because of a post that was misunderstood. It's been hard to see what's been going on and not address the truth. I do not justify the picture of what dude did to try to spark all of this nonsense that could have been avoided, Me and Kehlani were not dating when the picture came out."

Irving now is trying to make a name for himself on the Boston Celtics. Hopefully that means he will attract a higher class of women.


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Former NBA superstar Amar'e Stoudemire was a great player in the NBA. He played 15 seasons in the league for the Phoenix Suns, New York Knicks, Miami Heat, and Dallas Mavericks. But off the court he had his time with women. Before Ciara landed in Russell Wilson's lap she dated Amar'e Stoudemire in 2011. She didn't mind showing her bad side while dating Amare Stoudemire at the time. The relationship didn't last long.

It was reported that Stoudemire was seeing another woman named Amber Rose who he broke up with for Ciara according to K97.5 Stoudemire would go on to marry Alexis Welch, and have four children with her. Ciara would then marry Seattle Seahawks quarterback Russell Wilson in 2016.


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Odell Beckham Jr. Is currently on the IR for the New York Giants. In his four seasons with the Giants he has 4,424 yards and 38 touchdowns. He has recently made the news for the wrong reasons like partying last year on a boat, and this season for peeing like a dog after scoring a touchdown.

At a party at Drake's, house pictures were taken of Beckham and Kardashian flirting. It came out that the two were dating but both shot down the rumors. Kardashian is a drama gossip bag and Beckham cares more about the high life than actually performing on the field. Beckham said of the party "We were in the kitchen of the house, where there was only 15 people. It’s just kind of like … ‘dating?’ I just met this person. This is maybe the second conversation we’ve had."  Either way it was very short lived.

8 MATT KEMP And Rihanna

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Matt Kemp has played 12 seasons in Major League Baseball. He played for the Dodgers, Padres, and is currently with the Atlanta Braves. He has 1,634 hits, 259 home runs 920 RBIs and a .285 batting average in his career. Kemp is also an two time All Star two time Gold Glove winner, and a two time Silver Slugger. In 2011 he and Rihanna broke up after dating for a year. Rihanna told BET at the time "I just let it go. I don't ever want to have to depend on a relationship, I think it’s a really special thing to find love. It’s beautiful. Nothing can match it. But I want to make sure I find other things in life that I love—besides love.” Rihanna would then get herself wrapped up in the Chris Brown scandal.

7 ALEX RODRIGUEZ And Cameron Diaz

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Cameron Diaz and Alex Rodriguez both have had great careers. While it's debatable as to who has had the more successful professional career, it's hard to argue with A-Rod's dating resume. Rodriguez is currently dating Jennifer Lopez and an analyst for Fox Sports during the MLB Postseason. During the 2011 season Rodriguez and Cameron Diaz broke up probably because their career paths were taking different turns. Diaz was in many raunchy movies and for Rodriguez, he was trying to make a name for himself again.

Sources told People at the time “They are broken up right now, They are still very close. There was always a certain magic between them. They’re still close friends and will continue to be close friends. They have considerable respect for each other.”


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Nick Young was dating Iggy Azaleah when he was a player for the  Los Angeles Lakers.  D'Angelo Russell recorded Young talking about cheating on his girlfriend and it got out. In today's social media nothing is secret; everything gets out today. Azalea saw the video and tweeted after seeing it " Hmmm I see D'Angelo Russell is trending… I actually liked his film. Thanks bro.”

She would also break up with Young because she told People "I broke up with Nick because I found out he had brought other women into our home while I was away and caught them on the security footage." Nick Young now plays currently for the Golden State Warriors. If anything, he looked like the trashier one here.


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Lamar Odom is another example of having the Kardashian curse him with her had just bad written all over it. They divorced in 2016 and he  told Wendy Williams at the time when asked if they would get back together "no."I say that with no offense to her—that would be the best for both of us you, know what I'm saying? We have to keep our distance." Odom was also doing drugs such as cocaine while playing basketball and while being with Kardashian. He told US Magazine just this past summer "(I) was doing coke every day. Pretty much every second of free time that I had, I was doing coke. I couldn’t control it. I didn’t want to control it.” The relationship between him and Khloe is long gone for now and probably forever.

4 DEVIN HARRIS And Meghan Allen

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The veteran guard has played 16 seasons in the NBA. He started his career with the Dallas Mavericks and has returned. He also played  for the Nets, Utah Jazz, and the Atlanta Hawks. He's played over 800 games in his career and a one time All-Star. Harris and Playboy Cyber Girl Meghan Allen started dating when he was playing for the New Jersey Nets at the time. It didn't cause a distraction for him on the court and I'm sure she got the eye when she would go to games. They married in 2013. Harris has been able to stick around in the NBA for a long time and he mostly keeps his married life private, which is something that's very difficult to do nowadays.


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Dennis Rodman is a National Basketball Hall Of Famer. He was inducted in 2011. Off the court however he was dating Madonna for a time and it was reported she wanted to have his baby. This was before Madonna became a classier woman and was in her wild days.

In his 1997 book, As Bad As I Wanna Be, Rodman wrote " She wanted to get pregnant really bad, She would send me faxes that said, 'I really want to be with you, I miss you. I want I want to have your baby.' Sounds like a complete nut job if you ask me. And why Rodman would reveal that personal and private information is just weird.

She even flew from Las Vegas to New York City just to have sex with him. Rodman was also briefly married to Carmen Electra back in the late 90s.


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Quentin Richardson played for five NBA teams during his 13- year career. He played for the Los Angeles  Clippers, New York Knicks, Orlando Magic, Miami Heat and the  Phoenix Suns He played in 783 games. He is married to Miya Manuel, wedding her back in 2012. NBA players Shawn Marion, Dorell Wright, Trevor Ariza and Dwyane Wade were in attendance. With him being on so many different teams he as dated a bunch of different women before finding the one for him. From the west coast to the east coast that's a lot of woman. Richardson’s dated slightly younger, and slightly older women. He once dated  actress Regina King, who was 10 years older. Let's hope he's now settled down for good.

1 KRIS HUMPHRIES And Kim Kardashian

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The Kris Humphries/Kim Kardashian drama had mistake written all over it. Anything to do with that family you know your in for drama misery and gossip. Kim Kardashian was cheating on Humphries with Kayne West which is why she didn't invite him to their wedding. They got married in August of 2011 and filed for divorce 72 days later. The $10 million wedding they had went right out the window. The sad thing too is that Kardashian knew the marriage was a bust by the honeymoon.

Kim knew Kris wasn't the one for her the second they moved in together after the wedding. So why get married? For media attention drama and gossip. That's what that family is all about. Let's hope athletes are careful about who they hook up with going forward.. who are we kidding, that won't happen.

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