Top 15 NFL Stars Who Dated The Trashiest Celebrities

Status as a professional athlete brings one access to a whole new set of women. Specifically, the celebrity kind of women. It basically goes without saying that athletes have a far better shot at famo

Status as a professional athlete brings one access to a whole new set of women. Specifically, the celebrity kind of women. It basically goes without saying that athletes have a far better shot at famous women than the average dude. Athletes are fitter than average (at least) and have piles of money figuratively lying around, as even backups in the NFL are making a minimum of $450,000 per year in 2016. So the equation basically goes something like physical fitness plus a massive paycheck plus the confidence required to play professional sports equals a vastly improved chance at having a hot girlfriend or wife. This shouldn't be news to anyone.

Most of these women are great overall.  Looking around the NFL there are some great WAGs on every team and at every position. Actresses Olivia Munn and Kerry Washington are dating Aaron Rodgers and married to retired cornerback Nnamdi Asomugha respectively, and models Gisele Bundchen and Adriana Lima are married to and (possibly) dating New England Patriots Tom Brady and Julian Edelman. These are just four examples of women without catastrophic public personas who are dating football players.

On the other hand, there are plenty of celebrities who are complete headaches. Nightmares, train wrecks, dumpster fires, whatever you want to call them. They may be hot and rich, but the trashy label is not exclusive to the broke and the ugly. Whether they are just awful people, dreadful reality television stars or just drugged out party girls, here are the fifteen NFL players, both past and present, who have dated the trashiest celebrities.


15 Matt Nordgren - Lindsay Lohan


Recognize that name? Don't lie, you don't. Matt Nordgren played for the Texas Longhorns back from 2003 to 2005. He was on the Philadelphia Eagles practice squad in 2006, but was unable to continue his career due to injury. This was back in 2006. In 2013, a few different sources reported that he was dating everyone's favorite child-star-turned-drug-addled-mess, Lindsay Lohan.

After his NFL career, he worked in his family's business in the energy industry, started his own business, and had a couple of notable appearances on reality television. He and Lohan are broken up now, but according to sources, she was able to clean up significantly during their relationship, as he didn't drink around her ever. Good for her!

14 Tony Romo - Jessica Simpson


Does it really count as trashy if you're dumb? Well, in Jessica Simpson's case, yes, she is a trashy, dumb celebrity. Like with most of the ladies on this list, she's very much attractive and rich, but "dumber than a bag of hammers" is a phrase we aren't ashamed to use regarding this sharp cookie. Well, maybe that's a little too harsh. But hey, no one's really complaining all that much.

Tony Romo and Simpson dated between 2007 and 2009. During that time she was a pariah among Cowboys faithful as they blamed her for the losses of a few key games in which Romo played poorly. Romo eventually graduated from the blonde air head trope however and married stunning Texan Candice Crawford; a former Miss USA contestant and journalist.

13 David Binn - Pamela Anderson


If you've never seen the name David Binn before, you must not be a San Diego Chargers fan. Even if you are a Chargers fan, this name may not be a familiar one. He holds the record for most games played by a player for the team. He's also 34th in overall games played with 256. He was a linebacker and long snapper in college, but played only long snapper for the Chargers. He was with the team between 1994 and 2010, making the Pro Bowl in 2006 (who cares, he's a long snapper).

In 2007 and 2008, he was dating Pamela Anderson, who was once famous for bouncing around a beach on Baywatch. Some people still find her attractive, but really, she hasn't looked the same since 2000. Too much plastic surgery has rendered her looking like yet another Hollywood star all too eager to try their hand at slipping past father time. It was never gonna happen, but you can still try.

12 Derrick Ward - Khloe Kardashian

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Now retired, Derrick Ward was drafted by the New York Jets in the 7th round of the 2004 Draft. He was released later that year and the running back got picked up by the New York Giants, with whom he spent five seasons. He won a Super Bowl with the Giants in 2008. From 2009 through 2011 he played for the Buccaneers and Texans but retired in 2012. While he had a few decent seasons with the Giants, he was always a member of a committee with the team.

Back in 2009, he was spotted with Khloe Kardashian, the second oldest of that annoying clan. For those who know their sports, but not their reality TV personalities, this is the Kardashian who drove Lamar Odom to the point of insanity. We can't verify this absolutely, but we'd imagine that having any involvement with any member of that family - regardless of what you read in People - would drive almost any man to drink and whatever other juvenile miscreant behaviour. We don't know how Kanye has held up this long.

11 Miles Austin - Kim Kardashian


Now 32 years old and a veteran of ten NFL seasons, Miles Austin is a free agent and it looks unlikely that he will be getting signed anytime soon. But with two Pro Bowl appearances, three 100+ catch seasons, two seasons over 1,000 yards, and leading the NFC in receiving yards in 2009, he left it all on the field. His 250 receiving yard game back in 2009 still stands as a Dallas Cowboys record.

In 2010, he briefly dated Kim Kardashian. She is a reality television "personality" who, like her sister Khloe (who we saw above), is a product of what's either the general dumbing down of the general public or the most elaborate prank in history, who has made a lot of money doing very little. Well the whole thing didn't last very long (shocker) and soon went belly up - much like Austin's career.

10 Reggie Bush - Kim Kardashian

One of the most exciting dual-threat running backs of the last decade, Reggie Bush has had quite a career, which includes four 1,000+ yard seasons (from scrimmage), an All-Pro season, and a Super Bowl ring earned with the New Orleans Saints. He contributed to that game with nine touches (five rushes and four catches) for a total of 63 yards. Since his time with the Saints, he saw an increase in work while playing for the Miami Dolphins and Detroit Lions between 2011 and 2013.

From 2007 until 2010, he dated reality television star Kim Kardashian. We've already heard enough about her, let's move on. But seriously, this might have been one of the biggest events in Bush's career, and it had nothing to do with football whatsoever. Just goes to show how easily those Hollywood-types can suck you in.

9 Jeremy Shockey - Tara Reid


Spoiler alert, there are a few football players who have dated Tara Reid. They dated her before she started to look... let's just say how she looks now. She's aged pretty harshly and surgery has rendered her chest and stomach area looking...wrong. There's no other way to put it.

For those with short memories (or who didn't follow football from 2002-2011), Jeremy Shockey was one of the best tight ends of the 2000s. Playing between 2002 and 2011, he was selected to four Pro Bowls, won two Super Bowls (one with the New York Giants and another with the New Orleans Saints) and finished his career with a very respectable 6,143 receiving yards. He dated Tara Reid very briefly back in 2002, when she was just a trashy party girl, but before she became a trashy former party girl with a body that was destroyed by medical science.

8 Kyle Boller - Tara Reid


Reaching deep into the lengthy list of useless first round quarterbacks, here is Kyle Boller, selected by the Baltimore Ravens in the first round of the 2003 NFL Draft. He showed signs of greatness from time to time, lighting up the Green Bay Packers in 2005, for example, but between those brief flashes of greatness was a lot of garbage and usually more interceptions than touchdowns, amplified by very low completion percentages.

He retired in 2012 after a few seasons of backup work. Back in 2010, he married a former Miss California by the name of Carrie Prejean. Long ago, however, he was not a man of such distinguished tastes and briefly dated Tara Reid in 2004. The relationship was relatively low key. Had Boller been a more successful player, the media would've at least given the two the light of day.

7 Matt Leinart - Paris Hilton


From the extensive database of the all time catastrophic NFL draft choices, Matt Leinart won the 2004 Heisman Trophy while with the USC Trojans and was drafted tenth overall in 2006 by the Arizona Cardinals. His time in Arizona was unremarkable at best and he did not play a full season between 2006 and 2009, while with the team. He played backup and on some practice squads until 2013 at which point he accepted what the football world was trying to tell him.

His dating resume includes the once (somewhat?) relevant Paris Hilton. The two dated back in 2006, back when Hilton's fame was around its apex and when Leinart was still considered to have the potential to be an elite NFL quarterback. It was a short fling that soon after fizzled out, much like both Leinart and Hilton's careers.

6 Tom Brady - Britney Spears /

We should clarify on this one, Tom Terrific does not date exclusively trashy women. Quite the contrary. Among his exes is the stunning actress Bridget Moynahan and he's currently married to one of the most famous (and beautiful) models of our time; Gisele Bundchen. However, he very briefly dated singer-turned trainwreck Britney Spears - if only for a while.

He dated Britney for a brief period in 2002 (before her meltdown), but nothing really came from it. Just like most relationships among celebrities, this was nothing but a short fling. Their paths would divulge greatly from that point on, both in terms of their dating lives and careers. Brady would marry his model wife and establish himself as an all-time great, while Spears would eventually marry, divorce and then completely freaking loose it.

5 Rashad Butler - Mya G


Rashad Butler, a now-retired offensive tackle, was drafted by the Carolina Panthers in 2006, but didn't play much throughout his career. Underweight in his early seasons, the doctor for the Houston Texans (who picked him up after the Panthers cut him) discovered he had ulcerative colitis; a nasty rectal disease that causes weight loss and abdominal pain, a potential death sentence for a lineman's career.

Off the field, however, things went somewhat better. Butler's girlfriend was Mya G. That's her stage name, we couldn't find her real name. She was (is?) an adult entertainer and the two apparently split up back in 2011 after some rumours of infidelity on Butler's part.

4 Tanard Jackson - Jemini /

Former NFL safety Tanard Jackson was taken in the fourth round of the 2007 NFL Draft by the Tampa Bay Buccaneers. He started every game of his first two seasons and twelve in his third before being suspended by the league for a substance abuse violation. He missed most of the next season for a second violation. He would return to the league but was ultimately suspended two more times for similar things. He is currently under indefinite suspension and will likely not play football again.

He also dated an adult film star, who went by the name of Jemini. Before his suspension in 2010, he started a relationship with her and the two ended up having a kid. Apparently the relationship became terrible because a couple of years ago she was arrested for prostitution after Jackson didn't pay his child support.

3 Al Cowlings - Devon Shire

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Now there's a name you don't see every day. Al Cowlings played linebacker from 1970 until 1979. He first played for the Buffalo Bills, and then for the Houston Oilers, Los Angeles Rams, Seattle Seahawks, and finally the San Francisco 49ers. He played much of his early career with O.J. Simpson and would play on two NFL rosters with him as well. He was a key figure in the capture of Simpson in 1994 and was the driver of that infamous white Ford Bronco.

During Juice's murder trial, Jennifer Peace (whose entertainment name was Devon Shire) infamously said that Cowlings had told her all of the details of the murder, as the two had dated briefly and he allegedly ran his mouth about the exploits of his boy OJ. A year later, Devon Shire would come into the headlines again, alleging that MLB slugger Barry Bonds had knocked her up. Wow.

2 Hank Baskett - Kendra Wilkinson

Remember Hank Baskett? If you do then well done, we admire your memory of monumentally subpar wide receivers. He was signed to the Minnesota Vikings in 2006 after not being taken in the draft. He was traded to the Eagles during that offseason, played three seasons there before splitting 2009 between the Eagles and Colts. He spent 2010 and part of 2011 floating around the league, but basically retired after the 2010 season.

In 2009, he married Kendra Wilkinson. Don't get us wrong, she's a stunning woman, but her former occupation is concerning. She was one of Hugh Hefner's live-in girlfriends from 2004 until 2008. Since then she has had a couple of reality TV shows. Remember that abstinence nonsense from health class, that says when you sleep with someone, you're sleeping with everyone they've slept with? We have to wonder if Baskett thinks about during the immense amount of free time he's had since his NFL career tanked.

1 Brian Urlacher - Jenny McCarthy 


The retired Chicago Bears linebacker is arguably the third best middle linebacker of the 2000s. Ray Lewis and the late Junior Seau probably have him beat, but beyond that there is nobody else. The eight-time Pro Bowl selection and four-time All-Pro was a tackling machine and a top-tier locker room leader. Off the field, however, he has dated one of the trashiest celebrities out there.

He was divorced from his wife Laurie in 2003 and somehow ended up with professional crazy person and confused medical expert Jenny McCarthy somewhere along the way. They don't get much trashier than Jenny McCarthy. Don't get us wrong, she's beautiful, but Urlacher could have done so much better. He also had an on and off relationship with Jennipher "way to spell that first name" Frost, who was a contestant on America's Next Top Model." The two married. She seems nice.

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Top 15 NFL Stars Who Dated The Trashiest Celebrities