Trading Up: The 10 Athletes Who Did It Best

Trading in your wife or girlfriend for an impressive upgrade is an unalienable right of the American professional athlete protected by the Constitution (just trust me, I was a history major).  As a woman, I can’t say that I love this practice, but there are plenty of things that I dislike more—like bugs and daylight savings time.

Being in a relationship with even the most mediocre of pro-athletes (hello Kyle Boller!) comes with endless perks—money, fame, access and living the dream of making all those girls you went to high school jealous.  Unfortunately, it also means that you are in a daily competition to keep him in your bed because every skanky broad across the country wants to make all the girls they went to high school with jealous too.

This process doesn't always involve cheating, violence and/or tabloid humiliation; sometimes it just means quietly dumping a nice lady because you’re "not ready for marriage," and then marrying a model a few months later. No matter the circumstances—you’d be hard pressed to find a famous athlete physically “trading down” after a breakup or divorce.   

These are 10 athletes who have mastered the art of trading-up, starting at No. 10 and working down to the most impressive trade-up of all time. 

Kyle Boller: Tara Reid for Carrie Prejean

Combine workout wonder and subsequent NFL dud Kyle Boller barely qualifies as a professional athlete. His “career” peaked during his rookie season in 2003 and then began a slow and painful seven-year descent into obscurity, leaving Brian Billick’s coaching career dead in its wake—so, not all bad news! 

In 2004, Boller made headlines when he took his turn on the proverbial neighborhood bike, and sometimes actress,Tara Reid. Eventually, he sobered up and went in search of his upgrade. 

In 2010 he "opposite-married" noted solo sex tape enthusiast and moral crusader, former Miss California Carrie Prejean. Frankly, I’d rather hang with Tara Reid, but Prejean is smokin’ hot and probably didn’t show up to their wedding clutching a half-empty bottle of champagne with her panties around her ankles, so she's a definite upgrade.

Tony Romo: Jessica Simpson for Candice Crawford

Tony Romo became Jessica Simpson’s FBD in late 2007—I distinctly recall the rabid Steelers fan in me coming together with the celebrity gossip enthusiast in me, and thinking “this is going to be good”—and good it was. 

Their relationship was tabloid fodder from day one thanks to the cranially-vacant Simpson’s well-known penitent for “oversharing” details of her private life. 

Eventually the two split, though the details are hazy—reports suggest that Romo and Simpson ended their relationship in summer 2009, and Romo and former Miss Missouri Candice Crawford began their relationship in summer 2009. 

You do the math, thankfully Simpson can't.

Romo put a ring on it in late May 2011, and much like wedding guests at the Romo wedding, I'm sure Jessica Simpson, currently engaged to Eric Johnson, couldn’t be happier for the newlyweds.

Jeff Garcia: Kristen Hine for Carmella DeCesare

NFL journeyman quarterback Jeff Garcia is most famous for being the first in a long line of patsies who eventually incurred the ire of infamous rabble-rouser Terrell Owens.  In a story that would repeat itself throughout T.O’s career, their relationship was strained, but as you know, there are two sides to every story. 

Owens felt the problem was that he was always open and Garcia, who connected with T.O. on exactly half of his 32 touchdown passes in 2001, was deliberately trying to quell his greatness…that and the fact that he felt Garcia was gay.  

Garcia felt (and I’m taking liberties) the problem was that T.O. was an overrated lunatic who was an annoying person. He also defended his sexuality in a public statement.

Garcia immediately responded by simultaneously beginning a relationship with 2004 Playboy Playmate of the Year, Carmella DeCesare and Cleveland townie, Kristin Hine. 

How the two found out about each other is anybody’s guess (my guess is that Garcia accidentally spilled the beans over wine coolers)—all we know for sure is Garcia took Decesare out to a club where they ran into Hine, and while at the club, Decesare allegedly drop-kicked Hine in the head, winning the hand of Garcia in marriage.

The headlines all read something along the lines of “Accused Homosexual Jeff Garcia Has Women Fighting Over Him—Obviously Not Gay."

Well played Garcia, well played.

Jason Kidd: Joumana Kidd for Porschla Coleman

In 2007 Jason Kidd filed for divorce from Joumana Kidd, his wife of 10 years and mother of his three children, citing “extreme cruelty” throughout their marriage as the reason.  The pair had a rocky relationship and exchanged mutual “crazy” accusations over the years and throughout their divorce. 

Kidd rebounded (heh) with 2009 April Playboy Playmate of the month, model Hope Dworacyk, before moving on to current fiancé and baby mama Porschla Coleman. 

Kidd and Coleman are currently engaged and plan to marry in 2011. 

Dwyane Wade: Siohvaughn Funches for Gabrielle Union

High school sweethearts Dwyane and Siohvaughn married in 2002, had two children, and then divorced in 2007. 

The divorce was messy, to say the least—Wade was rumored to have cheated with singer Kelly Rowland and Jason Kidd’s jilted high school sweetheart, actress Gabrielle Union, Wade’s current girlfriend.  Funches did not take it well, suing Union for causing her and her sons' emotional distress and accusing D-Wade of exposing her to STD’s and abusing her and her sons. 

Who knows or cares if any of this crap has been resolved, but in March 2011, Wade was awarded sole custody of his kids and Funches, who went through as many as nine divorce lawyers, is likely plotting something scary.

Jeff Gordon: Brooke Sealey for Ingrid Vandebosch

Jeff Gordon, the only NASCAR driver recognizable by the general public, married Brooke Sealey in 1994 two years after they met at a race and eventually divorced nearly a decade later.

The approximate time line is: In 2002, Gordon was introduced to model Ingrid Vandebosch by a mutual friend, in late 2002, Gordon filed for divorced from Sealey, in 2003 Gordon and Vandebosch began “officially” dating and were eventually married in November 2006—the couple are currently expecting their second child.

I don’t know anything about NASCAR, Jeff Gordon, or his ladies, but through some research, I noticed that Wonder Boy’s career has been absolutely in the toilet since 2002.  I’m not saying it’s karma...but I’m not, not saying that.

Michael Jordan: Juanita Jordan for Yvette Prieto

In 2007, Air Jordan taught us all that there are more important things in life than money, like banging models (Booya!), when he announced his divorce from wife of 17 years, Juanita.   The couple’s “mutual” and “amicable” split cost His Airness a cool $168 million clams—making it one of the most expensive celebrity divorces of all time. 

Thankfully for MJ, despite the divorce settlement and a history of gambling problems, in 2008 he still had enough of his Hanes Underwear fortune in tact to attract Yvette Prieto, a gorgeous Cuban model approximately half his age.  Despite years of engagement rumors, the two have been living together in unwedded bliss for years. 

My advice to Yvette—lock it down girl, you don’t want to be the baseball career in the life of a basketball legend. 

Tiki Barber: Ginny Barber for Traci Johnson

Tiki Barber, who is as evil as he is handsome, took the lowest possible road to acquire his upgrade, a road so low that even Tom Brady (probably) called it “messed up”—like the most seriously stone-cold low road on the map to Doucheville, which he happens to be mayor of. 

The former New York Giants running back and failed broadcaster married his college sweetheart, Ginny Cha, in 1999.  Their 10-year marriage, which ultimately produced four children, abruptly ended in 2010 when Barber left his eight-month-pregnant wife for a 23-year-old Tiki Barber fan and NBC intern.

Barber has had image problems for years, and it looks like his image might have finally been irreparably damaged.  During his NFL career, he was disliked by fans and teammates alike, ultimately retiring to pursue a short-lived career in broadcasting. 

Most recently, he demonstrated a total lack of self-awareness by describing the time he spent hiding out at his agent’s house with his new girlfriend after his split as “a reverse Anne Frank thing”—you know, because his agent is Jewish.

If there’s a silver lining here, it’s that the divorce settlement was so costly that he’s contemplating un-retirement—where surely he’ll get the welcome he deserves from fans (hint: it involves throwing soiled diapers). 

Pete Rose: Carol Rose for Kiana Kim

If you Google “Pete Rose divorce” you’ll notice that most headlines say something along the lines of “Disgraced Baseball Legend files for divorce”—which means that if a movie based on his life was made, the only thing shocking about this divorce would be that it came after an impressive 27 years of marriage. 

So overall, it was a net victory for a man whose name is synonymous for disgrace!

Naturally, Charlie Hustle, age 69, who filed for divorce in 2011, has been dating Playboy model Kiana Kim since 2009.  In 2010, Kim joined Rose on the Howard Stern show where he proceeded to brag about their sex life and she, I’m guessing, quietly contemplated the series of bad life decisions that ended with her naked in the bed of a 69-year-old disgraced baseball legend. 

My advice to Pete—lock it down dude and don’t forget the prenup because this girl is bound to Google you at some point, and then, you’ll never see her again if she’s not legally required to be there.

Tom Brady: Bridget Moynahan for Giselle Bundchen

In December 2006, New England Patriots quarterback Tom Brady had it all—a Hall of Fame career on the NFL team of the decade, movie star good looks, massive piles of money and a beautiful girlfriend in actress Bridget Moynahan, who was pregnant with the couple’s first child. 

In January 2007, New England Patriots quarterback Tom Brady had it all—a Hall of Fame career on the NFL team of the decade, movie star good looks, massive piles of money and a beautiful new girlfriend in supermodel, Giselle Bundchen—his future wife and future mother of his first legitimate child who possesses twice as many piles of money.  

And his image didn't even take a hit! It’s good to be king, ain’t it Brady?