10 Egregiously Bad Sports Contracts

By: Dave Roos
Sports Image Gallery Alex Rodriguez of the New York Yankees warms up before a Grapefruit League game against the Baltimore Orioles in March 2011. See more sports pictures.
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Professional athletes are worth every last penny they make. Yes, you heard us. Sure, pro athletes make millions and millions of dollars for playing a game, but the game pays back.

Let's take boxer Floyd Mayweather Jr., for instance. Mayweather made $65 million in 2010 just for punching another man in the face. On the surface, that's sounds absurd. But when you take into account that over 1.4 million people bought his fight against Shane Mosley on pay-per-view for a total of $78.3 million -- and that's just the one-time television revenue -- you start to see how sports math adds up [source: Rafael].


Another great example is Los Angeles Lakers guard Kobe Bryant, who made $48 million in 2010. Yes, Kobe is one of the NBA's reigning superstars, but should any man make 120 times more than the president of the United States for chucking a ball through a hoop? Absolutely not. But then you realize that Kobe's No. 24 jersey is the best-selling NBA jersey in the world (the world!) and retails at $45 a pop, with a large percentage of those sales going back the Lakers front office, and suddenly the ridiculous sounds a lot more reasonable [source: ESPN].

But then again, return on investment is a tricky thing. For a sports franchise to make stadium-loads of dough, they often have to throw large sums of cash at professionally unproven prospects. And in retrospect, what looks like a smart bet on a future superstar often turns out to be an egregiously bad business decision that sends the club spiraling into bankruptcy.

The following is our list of the 10 biggest contract catastrophes in professional sports, starting with Heisman Trophy-winning running back Ricky Williams.

10: Ricky Williams

Coming out of college, Ricky Williams was nothing short of a football god. During his four years at the University of Texas, the dreadlocked running back broke the all-time NCAA Division I rushing record (held by Tony Dorsett for 22 years), the all-time Division I rushing touchdown record -- and capped it off with the 1998 Heisman Trophy.

In 1997, legendary NFL coach Mike Ditka came out of retirement to revive the beleaguered New Orleans Saints. Despite the Saints' desperate need of a quality quarterback, Ditka decided to bet everything on Williams, trading all of their 1999 draft selections (plus first- and third-round choices in 2000) to the Washington Redskins in return for the chance to snap up the unproven college star [source: Baker].


In a strange move that would serve as an omen for the weirdness to come, Williams chose an inexperienced agent from rapper Master P's fledgling agency No Limit Sports. As a result, Williams' contract with the Saints was a mess. On the surface, it was a seven-year, $68 million deal. But thanks to a convoluted incentives structure, Ditka's next superstar only received the league minimum for his first two years and $5 million of his $8.84 million signing bonus was deferred [source: Baker].

The suffering Saints didn't get a whole lot out of the deal, either. Williams hurt his ankle in the first season, only scoring two rushing touchdowns. Things picked up in the next season, but by then his odd behavior -- conducting post-game interviews with his helmet on, rumors of heavy marijuana use, a teammate-bashing article in "ESPN: The Magazine" -- sealed his fate. After three unproductive seasons, Williams was traded to the Miami Dolphins, and Ditka -- who had once posed with Williams for a magazine cover as bride and groom (Ricky was the bride) -- retired for good [source: ESPN].

9: Ryan Leaf

Chargers quarterback Ryan Leaf prepares to throw a pass against the Pittsburgh Steelers in December 2000.
Stephen Dunn/Getty Images

Like Ricky Williams, Ryan Leaf was one of the top college prospects in the U.S. when the San Diego Chargers traded three draft picks and a four-time Pro Bowl player to the Arizona Cardinals for the right to grab the young quarterback in the 1998 draft [source: Spratt]. In a flash of fortuitous brilliance, the Indianapolis Colts passed on Leaf to draft another highly touted quarterback, Peyton Manning.

Leaf signed a four-year, $31.25 million contract with the Chargers, including a guaranteed $11.25 million signing bonus -- the largest ever paid to a rookie at the time. Blame it on the big-money pressure, but the poor quarterback's career was doomed from the start. A shoulder injury kept him sidelined for a whole season and when he was back in the game, he only managed a 4-17 record as a starter. An eventual trade to the Dallas Cowboys was the beginning of the end.


The former multimillion-dollar draft selection went on to work as an assistant golf coach at West Texas A&M before being convicted of eight felony counts of illegal prescription drug possession and getting canned [source: Johns]. In December 2010, Leaf received yet another contract, to write three books about winning, losing, addiction -- and what it feels like to be one of the biggest busts in NFL history [source: Spratt].

8: Allan Houston

No one can rightfully call Allan Houston's career a "bust." When he ultimately retired (for the second time) after nine seasons with the New York Knicks, he ranked among the top 10 scorers in franchise history. But unfortunately for Houston, he'll ultimately be remembered less for his on-court heroics -- his buzzer-beater in game 5 of the opening round of the 1999 playoffs was one of the most dramatic in Knicks history -- than for his 2001 contract extension for a ridiculous $100 million over six years.

Achilles had his heel and Houston had his knees. Chronic knee pain would haunt him for most of his post-giant-contract years with the Knicks, included two seasons where he played a grand total of 20 games, but still received his nearly $20 million annual salary [source: Associated Press]. The $100 million albatross on Houston's back made him virtually untradeable, draining millions from the Knicks' coffers and drawing vocal complaints of mismanagement from the team's diehard fans, who had watched the fabled franchise nosedive since the 2000 departure of Patrick Ewing.


In 2005, the NBA instated a new amnesty clause that would allow a team to release its top-paid player and avoid a one-time luxury tax payment on wages in excess of the salary cap [source: Stein]. Ironically, even though the new exemption came to be known as the "Allan Houston Rule," the Knicks inexplicably chose not to release Houston [source: Maxim]. After attempting a comeback in 2008, Houston retired after one pre-season appearance.

7: David Beckham

David Beckham of the Los Angeles Galaxy plays in an exhibition match in San Diego, Calif., in March 2011.
Kent Horner/Getty Images

David Beckham is the most famous soccer, er, football player in the world. At age 34, after brilliant careers with Manchester United and Real Madrid, during which he won all sorts of championships and cups and other prizes that make little to no sense to anyone this side of the Atlantic, he stunned the world by signing with the Los Angeles Galaxy of Major League Soccer. The shock was less over his decision to play football, er, soccer in a country that routinely abandons the sport after junior high than the outrageous size of his contract: $250 million over 5 years.

Now, let's be fair. The $250 million turned out to be more of a publicity stunt than a cash guarantee. Beckham's complex contract includes lots of provisions -- cuts of jersey sales, ticket sales and endorsements -- that depend on both his and the team's performance. When you do the math, Beckham is only guaranteed to earn about $50 million for the entire five-year contract [source: Wahl].


Beckham may be ruggedly good-looking, but the man is well past his prime as a footballer. Since joining the Galaxy, he's been plagued by ankle and knee injuries that limited him to just five games in 2007 and have hobbled his effectiveness ever since. In his four seasons in America, he has scored just nine goals and tallied 16 assists. Los Angeles would've been better off investing that $50 million in Posh's clothing line.

6: JaMarcus Russell

Taking a page from the Ryan Leaf playbook, JaMarcus Russell is another stellar college quarterback whose transition to pro ball was ... what's the opposite of stellar? Subterranean?

The Oakland Raiders snapped up the quarterback from Louisiana State University in 2007, fresh on the heels of Russell's MVP performance in the Sugar Bowl. But Russell's NFL debut was delayed while his agents hammered out one of the most lucrative (and eventually ludicrous) contracts in NFL history. Russell didn't attend a single day of training camp until he signed his six-year, $68 million deal. It turned out that Raiders coach Lane Kiffin was against the acquisition, but owner Al Davis pushed it through [source: Tafur].


The risk of this type of contract is that it's built entirely on expectation, not performance, and Russell would prove a monumental disappointment [source: Henderson]. Chronically overweight, Russell was in no shape to start for the Raiders until the very last game of the regular season [source: Pasquarelli].

Despite continuing problems with his weight -- he ballooned to 290 pounds (131.5 kilograms) during one off-season -- he held his starting position until his lackluster on-field performance earned him the third-string spot. An arrest for drug possession was the final straw and the Raiders released him in 2010. Over his three meager seasons with the Raiders, Russell was paid $39 million, which breaks down to $5 million per win and over $2 million per touchdown pass [source: Raber].

5: Steve Young

San Francisco quarterback Steve Young tries to avoid a Cowboys sack in the 1993 NFC Championship Game.
James Smith/Getty Images

Steve Young is one of the greatest NFL quarterbacks of all time. In his 1994 season with the San Francisco 49ers, he threw for 3,969 yards and 35 touchdowns, and was named MVP of the Super Bowl. But what few people know is that Steve Young was also one of the greatest quarterbacks ever to play in the USFL. Huh? What's that?!

You're forgiven if your memory's a little hazy. The United States Football League was a rival football league launched in 1983 that actually snatched some stars from the NFL before folding under massive financial failure in 1987. In 1984, Steve Young was an All-American out of Brigham Young University who was courted by several professional clubs, including the Los Angeles Express of the USFL. But it was only the Express who offered him a $40 million, 43-year contract. Yes, a 43-year contract.


All right, technically it's a four-year playing contract for $5.9 million with an additional $34.5 million in deferred payments. How do these deferred payments work, exactly? Young signed the contract when he was 22. Starting at age 28, he would receive annual payments beginning at $200,000 and increasing to $3.173 million for the final payment of his contract, sometime in the year 2027 [source: Kirshenbaum].

But the most egregiously absurd clause of the contract on the owners' side is that they guaranteed these payments even if the USFL went belly up (which it did) or Young decided to flee for the NFL after he wrapped up his four-year commitment to the Express. So somewhere, Steve Young is shining his three Super Bowl rings (he backed up quarterback Joe Montana for his other two) and collecting a fat annual check for the three forgettable (but not regrettable) years he spent in Los Angeles.

4: Alex Rodriguez

Alex Rodriguez, aka A-Rod, is synonymous with the New York Yankees' dominance in the late "aughts," including a World Series title in 2009. But before he played in pinstripes, he was a hotshot shortstop coming off some impressive All-Star seasons with the Seattle Mariners. The year was 2001 and the Texas Rangers were looking for a marquee player to lead them to the World Series, or at least the American League playoffs, a level of postseason play they hadn't reached in franchise history. They believed that savior was A-Rod.

Apparently, it's good to be the savior. Texas offered Rodriguez the highest paying contract in baseball history, a bank-busting $252 million over ten years. The contract, unfortunately, was cursed from the start. No matter how well A-Rod performed in Texas, he would never outlive the enormous folly of those $252 million. He belted in 52, 57 and 47 homeruns in the three years he played for Texas and always had a .300-plus batting average. Of course, it would come out later that he was using steroids during this period, but A-Rod cited the pressure of living up to his absurdly big paycheck.


Even with A-Rod's solid (albeit juiced-up) performance and the Rangers' all-in investment in him, none of it changed the team's fate. The Rangers never did made it to the playoffs (not until 2010, at least), and when the team recently filed for bankruptcy as part of a sale to ex-Rangers star Nolan Ryan, the largest creditor still on the books was one Alex Rodriguez, for $24.9 million [source: Morath].

3: Rick DiPietro

Islanders goalie Rick DiPietro in action against the Pittsburgh Penguins in February 2011.
Justin K. Aller/Getty Images

When we talk about professional sports with disgustingly high salaries, hockey is usually the exception. Maybe that's because we haven't been paying close enough attention: In 2006, for example, a young goalie named Rick DiPietro signed a 15-year contract -- the longest in NHL history at the time -- with the New York Islanders for $67.5 million. And those are American dollars, not the coins with a picture of a duck on them.

DiPietro had been with the Islanders franchise since 2000, when he was drafted out of Boston College at the ripe old age of 19. After a lackluster first season in the pros, the Islanders sent him back down to the minors for retooling. He came back strong in 2005, even earning a starting spot for the U.S. in the 2006 Olympics.


But just as DiPietro was hitting his stride, and just after he signed that whopper of a contract, his health went south. Unfortunately, goaltending -- like catching in baseball -- is notoriously tough on the knees. And despite DiPietro's youth, after a few quick seasons in the NHL, his knees have all the responsiveness of an arthritic septuagenarian's. As DiPietro rides the pine with an icepack on his lap due to knee swelling and a variety of other injuries, the Islanders continue to shell out $4.5 million a season. And thanks to the incredibly shortsighted long-term contract he signed, the team will continue to do so until 2021, even if DiPietro has to retire from his injuries [source: Raber]. And good luck trading him; his awesomely absurd contract will travel with him wherever he goes.

2. LeCharles Bentley

At 6 feet, 2 inches (1.88 meters) and 313 pounds (142 kilograms), there are very few things that can stop LeCharles Bentley. Ironically, the former Pro Bowler's career was derailed by one of the smallest creatures on Earth, a single-celled bacterium called staphylococcus aureus.

Bentley, a beefy offensive lineman, played four successful seasons with the New Orleans Saints before the Cleveland Browns picked him up as a free agent in 2006. Bentley's contract, beefy in its own right, was for $36 million over six years. The contract became so overpriced partly because the NFL had just agreed to add $7.5 million more to the free agent salary cap. The Browns entered the 2006 "free agency frenzy," as one ESPN.com columnist described it, with lots of money to spend, wisely or unwisely [source: Pasquarelli].


Unlucky is more like it. On the very first drill of the very first day of training camp, he tore a tendon in his knee that required immediate surgery. While recovering in the Browns' rehab facilities, Bentley contracted a vicious staph infection that he claims almost cost him his leg and even his life [source: Grossi]. Bentley and another teammate have sued the Browns for failure to maintain sanitary conditions in its training facilities.

Bentley's contract turned out to be a total loss for the Browns, who ended up paying the injured lineman $16 million in salary for a grand total of zero minutes of playing time [source: Neumann].

1: Kevin Brown

Los Angeles Dodgers pitcher Kevin Brown goes to work in a 2003 game against the Montreal Expos.
Lisa Blumenfeld/Getty Images

Kevin Brown was 33 years old in 1998; a free agent (for the third time) with 12 seasons of experience as one of professional baseball's most effective starting pitchers. As major league pitchers go, Brown was a bona fide veteran. His favored pitch, the sinkerball, was a modified fastball that's as arm-wrenching as any in the business. How many more seasons could he be expected play at this level before snapping a tendon or throwing out an elbow? Two, maybe three?

How about seven? That's the number the expert prognosticators at the Los Angeles Dodgers' headquarters came up with when drawing up a contract for the aging hurler. Seven years and a whopping, eye-popping, jaw-dropping $105 million, making Kevin "Old Man" Brown the first $100 million man in baseball.

Kevin Malone was the Dodgers' manager at the time, and even he doubts the sanity of the decision (funded by News Corp. cash) to extend a long-term contract to a guy nearing the end of his career.

"Did it make sense?" Malone told The New York Times in 2010. "No. Seven years for a pitcher is a lifetime. It's just scary, and any general manager who tells you it isn't, well, I'm not sure what calculations they are going by" [source: Brown].

Brown went on to pitch superbly for two whole seasons before tearing a muscle in his right elbow and injuring his neck in 2001. After that, he managed one more All-Star season for the Dodgers in 2003 before being traded to the New York Yankees and ending his career hobbled by injuries. In retrospect, the smarter money, and much less of it, would have gone to signing Brown for a three-year contract, but who could have predicted that a 33-year-old fastballer would get injured? Oh yeah, everybody.

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