NBA Buyer's Remorse: The 25 Worst Contracts in League History

Ben TeitelbaumCorrespondent IIOctober 21, 2010

NBA Buyer's Remorse: The 25 Worst Contracts in League History

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    NEW YORK - DECEMBER 06:  Gilbert Arenas #0 of the Washington Wizards drives past Stephon Marbury #3 of the New York Knicks on December 06, 2006 at Madison Square Garden in New York City. NOTE TO USER: User expressly acknowledges and agrees that, by downlo
    Chris McGrath/Getty Images

    "Show me the money!"

    Fictional wide receiver Rod Tidwell bluntly stated the importance of obtaining fat contracts. While some athletes consider money just a piece of the puzzle, others prioritize it as their primary motivation.

    Sports history is littered with teams throwing cash at players in hopes of winning championships. Certain franchises have consistently been able to buy success (NY Yankees), whereas others have been left with trophy cases as empty as their wallets (NY Knicks).

    As the major sports industry has flourished, player contracts have grown exponentially larger and now regularly exceed $100 million, especially in the NBA. Though you would think owners would only be willing to spend that type of money on surefire superstars, they have repeatedly taken risks on questionable guys that haven't panned out. In fact, it's often a crapshoot whether signees end up being worth the investment.

    Kobe Bryant has probably merited every penny the Lakers paid in giving him a 7 year $136 million contract in 2004. On the other hand, there are countless examples of players who didn't deserve deals anywhere near what they got.

    Here, those overpaid, undeserving bandits will be exposed.

    They've made a whopping $1.95 BILLION dollars and a meager 9 All-Star games combined. With that money, you could buy over 8,000 Lamborghini Gallardos, send over 12,000 kids through Harvard, enjoy Lakers courtside seats for over 20,000 seasons, and collect over 15 million pairs of Nike Hyperdunks.

    Professional snooker player James Wattana might have said it best: "I don't want to be a superstar. I just want to make superstar money." Well these 25 ballers got it right.

    I formally present the worst contract signings in NBA history.

25. Rashard Lewis: 6 Years, $118 Million

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    BOSTON - MAY 28:  Rashard Lewis #9 of the Orlando Magic warms ups against the Boston Celtics in Game Six of the Eastern Conference Finals during the 2010 NBA Playoffs at TD Garden on May 28, 2010 in Boston, Massachusetts.  NOTE TO USER: User expressly ack
    Jim Rogash/Getty Images

    Guess who is the second highest paid player in the NBA this season?

    Oh no, I think I gave it away. That's right, Rashard Lewis, at over $20 million.

    Unlike most of the players on this list, the Orlando Magic forward has been a dependably productive player each year of his contract (so far). His career hasn't come crashing to the ground, and he hasn't missed games due to injury, weight issues, felony charges, insurrections or substance abuse.

    In fact, Lewis was a 2009 All-Star. He has been a crucial starter on a team that made the NBA Finals in 2009.

    However, in no way is he worth the gigantic contract Orlando bestowed on him in 2007.

    $118 million should be reserved for MVPs, team leaders that carry their squads to the Finals, not for borderline All-Stars who need to rebound and defend better or shooters who can't hit big shots.

    While Lewis hasn't been a bust, he's making so much more money than he deserves. The final verdict isn't in yet, as Rashard is only halfway through his deal. Still, I can't see him justifying the investment.

24. Juwan Howard: 7 Years, $105 Million

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    18 Apr 1997:  Juwan Howard #5 of the Washington Bullets questions a call during their 104-93 win over the Orlando Magic at the USAir Arena in Landover, Maryland.  Mandatory Credit: Doug Pensinger  /Allsport
    Doug Pensinger/Getty Images

    Here's a fun fact for your local pub quiz night: Juwan Howard was the NBA's first $100 million man.

    A former member of Michigan's Fab Five, Howard was expected to pair with college teammate Chris Webber and spark a Washington Bullets renaissance in the mid 90s.

    Early on Howard impressed. In 1995-96 he was an All-Star and an All-NBA Third Team performer, averaging 22.1 points, 8.1 rebounds and 4.4 assists and leading the Bullets to the brink of the playoffs.

    All signs pointed towards Howard becoming a superstar, so the Bullets decided to lock him up for the long term.

    Make no mistake, Howard was a very good player for a while, putting up more than 17 ppg eight times. However, he never became the superstar he was supposed to be.

    While we can't blame the Bullets too much for the enormous contract, it still ranks as one of the worst of all time.

23. Brian Grant: 7 Years, $86 Million

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    LOS ANGELES - MARCH 27:  Brian Grant #55 of the Los Angeles reacts to a call during the game against the Philadelphia 76ers at the Staples Center on March 27, 2005 in Los Angeles, California. The Sixers defeated the Lakers 96-89.  NOTE TO USER: User expre
    Harry How/Getty Images

    Brian Grant was a solid NBA big man for a decade, a guy who always played hard, defended, and rebounded. Plus, he had some of the best dreads in NBA history.

    Perfect for a team's 7th man. Awful for $86 million.

    Grant was drafted 8th overall out of Xavier in 1994 and made First Team All-Rookie, so he was thought to have terrific potential.

    Problem was, that potential never quite panned out.

    In the summer of 2000, after several uninspiring years with the Kings and Blazers, Miami GM Pat Riley had the brilliant idea to offer him a max deal. In his first season he wasn't phenomenal, but he didn't disappoint. Grant averaged 15.2 points and 8.7 rebounds.

    Unfortunately he would only average double digits one more season in his NBA career.

    In a twist of good fortune for the Heat, though, Grant's massive contract helped make the blockbuster trade for Shaq work financially. So I guess in a weird way Grant was a key player in Miami's run to a championship.

    Otherwise, he might be sitting closer to the top of this list.

22. Jayson Williams: 6 Years, $86 Million

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    24 Mar 1999: Jayson Williams #55 of the New Jersey Nets stands under the basket as he waits during a game against the Detroit Pistons at the Continental Airlines Arena in East Rutherford, New Jersey. The Pistons defeated the Nets 84-71.
    Ezra Shaw/Getty Images

    The sad story that is Jayson Williams began well before the horrific night in 2002 when he accidentally shot and killed his limousine driver.

    He was a decent center throughout the 1990s and posted double-double averages in 96-97 and 97-98, though he was prone to injury.

    In the summer of 1998 the New Jersey Nets signed Williams to this enormous extension with high hopes that his play would continue to improve, meanwhile ignoring his injury-plagued history.

    Alas, repeated lower body injuries forced him to retire after playing just one up-and-down season.

    The only mitigating factor for New Jersey was that an insurance company paid for the rest of Williams' contract, so it didn't financially impact the Nets too much.

    Yet it remains a bonehead deal that shouldn't be forgiven.

21. Jon Koncak: 6 Years, $13.1 Million

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    Magic #45; getting owned by Luc Longley.
    Magic #45; getting owned by Luc Longley.Jonathan Daniel/Getty Images

    NBA franchises seem to be constantly searching for the elusive great white whale that is the dominant center. There have only been a handful in basketball history, and their teams have been unequivocally successful.

    Accordingly, teams gamble on unproven big men more than anybody else, and that is why they are often the most overpaid players and biggest busts.

    Enter Jon Koncak, the so-called father of the atrocious contract.

    Koncak had been nothing more than a middling backup center for the Hawks when Atlanta and Detroit commenced a 1989 offseason bidding war for his services. Why either team actually cared about signing him, no one knows.

    In order to prevent Koncak from joining their Eastern Conference rivals, the Hawks proffered this deal, which is minuscule by today's standards but was remarkably hefty at the time.

    Jon "Contract" was suddenly making more money than Michael Jordan, Magic Johnson, and Larry Bird.

    Although he managed to stay on the court consistently, it was mostly in a reserve role, and Koncak's best season was 4.1 points and 4.9 rebounds per game.

20. Erick Dampier: 7 Years, $73 Million

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    SAN ANTONIO - APRIL 25:  Erick Dampier #25 of the Dallas Mavericks in Game Four of the Western Conference Quarterfinals during the 2010 NBA Playoffs at AT&T Center on April 25, 2010 in San Antonio, Texas. NOTE TO USER: User expressly acknowledges and agre
    Ronald Martinez/Getty Images

    Speaking of risky contracts given to questionable centers, Erick Dampier fits the profile perfectly.

    Dampier is a classic case of the player whose production booms during a contract year. He was a paltry 8 point 6 board guy through his first seven years, most with the Golden State Warriors, but then his impending contract negotiations gave him enough motivation to turn up the effort and average 12/12.

    That "explosion" was enough to score him $73 million from the Mavs in the summer of 2004.

    Damp has started ever since, but he hasn't averaged double digits in points or rebounds once.

    The one thing he does consistently is foul. In fact, his foul rate is the only stat he has maintained with Dallas, so at least opposing post players aren't getting easy buckets.

    Overall, Dampier has been a big disappointment. However, he has not been as inadequate as the center he replaced...

19. Raef LaFrentz: 7 Years, $70 Million

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    LOS ANGELES - OCTOBER 25:  Raef LaFrentz #9 of the Portland Trail Blazers looks on during a preseason game against the Los Angeles Clippers at Staples Center on October 25, 2006 in Los Angeles, California.  The Clippers won 97-89.  NOTE TO USER: User expr
    Stephen Dunn/Getty Images

    Here's another Mark Cuban big man failure.

    Coming out of Kansas in 1998, highly touted center Raef LaFrentz was drafted 3rd overall by the Denver Nuggets.

    In his first four years in the league, he proved to be exceedingly mediocre, never surpassing 14 points or 8 rebounds per game, and halfway through the 2001-02 season he was traded to the Dallas Mavericks.

    The Mavs must have seen something the rest of the basketball world missed when they re-signed LaFrentz that summer to a $70 million extension. Wait, maybe Cuban was hallucinating when he thought up that idea.

    LaFrentz remained exceedingly mediocre throughout the rest of his career, not once demonstrating why he was given all that cash.

18. Tom Gugliotta: 6 Years, $58.5 Million

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    26 Feb 1999:  Tom Gugliotta #24 of the Phoenix Suns shoots a free throw against the Golden State Warriors at the Oakland Coliseum in Oakland, California. The Warriors defeated the Suns 94-90.   Mandatory Credit: Jed Jacobsohn  /Allsport
    Jed Jacobsohn/Getty Images

    In his prime, Tom Gugliotta was a well-rounded power forward who could do it all. In 1996-97 he put up 20.6 points, 8.7 rebounds, 4.1 assists, 1.6 steals and 1.1 blocks, pretty outstanding numbers.

    Too bad the Suns signed him past his prime.

    Before the lockout-shortened 98-99 season, Phoenix gave the 29-year-old "Googs" $58.5 million over 6 years, even though he was coming off an injury that caused him to miss the second half of the previous year.

    Sadly, the injury bug kept biting. Gugliotta appeared in barely more than half his games with the Suns, and after a solid first season his production plummeted.

    By the time Phoenix traded his $10 million per year away in 2004, he was seeing just 10 minutes per game.

17. Andrei Kirilenko: 6 Years, $86 Million.

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    EAST RUTHERFORD, NJ - DECEMBER 16:  Andrei Kirilenko #47  of The Utah Jazz in action against the New Jersey Nets during their game on December 16th, 2009 at The Izod Center in East Rutherford, New Jersey.  NOTE TO USER: User expressly acknowledges and agr
    Al Bello/Getty Images

    Three years into Andrei Kirilenko's NBA career, basketball enthusiasts everywhere were smitten with his ability and potential. As a do-it-all 22-year-old, he had "future superstar" written all over him.

    Like everyone else the Utah Jazz predicted AK-47 would become dominant on both ends of the court. Therefore, they gave him this colossal extension in the summer of 2004.

    Kirilenko hasn't been bad, but he has never lived up to the hype. The year before he signed his new deal remains his best season yet, and I doubt he will ever recapture the glory.

    Injuries, friction with coach Jerry Sloan, a suspect outside jumper and his professed desire to return to Russia have all caused his minutes and productivity to abate. The one time NBA blocks leader, a remarkable feat for a small forward, has seen his rejection average fall by over two per game.

    Over the past couple years Kirilenko has been relegated to mainly substitute duty, despite the fact that Utah pays him a top 10 salary.

16. Jim McIlvaine: 7 Years, 33.6 Million

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    11 Nov 1996:  Jim McIlvaine of the Seattle Supersonics runs up the court during their 110-94 victory over the Sacramento Kings at Arco Arena in Sacramento, California. Mandatory Credit: Otto Greule/Allsport
    Otto Greule Jr/Getty Images

    Oh, the story of Jim McIlvaine.

    It's not the size of the contract that puts him on this list; it's the fallout that the contract precipitated.

    In the summer of 1996, the Seattle Supersonics were coming off an NBA Finals appearance in which they lost the otherworldly Chicago Bulls.

    Rising superstar Shawn Kemp wanted an extension that, quite frankly, he deserved. However, Sonics management believed that an upgrade at center was a bigger priority.

    The choice of McIlvaine, though, is completely baffling. When signed, he was merely a former second round draft pick who had spent two wholly ineffective years in the league.

    In Seattle he never averaged more than 18 minutes or 4 points per game. He was traded to the Nets in 1998 and his contract was bought out in 2001.

    Let's now look at the greater consequences of his signing, the real damage.

    Never receiving that extension, Kemp felt betrayed by the franchise and became disgruntled. He forced a trade out of Seattle, and in return the Sonics received the inimitable Vin Baker.

    The Sonics never recovered, only making the playoffs four times in the next 11 years, and then moved to Oklahoma City.

15. Bryant Reeves: 6 Years, 61.8 Million

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    2 Nov 2000:  Bryant Reeves #50 of the Vancouver Grizzlies looks on during the game against the Los Angeles Clippers at the Staples Center in Los Angeles, California. The Grizzlies defeated the Clippers 99-91.  NOTE TO USER: It is expressly understood that
    Stephen Dunn/Getty Images

    And then there's Bryant "Big Country" Reeves, another center who may have caused the relocation of a franchise.

    A mammoth of a man, the Vancouver Grizzlies rewarded him in 1997 with a contract nearly as large as his body, even though his first few years in the league were rather pedestrian.

    How did he pay the Grizzlies back? Four decent years and then premature retirement due to a degenerative back condition. On the bright side, he did manage to lead the league once in field goal percentage and once in personal fouls.

    Reeves wasn't the bum history has made him out to be, but he may have indirectly driven the team out of Vancouver. His contract left the Grizzlies strapped for cash, which in turn left them predominantly winless, prompting the sale of the franchise and its subsequent move to Memphis.

14. Jermaine O'Neal: 7 Years, $126.6 Million.

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    NEW ORLEANS - DECEMBER 30:  Jermaine O'Neal #7 of the Miami Heat looks on during the game against the New Orleans Hornets at New Orleans Arena on December 30, 2009 in New Orleans, Louisiana.  NOTE TO USER: User expressly acknowledges and agrees that, by d
    Chris Graythen/Getty Images

    Center Jermaine O'Neal is an example of a prep-to-pro whose career has been quite the roller coaster, and he comes in at number 11 on this list because of the sheer size of his contract.

    He couldn't get off the bench during his first four years in Portland, as both his game and attitude lacked maturity, but then he exploded onto the scene with Indiana precisely a decade ago.

    After back-to-back 19 point, 10 rebound seasons in 01-02 and 02-03, O'Neal looked primed to be the Pacers' stalwart in the middle for a long while.

    Ergo, in the summer of 2003 he was offered the sun, moon, and stars.

    Through his first four seasons O'Neal lived up to expectations. He averaged roughly 20 points, 10 rebounds and 2.5 blocks per game, was selected an All-Star each year, and led his team to the playoffs three times and conference finals once. (Indiana lost to future champion Detroit in six games.)

    O'Neal's only disappointing quality was his durability. His first season under contract was the lone one he played in full. He missed 122 games between 2004 and 2008, and his production dropped dramatically. He became merely a decent player instead of a guy who could carry his team.

    Hindsight is 20-20, and at the time Indiana seemed justified in giving O'Neal that extension. As it worked out, though, O'Neal hasn't really earned his pay. As I mentioned with Rashard Lewis, for this type of epic money - almost $130 million!!! - you better be an MVP, win a championship, or at least be an All-NBA performer consistently.

    O'Neal just didn't get that done.

13. Eddy Curry: 6 Years, $56 Million

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    BOSTON - NOVEMBER 24:  Eddy Curry #34 of the New York Knicks looks on during a game against the Boston Celtics at the TD Banknorth Garden on November 24, 2006 in Boston, Massachusetts.  The New York Knicks defeated the Boston Celtics 101-77. NOTE TO USER:
    Elsa/Getty Images

    Eddy "Eat More" Curry is large and his weight issues are in charge.

    No one has ever denied Curry's ability to score the basketball. They've just denied his ability to rebound, defend, block shots, hustle, give effort, play hard, pass the ball and pass up the buffet.

    Another thing Curry couldn't pass up was the all-you-can-eat sized contract the Knicks conferred upon him in 2005.

    In New York he has had one legitimately good season, posting 19.5 points and 7 rebounds in 2006-07, sandwiched between two passable years.

    But recently Curry has been a train wreck. Health, weight and personal problems have limited him to 10 total games in the past two years.

    Who knows if he'll ever play valuable minutes again.

12. Jerome James: 5 Years, $30 Million

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    BOSTON - NOVEMBER 24:  Eddy Curry #13 of the New York Knicks looks on during a game against the Boston Celtics at the TD Banknorth Garden on November 24, 2006 in Boston, Massachusetts.  The New York Knicks defeated the Boston Celtics 101-77. NOTE TO USER:
    Elsa/Getty Images

    While $30 million is paltry compared to some of the other contracts on this list, center Jerome James' unmatched ineptitude easily places him this high.

    In the summer of 2005, the Knicks decided to take a gamble on James, who was coming off a decently successful playoff run with the Seattle Supersonics in which he tripled his season stats. Unfortunately for New York, those 11 playoff games were the only stretch of consistently good basketball James played in his entire career.

    Why did they expect great things? I don't really know. Those "big" playoff series only saw James average 12.5 points and 6.8 rebounds, not exactly stellar numbers.

    James was a complete bust with the Knicks. He was perennially out of shape and never averaged more than 3.1 points per game. He also battled injuries, playing in 4 total games in 2007-08 and 08-09.

    In fact, during those two seasons James played just 15 minutes, meaning he took home roughly $787,000 per minute. Compare that to Kobe, who made a comparatively pitiful $8,750 per minute.

    I guess it's better than those players who got paid to not play at all.

11. Kenyon Martin: 7 Years, $92.5 Million

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    SALT LAKE CITY - APRIL 30:  Kenyon Martin #4 of the Denver Nuggets stands on the court during their game against the Utah Jazz in Game Six of the Western Conference Quarterfinals of the 2010 NBA Playoffs at EnergySolutions Arena on April 30, 2010 in Salt
    Ezra Shaw/Getty Images

    How could you ever give $92.5 million to a guy with lips tattooed on his neck?!

    The Denver Nuggets inked Kenyon Martin to this monster deal in 2004, hoping that he would live up to his potential. Nevermind his liability to injury: two fractured legs in back-to-back years, one as a senior at Cincinatti and one as a rookie with the New Jersey Nets. Nevermind his limited offensive skills. Nevermind his reputation for being a bad teammate.

    With Denver, K-Mart has proved all the unfavorable opinions true. He has had two microfracture knee surgeries and was notoriously suspended during the 2006 playoffs for "conduct detrimental to the team."

    He's been pretty good on the court itself, but he has not come close to approaching All-Star level. While Martin has served as a solid role player on successful teams, he is definitely not a max deal player.

10. Peja Stojakovic: 5 Years, $64 Million

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    NEW ORLEANS - MARCH 08:  Peja Stojakovic #16 of the New Orleans Hornets reacts to a call against the Golden State Warriors at New Orleans Arena on March 8, 2010 in New Orleans, Louisiana.  NOTE TO USER: User expressly acknowledges and agrees that, by down
    Chris Graythen/Getty Images

    Oh Peja Stojakovic, a man once considered the best shooter in the NBA.

    He was an absolute stud for those great Sacramento Kings teams that challenged the Lakers' dominance of the early 2000s, averaging better than 18 ppg for six straight years while shooting over 40% from long range.

    In the summer of 2006, following a season in which Sac-town traded him to Indiana at the deadline, Stojakovic became a 28-year-old free agent ostensibly entering his prime.

    New Orleans/OKC at the time subsequently gobbled him up for a price that was substantial but not necessarily preposterous. Uniting a deadly shooter with dynamic young point guard Chris Paul and efficient big man David West could make their offense quite formidable, the Hornets figured.

    Regrettably, Stojakovic got old, fast. He missed most of his first season with back surgery and hasn't done much since. Though he has managed to score in double digits every year, his shooting percentages and effectiveness have dropped.

    When discussing the Hornets these days, everyone mentions their need for a perimeter scorer. "Mr. Stojakovic on line 1."

9. Allan Houston: 6 Years, $100 Million

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    NEW YORK - DECEMBER 26:  Allan Houston #20 of the New York Knicks holds the ball during the game against the Charlotte Bobcats on December 26, 2004 at Madison Square Garden in New York City, New York. The Knicks won 91-82.  NOTE TO USER: User expressly ac
    Jim McIsaac/Getty Images

    Allan Houston had some fantastic moments with the New York Knicks, including a buzzer beater against the Miami Heat in decisive Game 5 of the first round of the 1999 playoffs that sent the Knicks on their way to the NBA Finals.

    New York's decision to give Houston a maximum contract extension in 2001 was not necessarily a bad one, as he averaged over 20 points per game during his first two seasons.

    Regrettably, though, Houston started battling recurring knee injuries that restricted him to 50 games in 03-04 and just 20 games in 04-05. Following that season, he was forced to retire.

    Houston remained the league's second highest paid player for two full years after he competed in his last game, stockpiling vast sums of money on a couch somewhere.

    Houston's ill-fated deal was the first domino to fall in the Knicks' demise.

    To rub it in, the NBA's most recent Collective Bargaining Agreement instituted an amnesty clause - nicknamed the "Allan Houston Rule" - whereby teams could choose to waive one player whose contract would not count against the luxury tax.

8. Larry Hughes: 5 Years, $70 Million

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    NEW YORK - NOVEMBER 29:  Larry Hughes #0 of the New York Knicks looks to pass  against the Orlando Magic at Madison Square Garden November 29, 2009 in New York City. NOTE TO USER: User expressly acknowledges and agrees that, by downloading and/or using th
    Chris McGrath/Getty Images

    Time to be blunt: GMs need to stop trusting contract year performances.

    You see the phenomenon everywhere in sports (and I briefly touched on it earlier with Erick Dampier). Players try harder during the season right before their current deals expire, and consequently their statistics and apparent value spike.

    Front office personnel are repeatedly duped into believing these improvements are caused by players maturing or working hard in the offseason or figuring out the league or getting hyperbaric chambers or cutting out all sugars.

    I mean, there's the rare case in which one of these reasons is legitimate, but the "experts" offering the major dollars should be a bit more discerning.

    2004-05 was such a year for Larry Hughes, who put up awesome numbers with the Wizards (22 points, 6.3 rebounds, 4.7 assists, 2.9 steals).

    In the offseason the Cavaliers rewarded him with this mega deal, anticipating the Hughes/LeBron tandem wreaking havoc upon foes.

    Instead they got a guy who couldn't shoot and didn't care all that much about the other aspects of the game. Hughes shot less than 41% in Cleveland and showed little commitment to board or pass.

    Hughes was the first failed perimeter partnership in Cleveland, beginning a recurring trend that ultimately led to "The Decision." He was traded away less than three years into his contract.

7. Grant Hill: 7 Years, $93 Million

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    CHICAGO - APRIL 15:  Grant Hill of the Orlando Magic watches his team take on the Chicago Bulls from the bench on April 15, 2005 at the United Center in Chicago, Illinois. The Bulls defeated the Magic 117-77.  NOTE TO USER: User expressly acknowledges and
    Jonathan Daniel/Getty Images

    I feel awful for Grant Hill.

    In the late 90s, he was a true rising superstar with superb skills and even better character. 

    Hill was an All-Star his first six years in the league - I'm including the lockout-shortened season because he would have been - the 1994-95 Rookie of the Year and a 5-time All-NBA performer. His numbers were incredible; I recommend looking them up because they'll blow your mind. (Just to whet your appetite, did you know there was a year in which he averaged 20.2 points, 9.8 boards and 6.9 assists? I know...)

    Thusly, Hill was completely deserving of the humongous free agent contract he signed with Orlando in 2000.

    Unfortunately for both Hill and the Magic, the basketball gods had some unknown score to settle. They promptly struck Hill down with an serious and complicated ankle injury that took the better part of five years to heal.

    Hill played in only 41 percent of his team's games, effective but not transcendent when he was on the court. He was selected for one last All-Star team in 2005. In 2007, Orlando made their only playoff appearance with Hill on the squad, and they were swept by the Pistons.

    It is such a shame that the prime of Grant Hill's career was spent mostly in the doctor's office. Though he will forever be remembered for what never was, at least he has recently rejuvenated himself in Phoenix. It is with the utmost respect that I place him so high on this list.

6. Penny Hardaway: 7 Years, $86 Million

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    LOS ANGELES - DECEMBER 21:  Anfernee Hardaway #1 of the Phoenix Suns rests during the game against the Los Angeles Lakers at Staples Center on December 21, 2003 in Los Angeles, California.  The Lakers won 107-101.  (Photo by Stephen Dunn/Getty Images)
    Stephen Dunn/Getty Images

    Like Grant Hill, Anfernee "Penny" Hardaway was another ultratalented heir apparent to Michael Jordan.

    A big guard with a diverse skill set and hilarious ad campaign - who didn't love 'Lil Penny - he teamed with Shaq to take Orlando to the 1995 NBA Finals. He was a four-time All-Star and was chosen First Team All-NBA twice.

    Sad to say, the similarities to Hill don't end there. Hardaway blew out his knee in the fall of 1997, an injury that would haunt him for the rest of his career.

    Despite the knee problems, Phoenix gave Penny a giant deal in 1999, hoping he would stay healthy and still be a star.

    However, the knee failed Hardaway in just his second season with the Suns, and he required microfracture surgery. He would never score more than 12 points per game again.

    Though he had some respectable playoff series in Phoenix, Hardaway became nothing more than a fringe starter.

    Unlike Grant Hill, Penny never got the chance to revive his career. He faded into NBA oblivion, lastly seen playing 16 games for the Heat in 2007-08.

5. Vin Baker: 7 Years, $86 Million

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    SACRAMENTO, CA - FEBRUARY 20:  Vin Baker #42 of the Boston Celtics looks on during the NBA game against the Sacramento Kings at Arco Arena on February 20, 2003 in Sacramento, California.  The Kings won 105-83.  NOTE TO USER: User expressly acknowledges an
    Jed Jacobsohn/Getty Images

    In the NBA, players' fates always seem to intertwine. The next two guys on our list are forever connected, as they were traded for each other and then both excessively overpaid.

    Vin Baker, out of tiny Hartford College, was a beast for the Milwaukee Bucks in the mid-90s. He could score in a variety of ways and he rebounded well.

    Despite his output, he was shipped to Seattle before the 1997-98 season as part of a blockbuster three-team trade that sent Shawn Kemp to Cleveland.

    He continued his success in his first year with the Sonics, going for 19/8, and though his production dropped in year two, the franchise decided to offer him an extension in the summer of 1999.

    Baker's initial season under contract would be the last good season in his career, as he battled alcoholism and concomitant weight issues. "Vin and Tonic" was in and out of the starting lineup, and after being traded to, suspended by, and then released from the Celtics, Baker all but disappeared.

4. Shawn Kemp: 7 Years, $107 Million

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    Shawn Kemp #4 of the Cleveland Cavaliers stands on the court during a game against the Washington Wizards at the MCI Center in Washington, D.C. The Cavaliers defeated the Wizards 111-103.
    Doug Pensinger/Getty Images

    You've already heard much of Shawn Kemp's story in the tales of Jim McIlvaine and Vin Baker, but here's some more background.

    Young Shawn Kemp was one of the most exciting and fearsome players to ever grace the hardwood. He dunked with incomparable force, and his quickness was amazing for a man so powerful.

    The "Reign Man" paired with Gary Payton to lead the great Sonics teams of the mid-90s, but various dealings soured the relationship between Kemp and Seattle, ultimately triggering the trade to Cleveland in 1997.

    Kemp immediately received a new contract, becoming the fifth member of the $100 million club, along with Juwan Howard, Kevin Garnett, Shaq and Alonzo Mourning. The Cavs hadn't made it out of the first round of the playoffs since 1993 and they thought Kemp could be their savior.

    Although Kemp did have three statistically good seasons with Cleveland, he only took the team to the playoffs once. It became clear that he wasn't cut out to be a leader, or worthy of all that cash.

    By 2000, Kemp had ballooned in size and the Cavs gave up on him as the answer. They unloaded him (and more importantly his salary) to Portland, and Kemp practically fell off the face of the earth (and into drug rehab).

3. Ben Wallace: 4 Years, $60 Million

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    CHICAGO - DECEMBER 27:  Ben Wallace #3 of the Chicago Bulls stands on the court during the NBA game against the Miami Heat on December 27, 2006 at the United Center in Chicago, Illinois. The Bulls defeated the Heat 109-103. NOTE TO USER: User expressly ac
    Jonathan Daniel/Getty Images

    This move by the Chicago Bulls in 2006 was so dumb. I've been trying to find ways to justify it but I can't. It's impossible to spin this positively. While some other guys on this list didn't live up to their contracts, Ben Wallace never deserved his.

    You should never give $15 million a year to a guy with a career 6.2 points per game average, no matter how good he is defensely. Not even if he were given special permission to goaltend. End of discussion.

    But if you want to keep discussing, I've got more to say. Since they losing Eddy Curry - yeah I'm praising Eddy Curry - Chicago has lacked one thing: a post scorer. Their offensive imbalance has prevented them from competing with the best teams in their conference. So what do they do? Sign a one-dimensional defensive presence.

    Should I keep going? How about mentioning the fact that the Bulls were 7th in defensive rating the year before signing their future away to Wallace.

    I wonder how that conversation went between General Manager John Paxson and Coach Scott Skiles.

    Paxson: "We need to get better, Scotty. Tyson Chandler, Mike Sweetney and Othella Harrington just aren't pulling their weight down low."

    Skiles: "I agree. We're defending well, but we're too perimeter oriented on offense."

    Paxson: "Ok. So we're looking for a scoring big man. Got it."

    Skiles: "Is there anyone on the market who fits that description?"

    Paxson: "I don't know for sure, but Ben Wallace is available. We could sign him for $15 million per year."

    Skiles: "Great, let's do it!"


2. Stephon Marbury: 4 Years, $76 Million

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    LOS ANGELES, CA - JUNE 07:  Stephon Marbury of the Boston Celtics attends Game Two of the 2009 NBA Finals between the Los Angeles Lakers and the Orlando Magic at Staples Center on June 7, 2009 in Los Angeles, California. NOTE TO USER: User expressly ackno
    Stephen Dunn/Getty Images

    Most of us are already familiar with the saga of Stephon Marbury, one of the only men I know who has a tattoo on his head.

    Starbury signed the ginormous extension with Phoenix in summer of 2003, but it wasn't set to kick in until 05-06. He was traded to Knicks in January of 2004, so while we can't blame them for offering the contract, we can condemn them for willingly acquiring it.

    Marbury evidently has problems with authority; he has participated in several of the biggest player-coach feuds in NBA history, with Larry Brown, Isiah Thomas, and Mike D'Antoni. For the majority of 08-09, he was asked to stay away from all team activities. Although the Knicks were forced to pay him, they were not going to play him.

    Of all the crazy situations that have occurred in the NBA, missing 117 games over two seasons essentially for insubordination might take the cake.

    Who knows? Perhaps Marbury intentionally got himself removed from the team, which would then be one of the most brilliant business maneuvers of all time. He was able to pursue his other commercial enterprises while collecting over $40 million. Wow.

    Now, there is only one more troubled guard left to complete this ignominious list. He is...

1. Gilbert Arenas: 6 Years, $111 Million

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    PHOENIX - DECEMBER 19:  Gilbert Arenas #0 of the Washington Wizards reacts during the NBA game against the Phoenix Suns at US Airways Center on December 19, 2009 in Phoenix, Arizona. The Suns defeated the Wizards 121-95. NOTE TO USER: User expressly ackno
    Christian Petersen/Getty Images

    Congrats Gil, you're contract has officially been deemed worse than all of those other terrible deals.

    Let me throw some stats at you starting in 2007-08, the year before Gilbert Arenas obtained his ungodly extension from the Washington Wizards.

    3 years, 47 total games, 3 knee operations, 1 felony conviction, 88 total Wizards victories.

    They say numbers don't lie.

    Agent Zero has become the diametrical opposite of the charismatic leader he was once known to be.

    Some more fitting descriptions might be liar, fraud, coward and egomaniac.

    This was supposed to be his redemption year, when he would prove he is really worth the Wizards' investment. Instead, Arenas was yet again beset by controversy before the preseason was two weeks old; he admittedly misled the Wizards to believe his knee was sore in order to give teammate Nick Young more playing time.

    It is now all but confirmed that "Hibachi" wants out of Washington. Arenas' albatross contract makes him incredibly difficult to trade, especially considering how wary other teams are of Gilbert's physical and mental health.

    If the Wizards do find a way to move him, there is no way they will get equal value. If they don't trade him, chances are he is more of a distraction than anything.

    It's now lose-lose with Arenas. Even though he is only two years into his contract and only 28 years old, I firmly believe this will hold up as the worst contract of all time (or at least until the next one).

Honorable Mention Players

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    Adonal Foyle
    Adonal FoyleRobert Laberge/Getty Images

    Keith Van Horn: 6 years $73 million. Nets 1999

    Howard Eisley: 7 years $41 Million. Knicks 2000

    Austin Croshere: 7 Years $50 Million. Pacers 2000

    Adonal Foyle: 6 years $42 Million. Warriors 2004

    Tyson Chandler: 6 years $64 million. Bulls 2005

    Theo Ratliff: 3 years $35 million. Blazers 2004

    Brian Cardinal: 6 years $37 million. Grizzlies 2004

    Bobby Simmons: 5 years $47 million. Bucks 2005

Honorable Mention: Coach Larry Brown

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    PHOENIX - JANUARY 26:  Head coach Larry Brown of the Charlotte Bobcats during the NBA game against the Phoenix Suns at US Airways Center on January 26, 2010 in Phoenix, Arizona.  The Bobcats defeated the Suns in overtime 114-109.  NOTE TO USER: User expre
    Christian Petersen/Getty Images

    Although this list was specifically designed for players, Larry Brown had to find his way into this article.

    In 2005, the New York Knicks gave him a 5 year, $50 million contract to bring the team back to respectability. In Brown's tenure, however, all they did was become more of a laughingstock.

    Brown's Knicks went 23-59, and after the season the franchise bought out his contract for $18.5 million.

    Epic fail!

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