50 of the Most Overpaid Players and Coaches in Recent Sports History

Amber Lee@@BlamberrSports Lists Lead WriterJanuary 16, 2012

50 of the Most Overpaid Players and Coaches in Recent Sports History

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    In reality, most athletes are overpaid, at least compared to us mortals, but that's just the world of professional sports. These guys provide a valuable service that the vast majority of the population could not, and they generate enough money to justify their bloated paychecks.

    Well, some of them justify their paychecks. Players like Alex Rodriguez and Michael Vick may be bringing home buckets of cash, but their play and star power combined ultimately makes them worth the money.

    In other words, they're overpaid relative to the average person, but they've still earned their money.

    Not all professional athletes are superstars, though. In fact, most aren't. The majority are role players, specialists or backups—many of whom inadvertently stumble into inexplicably massive contracts.

    The same goes for well-paid coaches too—most of them manage to win enough games to help the team contend and generate revenue, but there are always some who don't live up to expectations.

    In every league, it seems there's always someone willing to overpay for mediocrity. In the last several years alone, there have been countless examples of this phenomenon.

    Here are 50 of the most overpaid players and coaches in recent (North American) sports history that stick out to me most. If you feel I left anyone out, post in the comments section below.

50. Mike Vanderjagt, Dallas Cowboys

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    Leave it to the Dallas Cowboys to overpay for the original "idiot kicker." Seriously, this dude put the "Jag" in "Vanderjagt."

    When the Cowboys signed Mike Vanderjagt, the most accurate kicker in NFL history, in early 2006, they assumed their woes in the kicking game were behind them. But they were wrong.

    Over the first three months of the season, Vanderjagt's kicking percentage was just 72 percent—the lowest of his nine-year career. He was released before the end of the season, on November 27, 2006.

    The average salary of a kicker in the NFL is approximately $870,000; Vanderjagt was signed to a three-year deal worth $5.4 million. Despite being cut less than a season into his contract, Vanderjagt walked out of Dallas with almost $4 million.

49. Jake Peavy, Chicago White Sox

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    You can’t fault 2007 Cy Young winner Jake Peavy for a promising career marred by injuries. 

    But you also can’t ignore the fact that since being traded to the White Sox in 2009 as part of a three-year, $52 million deal, Peavy has averaged seven wins a season with a 3.57 ERA. 

    Earning a $16 million salary in 2011, he struck out 95 batters, equating to $168,421 per strikeout.

48. Ryan Howard, Philadelphia Phillies

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    Phillies slugger Ryan Howard isn’t a “bad player,” but he is (or will eventually be) one of the most overpaid players in sports history.

    After an impressive four seasons, the Phillies signed Howard to a five-year, $125 million contract extension in 2010, which keeps him in Philadelphia through 2016—one of the largest contracts in sports history.

    Howard’s production sharply declined in 2010 and 2011, but he still earned about $20 million in each season.

    In 2011, that production breaks down like this:

    Per Home Run: $606,060
    Per RBI: $172,413
    Per Hit: $141,843

47. Brad Miller, Bulls, Rockets and Timberwolves

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    Timberwolves center Brad Miller’s career peaked in 2004-05, but he’s managed to ink three lucrative deals since then, despite his steady (and substantial) decline.

    In 2009, Miller returned to the Bulls via a trade with the Kings. In 2009-10, he averaged 8.8 points per game, five rebounds and 24 minutes per game. It only cost the Bulls $12.3 million!

    Miller went on to sign a three-year, $15 million deal with the Rockets in 2010, but was traded to the Timberwolves, where he has yet to play a game due to injury, in 2011.

46. Joker Phillips, University of Kentucky

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    The University of Kentucky is never going to be mistaken for a college football powerhouse. But over his seven-year tenure, former head coach Rich Brooks improved the program’s talent and made the school a more respectable member of the SEC. 

    Brooks announced his intention to retire at the end of the 2009 season, naming wide receivers coach Joker Phillips as the head-coach-in-waiting. Phillips’ promotion earned him a contract paying $1.7 million per year and he’s returned the favor by leading the Wildcats to consecutive losing seasons.

45. Scott Gomez, Montreal Canadiens

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    Since a career-high 33 goals and 84 points for the Devils during the 2005-2006 season, center Scott Gomez has been an underwhelming player in the NHL. 

    But, that didn’t stop the New York Rangers from awarding him a seven-year, $51.5 million dollar contract in 2007, before they gladly traded the underachiever and his cap-hit to the Montreal Canadiens just one season after inking the deal. 

    Earning $7.1 million this season, Gomez makes $400,000 more than all-star Red Wings center Pavel Datsyuk, and in 15 games has five points, no goals, and is -2.

44. Carlos Pena, Chicago Cubs

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    No one disputes that 2008 Golden Glove winner, first basemen Carlos Pena is one of the best at the position. However, it is a legit question to ask what the career .239 batter brought to the Cubs when he was signed to a one-year, $10 million dollar deal in 2010. 

    On a team that was 10th in runs scored and ninth in slugging percentage in National League, Pena is far from a power hitter and finished the 2010-2011 season with a .225 batting average and 80 RBI’s. 

    And, not surprisingly, the Cubs watched the playoffs from home once again.

43. Chris Hope, Tennessee Titans

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    The Steelers have a knack for not overpaying players who enter free agency and Chris Hope is no exception.

    After winning Super Bowl XL with the Steelers, Chris Hope was signed by the Titans in 2006 to a six-year, $30 million dollar contract.

    In 2011, Hope made $6.5 million dollars as his base salary; the same as future Hall of Famer Ed Reed and almost double the base salary of former teammate and future Hall of Famer Troy Polamalu.

42. Brian Cardinal, Memphis Grizzlies & Minnesota Timberwolves

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    The Timberwolves are one of the worst franchises in the NBA because they trade for losers like Brian Cardinal, who are signed to a six-year deal worth $37 million.

    When the T-Wolves traded for him in 2008, Cardinal was a career backup who had played for five teams in nine years. Presumably they were aware of his previous season with the Grizzlies; Cardinal averaged 3.4 points, 2.6 rebounds and 12 minutes per game.

    His performance did not improve in Minnesota and he was traded to the Knicks, who waived him the same season. He briefly rejoined the T-Wovles before signing with the Mavericks in September 2010.

    Cardinal signed with the Mavs for the league minimum in December 2011, but he's still got more rings than LeBron. Zing!

41. Oliver Purnell, DePaul

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    Success in college hoops is defined by one factor: making, and going deep into, the NCAA Tournament.  Best record in the Atlantic-10? Meh. Win the Big East? Big deal. NIT champion? Puh-lease.

    Yet, second year DePaul head coach Oliver Purnell is making a cool $1.8 million despite never winning a tournament game in his 20+ year career. Adding insult to injury, DePaul went 7-24 in Purnell’s first season (that’s over $250k a win).

40. Aaron Rowand, San Francisco Giants

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    I’m not saying Giants center fielder Aaron Rowand didn’t deserve to get a huge contract for sacrificing his face to make a catch, but it doesn’t mean he wasn’t overpaid based on his production as a player. 

    After breaking multiple bones in his face making his famous catch, Rowand landed a five-year, $60 million dollar deal with San Francisco in 2007. 

    The career .273 hitter was decidedly lackluster with his new team and the Giants finally acknowledged their mistake in 2011, designating Rowand for assignment.

39. DeSagana Diop, Dallas Mavericks & Charlotte Bobcats

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    DeSagana Diop was drafted by the Cavaliers in 2001, where he had a largely unimpressive four years as a backup.

    He was then signed by the Mavericks in 2005, where he spent three underwhelming seasons as a serviceable defender, before being traded to the Nets in 2008.

    Diop was released by the Nets just months later, and the Mavs signed him to a six-year deal worth $32 million. In 2009, the Bobcats made the mistake of trading for Diop and his $5.3 million per year salary.

38. Matt Cassel, Kansas City

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    The NFL loves back-up quarterbacks. Kevin Kolb, Matt Flynn, Matt Moore…the list goes on and on. No position has made more money off less of a resume than the second-string quarterback.

    Enter, Matt Cassel. Tom Brady suffers a season-ending knee injury in the first game of the 2008 season, Cassel comes in and is okay. Then finds himself with a six-year, $63 million dollar deal as a Kansas City Chief.

    Cassel, who wasn’t a starter during his college career, had an up-and-down stint with the Chiefs before suffering a season-ending hand injury. Now, Kyle Orton is in town and Romeo Crennell is the new head coach.

37. Danica Patrick, IndyCar/Nascar Racing

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    In August 2011, Forbes magazine reported that race car driver Danica Patrick was the third-highest-paid female athlete in the world. Patrick’s earned income topped $12 million in 2011.

    That figure is the combined total of her income from races, personal endorsements and modeling. Patrick is absolutely entitled to her earnings, but consider her performance in 2010 compared to that of Nascar driver Kyle Busch in the same year.

    Patrick finished in 2nd place in two races, 6th place in another and finished 10th in the IndyCar championship points for the season. Busch finished the year with 24 race wins across Nascar’s three Series: Cup, Nationwide and Truck.

    Patrick earned just $1 million less than Busch the following year.

36. Gibril Wilson, Raiders

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    The Raiders never met a player they didn’t want to overpay. However, Gibril Wilson was so bad, so overpaid, that even the late Al Davis shipped this bum out after a single season.

    Benefiting from being on the Super Bowl winning Giants, Wilson leveraged his affiliation into a six-year, $39 million dollar deal with the Raiders. The third highest paid safety in 2008, Wilson was released by Raiders after the season, before being signed, and cut, by the Dolphins.

    Wilson was out of football in 2010, before being signed by the half-way house better known as the Cincinnati Bengals in 2011.

35. Ville Leino, Buffalo Sabres

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    In July 2011, the Sabres signed free agent Ville Leino to a six-year deal worth $27 million. In his first 20 games with the Sabres, their new center tallied just two goals and three assists.

    Leiono was unhappy with his switch in position, and by December was insisting he return to left wing.

    Wow! An overpaid, under-producing, whiner who is never short on excuses! Where do I sign??? ("I" in this case, is the Sabres)

34. Andrés Nocioni, Sacramento Kings

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    In 2010, Kings forward Andrés Nocioni raked in a cool $7.5 million. It was one of the highest earning and lowest producing seasons of his career. With the Kings in 2008-09, Nocioni averaged 13.7 points, six rebounds and 31 minutes of playing time per game.

    In 2009-10, his average points dropped to 8.5, rebounds to three, and playing time to 20 minutes per game. In 2010, Nocioni was traders to the 76ers, where his production has continued to decline.

33. Vernon Carey, Miami Dolphins

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    In 2011, offensive tackle Vernon Carey restructured his six-year, $42 million dollar contract signed with the Dolphins in 2009. 

    The reworking of his contract brought the numbers back down reality after cashing in on the OT gravy train. 

    Never a dominant player at his position, Carey just benefited from a grossly inflated market.

32. Juan Pierre, Chicago White Sox & Los Angeles Dodgers

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    Outfielder Juan Pierre landed a five-year, $44 million dollar contract with the Dodgers in 2007, where he hit exactly one home run in three seasons, before being shipped to the White Sox.

    In two seasons with the White Sox, Pierre padded his stats with three home runs and a .277 batting average. At least Chicago can take solace in the fact that the Dodgers were still on the hook for his salary.

31. Gilbert Arenas, Washington Wizards & Orlando Magic

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    If Gilbert Arenas wasn’t the type of person who brings a gun into the locker room to threaten teammates, he probably wouldn’t be considered terribly overpaid. But, unfortunately, Arenas is the type of player who brings a gun into the locker room to threaten teammates.

    Despite injuries and inconsistent play, the Wizards inked a six-year deal with Arenas worth $111 million in 2008. When Arenas’ off-the-court behavior got out of hand in 2009, the Wizards traded him to the Magic for the only player in the league more overpaid than Arenas.

    And that would be...

30. Rashard Lewis,Orlando Magic & Washington Wizards

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    At this point, it’s safe to say that everyone on the Wizards payroll is overpaid. In 2007, Rashard Lewis was signed to a six-year deal worth $118 million by the Magic, the biggest contract in franchise history.

    Lewis earned his paycheck for the next two seasons before testing positive for banned substances in 2009. His performance declined substantially after the test, and he was traded to the Wizards in 2010.

    Lewis pocketed $20.5 million his first year in Washington—far too much for anyone on a team that finished 23-59.

29. Marc Bulger, St. Louis Rams

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    In 2009, Rams quarterback Marc Bulger was the 24th ranked quarterback in the NFL. Over three years he threw for 27 touchdowns and 34 interceptions—yet Bulger collected an epic $31 million over that time.

    Bulger's salary over that period made him one of the highest paid players in the NFL.

28. Alfonso Soriano, Chicago Cubs

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    You have to hand it to the Chicago Cubs—they have found the right formula for spending a whole lot of money without getting any better. There are cheaper ways to finish in the basement of that division, right Pirates?

    Case in point: Signing left fielder Alfonso Siriano to an eight-year, $136 million dollar mega-deal in 2006—the biggest in franchise history and fifth largest in MLB history. In five seasons with the Cubs, Soriano has batted .264 and averaged 26 home runs per year. 

    Thanks to a no trade clause, the Cubs are hoping Soriano is especially generous and another team is especially dumb.

27. Tim Connolly, Toronto Maple Leafs

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    If you’re a hockey fan, you can’t help but feel that the decades of mediocrity plaguing the once great Maple Leafs franchise is bad for the NHL. It's bad for the sport in general.

    The 2010 signing of free agent center Tim Connolly is indicative of the team’s struggles to assemble a consistent winner. After a few solid seasons with the Sabres, Connolly inked a two-year, $9.5 million dollar deal with Toronto. Very rich for the NHL.

    So far, Connolly has struggled to stay on the ice due to injuries and in 32 games has just seven goals and 22 points. He's on pace to score 17 goals at $279,411 each.

26. Al Harrington, New York Knicks

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    Al Harrington was signed by the Isiah Thomas era Knicks in 2008. At the time Harrington was scoring 14 points per game in his career, but converting only 40 percent of his shots.

    In 2010, Harrington’s production was down across the board, but the Knicks paid him $10 million. Well not everything was down--his turnovers were up!

    The Knicks finally wised up and let him walk after that season and the Nuggets signed him to a deal that paid him $5.7 million in his first year with the team.

25. Derek Dooley, Tennessee

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    After getting royally screwed by Lane Kiffin, you can’t blame Tennessee for going a completely different direction with their next head coach.

    The son of legendary Georgia coach and athletic director Vince Dooley, Derek Dooley has SEC football ingrained in his DNA. Ignoring the fact he was a lackluster 17-20 in three seasons as Louisiana Tech’s head coach, Tennessee hired Dooley, paying him over $2.1 million per year. 

    In his first two seasons at UT, Dooley has gone 11-14, and the once elite program now celebrates wildly when it beats…Vanderbilt.

24. Vernon Wells, Los Angeles Angels of Anaheim

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    That popping sound you heard on Jan 21, 2011, was champagne being uncorked in the Blue Jays front office when they traded Vernon Wells and his seven-year, $126 million dollar contract to the Los Angeles Angels of Anaheim. 

    With four years and $86 million remaining on what is often described as the worst contract in baseball, the Angels decided they wanted a piece of that action. Wells was up for the job, batting .218 with 25 homeruns and 66 RBI’s. 

    That’s 66 RBI’s at the bargain basement price of $403,680 each.

23. Paul Soliai, Miami Dolphins

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    Utah nose tackle Paul Soliai was drafted in the fourth round by the Dolphins in 2007.

    Despite starting just 20 games in his first four seasons, the ‘Fins decided to franchise Soliai in 2011; earning him the average of the top five salaries at his position for the season—$12.4 million.

    Soliai had a mediocre four seasons with the Dolphins before they slapped the franchise tag on him, and in 2011, he had the worst season he’s ever had as a full-time starter. 

22. Ben Gordon, Detroit Pistons

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    In 2009, the Pistons signed guard Ben Gordon to a five-year deal worth $55 million.

    Even at the peak of his career in Chicago, Gordon was an inefficient scorer with no interest in passing or rebounding; but at least he averaged 20 points per game and played 35 minutes.

    Since signing his $10+ million per year deal in Detroit, Gordon’s points per game average has dropped to 12 points per game, and he averages just 27 minutes per game.

21. Javon Walker, Oakland Raiders

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    It’s no secret the Oakland Raiders love to dump a piss-ton of money on players as a reward for one good season, a great 40-yard dash time, or some other reason unknown to the rest of the world.

    This is especially true when it comes to wide receivers--Javon Walker is a great example of this phenomenon. Riding the momentum of a 1,382 yard, 12 touchdown season in 2004, Walker left Green Bay for Denver, before scoring a six-year, $55 million dollar deal with the Raiders in 2008.  

    He sure paid dividends over two season with his 15 total receptions and one touchdown in 11 games.

20. Andrew Bynum, Los Angeles Lakers

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    Perhaps trying to recreate that Kobe (selected 13th overall) high school magic, the Lakers drafted center Andrew Bynum (selected 10th overall) right out of high school in 2005.

    Bynum was okay for the Lakers, but the injury prone center certainly didn't live up to expectations. After improving in his second year, the Lakers signed Bynum to a four-year deal worth $58 million in 2008.

    Since then Bynum has shown marginal improvement, but he’s nowhere near where a guy who is pulling in $14.5 million a year should be.

19. Mark Sanchez, New York Jets

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    In January 2011, quarterback Mark Sanchez led the Jets to an unlikely playoff victory against the division foe Patriots, advancing the team to their second AFC Championship game in as many years. That was the peak of an otherwise disappointing year for Sanchez—the next 11 months were almost entirely downhill for the embattled QB.

    Sanchez has started three seasons for Gang Green and, over that period, the only thing that has grown is the size of his paycheck. In 2009, Sanchez ranked 28th among QB’s in the league—in 2010, he ranked 27th and in 2011, he ranked 23rd.

    Despite showing only marginal improvements in his game over the years, Sanchez was the third highest paid QB in 2011. Sanchez raked in $14.25 million in 2011—compare that to Panthers rookie Cam Newton, who ranked 15th among QB's and earned $10 million less than Sanchize.

18. Brian Roberts, Baltimore Orioles

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    What if I told you a career .281 batter who hit 84 homeruns in 11 seasons, and somehow managed to give himself a concussion by whacking himself in the head with his own bat after a strikeout, earned $10 million dollars a year.

    Would you believe me?

    Of course you would! This is Major League Baseball afterall. The Orioles gave Brian Roberts a four-year, $40 million dollar contract extension in 2010.

    Drink it in and remember it the next time you're paying for some late night snacks with a bag of nickles.

17. Carson Palmer, Oakland Raiders

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    After losing starting quarterback Jason Campbell in October 2011, the Raiders traded away two high draft picks to the Bengals in exchange for Carson Palmer.

    Nevermind that the disgruntled Palmer hadn’t played football for almost a year. Nevermind that they mortgaged the entire future of the franchise for an aging QB who had never won a playoff game.

    The deal turned out just as bad, if not worse, for the Raiders than everyone expected. Palmer finished the season as the 19th ranked passer and was among the leaders in interceptions.

    The Raiders didn’t make the playoffs, but they did win the honor of paying Palmer $14 million.

16. Samuel Dalembert, Philadelphia 76ers

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    In 2001, the 79ers drafted Samuel Dalembert out of Seton Hall and in 2005, they signed him to a six-year deal worth $58 million—hoping he’d develop into a player good enough to earn that kind of money.

    He didn’t.

    After signing the deal, Dalembert actually had his two most productive seasons, before experiencing a sharp decline in 2008-09. Dalembert earned $12.2 million in his last season with the Sixers, a bit much for his eight points, eight rebounds and 24 minutes of playing time per game.

    He was traded to the Kings in 2010.

15. Barry Zito, San Francisco Giants

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    It might seem harsh to call Giants pitcher Barry Zito, dollar-for-dollar, one of the worst pitchers ever—but dollar-for-dollar pitcher Barry Zito is one of the worst pitchers ever.

    It doesn’t even feel right to dignify this all with further discussion, but Giants fans know what I’m talking about here.

14. Antonio Bryant, Cincinnati Bengals

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    What do you get when you combine Freddie Mitchell with Terrell Owens? Antonio Bryant.

    The troubled wide receiver out of PITT never lived up to his potential, as he dealt with off-the-field issues, inconsistency on the field, and injuries. After proving that he is unreliable with multiple teams, the always astute Bengals handed Bryant a four-year, $28 million dollar deal in 2010.

    Personal issues aside, the major problem was that Bryant had a serious knee issue. He never played a down, and his contract was eventually terminated; the Bengals ate $6.95 million in guaranteed money in the process.

13. Kosuke Fukudome, Cleveland Indians

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    In December 2007 the Chicago Cubs won a bidding war for free agent Chunichi Dragons star Kosuke Fukudome, signing him to a four-year, $48 million dollar deal. 

    Fukudome came to the windy city under high expectations underwritten by a big-time MLB contract, and failed to live up to expectations. That's just the Cubs way. (Well it was--Theo Epstein is going to patch the hole in that Titanic)

    Batting .260 with just 37 home runs and 169 RBI’s in about 3.5 seasons with the Cubs, the underachiever was traded to the Indians in August 2011.

12. Erick Dampier, Dallas Mavericks

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    In 2004, despite a largely mediocre eight year career, the Mavericks signed Erick Dampier to a seven year deal worth $73 million.

    Before finally waiving him in September 2010, the Mavs paid Dampier just over $10 million per season to net them about seven points in the 25 minutes he played per game.

11. Ilya Kovalchuk, New Jersey Devils

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    You know you’re an overpaid professional athlete when your absurd contract becomes the symbol for the kind of ludicrous deal-making that haunts bad teams and threatens the very existence of the salary cap.

    After a bidding war that would make Major League Baseball proud, free agent left-winger Ilya Kovalchuk inked a 15-year, $100 million dollar deal in 2010 to stay with the New Jersey Devils. The Russian player celebrated his historic contract with a 31 goal, -25 season—10 less goals from the season before.

    Well at least he has until 2025 to improve on his performance and earn his money.

10. Jake Delhomme, Carolina Panthers

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    After a medicore career, Panthers quarterback Jake Delhomme turned in the worst performance of his life in the 2009 NFC divisional playoffs against the Cardinals.

    The Panthers rewarded Delhomme with a five-year contract exension worth $42.5 million.

    Delhomme never rebounded from that interception extravaganza, and was released in March 2010. He then signed a two-year deal with the Browns before being released in July 2011.

9. Steve Francis, New York Knicks

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    In the 2006-07 season, Knicks guard Steve Francis raked in an impressive $15 million in salary.

    Not too bad for a guy scoring 11 points, 3.5 rebounds and averaging 28 minutes per game! Well, it was good for him, but less so for the Knicks.

    The Knicks finished 33-49 that season.

8. Stephon Marbury, New York Knicks

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    In the 2006-07 season, Knicks point guard Stephon Marbury raked in an impressive $17 million in salary.

    Not too bad for a guy socring 16 points, 3 rebounds and averaging 37 minutes per game! Well it was good for him, less so for the Knicks.

    The Knicks finished 33-49 that season.

    Déjà vu. 

7. Jayson Werth, Washington Nationals

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    For a few years the Washington Nationals looked and spent money like a National League bottom-dweller.

    In 2010, the Nationals decided it was time to lose a lot of games and spend a lot of money, with Jayson Werth as the flag-bearer of their new model.

    Signed to a seven-year, $126 million dollar contract, the career .274 hitter stunk up the nation’s capital by batting .232, with 20 home runs and 58 RBI’s in 2011. At least he was voted 4th most overrated player by his peers...oh wait.

6. Roy Williams, Dallas Cowboys

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    Roy Williams is one of the most overrated, under-producing wide receivers in NFL history. After a promising start to his career in Detroit, Williams was traded to the Cowboys for a first, third and sixth-round pick in the 2009 NFL Draft.

    After his arrival in Big D, Williams agreed to a six-year, $54 million contract, with $26 million guaranteed.

    Williams called his experience in Dallas “a nightmare,” and the feeling was mutual—he was released in July 2011. That's right, in the world of Roy Williams, raking in $26 million dollar as a useless fourth receiver is a "nightmare." 

    Williams went on to disappoint in Chicago. Wonder who will overpay Williams to consume oxygen in 2012...

5. Kirk Ferentz, Iowa

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    Nick Saban, Bobby Petrino, and Steve Spurrier. All three landed NFL head coaching gigs during the height of their college football careers. Not too long ago, many thought Kirk Ferentz would be included in that exclusive club. 

    In the mid-2000s every time an NFL head coach was fired from a bad team, the Iowa coach’s name would come up. However, he may never get a chance to fail as an NFL head coach. 

    Despite being the fifth highest paid coach in college football at $3.78 million dollars per year, Ferentz has only gone 57-47 in the Big Ten, last winning the conference in 2004.

4. Nick Collison, Oklahoma City Thunder

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    In 2003, the Oklahoma City Thunder (then Seattle SuperSonics) drafted Nick Collison out of Kansas.

    In 2006, they signed the zero-time All-Star to a five-year contract worth $33 million. Collison was at the peak of his career—averaging 10 points, nine rebounds and playing nearly 30 minutes per game.

    Collison production has declined steadily since signing that contract and in 2010-11, he averaged 4.5 points, 4.5 rebounds and 21 minutes per game. Totally worth the $13.25 million he was paid that season, right?

3. John Lackey, Boston Red Sox

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    As if being paid way more than what your performance deserves weren’t bad enough, John Lackey found a way be a public relations nightmare for the Boston Red Sox too.

    Lackey went 102-71 with a 3.81 ERA in eight seasons with the Angels, before signing a five-year, $82.5 million dollar deal with the Red Sox in 2009. 

    Lackey promptly made Boston regret the decision, with a 6.63 ERA over two seasons. He was also accused of crushing beers and fried chicken in the clubhouse during the Red Sox collapse in 2011.

    Mercifully, Lackey will have Tommy John surgery and won’t pitch in 2012.

2. Albert Haynesworth, Washington Redskins

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    In early 2009, Titans defensive tackle Albert Haynesworth was the most coveted NFL player on the free-agent market. Naturally, the Redskins came in first in the contest to see who would overpay this talented—but more trouble than he’s worth—player.

    The ‘Skins inked Haynesworth to a seven-year deal worth approximately $100 million, with $41 million guaranteed. To say Daniel Snyder didn’t get what he paid for in this deal would be an understatement.

    Haynesworth was almost immediately unhappy about switching to a 3-4 defense, and in a radio interview in September 2010, he explained that the $100 million contract hadn't affected his work ethic, despite rumors of being hungover in practice, dogging it in drills, showing up late to meetings and feuding with teammates.

    Haynesworth was traded to the Patriots in August 2011 but walked out of Washington with $36 million for his two seasons with the ‘Skins, having only played 20 games.

    Let’s break that down for a little perspective on the scale of wretchedness:

    Per Season: $18,000,000
    Per Game: $1,800,000
    Per Sack: $5,538,461
    Per (Solo) Tackle: $857,142

1. JaMarcus Russell, Oakland Raiders

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    The Raiders drafted quarterback JaMarcus Russell out of LSU in April 2007 and in September signed him to the richest rookie contract in NFL history.

    Over the next three seasons, Russell repaid the Raiders with some of the most lackluster, ineffectual and straight-up awful quarterback play ever for an early round draft pick.

    Russell signed a six-year, $61 million contract, with $32 million guaranteed. He lasted just three seasons with the Raiders, playing 31 games, before being cut. Ultimately he walked away with $40 million.

    Let’s break that down for a little perspective on the scale of wretchedness:

    Per Season: $13,333,333
    Per Game: $1,290,322
    Per Touchdown: $7,777,777
    Per Completion: $112,994