NBA Free Agency: 9 Most Regrettable Signings of the Last Decade

Stephen Babb@@StephenBabbFeatured ColumnistJuly 30, 2012

NBA Free Agency: 9 Most Regrettable Signings of the Last Decade

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    Not every free-agent signing works out as planned. 

    Sure, some general managers always seem to get it right. Some know a good deal when they see it or all the warning signs other guys miss.

    Then, there are decision makers like Isiah Thomas who almost single-handedly set the New York Knicks back a good five years.

    In a decade that saw more than its fair share of overspending, a handful of deals stand out as the worst offenders. Some of the deals were signs of desperation. Others were just a product of bad judgment.

    And, still others simply met with bad luck; predicting injuries isn't always a science.

    Here are the nine free-agent acquisitions that stirred up the most regret over the last 10 years.

Raef LaFrentz-2002

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    After three-and-a-half solid seasons with the Denver Nuggets, Dallas Mavericks owner Mark Cuban apparently thought he'd witnessed the NBA's next big thing.

    Instead, he made Raef LaFrentz its next big flop.

    The 6'11" forward-center got a seven-year, $70 million contract to stay with the Mavericks, who had acquired him from the Nuggets the previous season before the trade deadline. He spent just one season with the Mavericks before the Boston Celtics got suckered into trading for him.

Erick Dampier-2004

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    Brendan Haywood wasn't the first big man on whom Mark Cuban spent way too much.

    That honor belongs to Erick Dampier (and before him, Raef LaFrentz), who received a seven-year, $70 million pact after coming fresh off of a double-double average in his most recent campaign with the Golden State Warriors.

    In six seasons with the Dallas Mavericks, Dampier never averaged double-digit points or rebounds—though he remained a solid rebounder, in general.

    Cuban seemed so sold on getting a big man to rectify the Mavs' wayward defense that he was willing to let Steve Nash walk that summer. It appears even the best businessmen don't always make the right investment.

Bobby Simmons-2005

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    The summer after receiving the NBA's Most Improved Player honors brought good things for swingman Bobby Simmons.

    Five years and $47 million worth of good things to be exact.

    It brought an expensive headache to his new employers, the Milwaukee Bucks. Simmons held up well enough in his first season, averaging over 13 points in 2005-06. His production steeply declined thereafter, and Simmons didn't remain with the Bucks for long.

    If only there were an award acknowledging the exact opposite of the NBA's Most Improved Player.

Jerome James-2005

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    Jerome James had one good playoff series.

    Just one.

    He'd literally done nothing else in his previous five seasons to justify a five-year, $30 million deal. But that didn't stop Isiah Thomas from giving him just that.

    The guy really knows how to spot talent, doesn't he?

    James spent four years with the Knicks, never averaging more than three points, 2.1 rebounds or nine minutes per game.

Eddy Curry-2005

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    As if taking a mindless risk on Jerome James weren't enough, Isiah Thomas inked the even bigger Eddy Curry to an even bigger deal.

    Surprise, surprise—he was an even bigger disappointment, a six-year, $60 million disappointment.

    Curry did have three productive seasons in New York, albeit seasons in which he didn't rebound or play a lick of defense. Curry spent just two more seasons with the Knicks, playing in a total of 10 games.

    Yes, that comes out to $1 million per game for those two campaigns.

Ben Wallace-2006

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    Ben Wallace has had a long, steady and admirable career. Despite having virtually no scoring ability whatsoever, he proved himself a defensive stalwart and an exceptional rebounder during the Detroit Pistons' resurgence in the early 2000s.

    The Chicago Bulls bought into the hype just a bit too much, in fact.

    They bought in to the tune of four years and $60 million.

    As Wallace lost a step into his 30s, already one-dimensional production quickly disappeared. After two disappointing seasons in Chicago, the four-time Defensive Player of the Year was traded to the Cleveland Cavaliers.

Rashard Lewis-2007

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    Rashard Lewis had an excellent career with the Seattle Sonics, but it's hard to understand what the Orlando Magic were thinking when they orchestrated a sign-and-trade deal that paid him $118 million over the course of six years.

    Lewis' production and relevance steadily declined; and after four seasons with the Magic, he changed places with the similarly overpaid Gilbert Arenas.

    After the first two years of his deal, the sharpshooting forward never averaged more than 14.1 points in a season.

    That's certainly not what you expected from a guy making $20 million a year.

Gilbert Arenas-2008

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    The Orlando Magic didn't sign Gilbert Arenas to his six-year, $111 million deal—they just got stuck with it before amnestying him with three more years remaining on the nightmare of a contract.

    Instead the Washington Wizards own the distinction of re-signing Arenas to the insane deal after five productive seasons with the team. Arenas had proven himself to be one of the most lethal guards in the league.

    Before his career was derailed by injuries and off-the-court distractions, Agent Zero was a dynamic scorer from anywhere and a decent distributor to boot. Now just 30 years old, though, this guy has become an afterthought in the NBA.

    He played in just 17 games last season, rarely getting off the bench for the Memphis Grizzlies.

Joe Johnson-2010

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    The Atlanta Hawks were desperate to retain a franchise player when they re-signed shooting guard Joe Johnson to a six-year deal worth almost $120 million.

    Johnson proved be a fine player during his stint with Atlanta—and even a six-time all-star.

    But, he was not a franchise player, and his production has steadily declined since inking the deal. More than a few teams would like to have a guy like Johnson on board, and that's precisely why the Brooklyn Nets traded for him this summer in a bid to give Deron Williams some help.

    Johnson is not, however, in the same league as LeBron James, Kobe Bryant or Dwyane Wade.

    He shouldn't be making $20 million a year.