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Every NBA Team's Worst Contract of All Time

Though we have yet to complete the first quarter of the NBA season, there is already fierce speculation about the status of certain big name free agents, as teams attempt to seduce high profile players with the prospect of a record-setting, lucrative contract. Speculation has been rampant, for example, about the interests that many teams have in free agent to be Kevin Durant. But Durant is not the only All-Star player on the brink of free agency. The NBA enters a big contract year for many of its most talented players. This leaves GMs across the league scrambling to decide which players deserve the big money contracts and which ones to avoid. This is the battle every year, and one that often makes or breaks the careers of professional sports executives. Some, of course, have been more successful than others.

Golden State Warriors general manager Bob Myers was named the 2015 executive of the year after making some key personnel decisions that aided in the Warriors' NBA championship run. And he may be in line to garner the prize again, as his offseason signing of Draymond Green to a new deal (5 years, $82 million), slightly under his potential max, is already paying huge dividends. The Warriors had a historic start to this season and Green is putting up All-Star caliber numbers. This seems to be the perfect example of a smart free agent signing.

Consider, in contrast, the Dallas Mavericks' signing of Wesley Matthews. Coming off of a brutal, season-ending injury last year, Dallas signed the shooting guard to a 4 year, $70 million contract and it is fair to say that he has failed to meet expectations. Though the season is still young, Matthews is failing to match his career average in literally every statistical metric. The Mavericks are certainly not the first team to make a poor free agent signing, and this particular contract probably won't go down as their worst decision. To demonstrate, I've chosen to look at the worst contract decision in the history of each NBA franchise. Who paid the biggest bucks for the worst output? I've sorted the list alphabetically by team, so you can judge for yourself which decision ranks as the worst of all time.

31 Atlanta Hawks - Jon Koncak

via thehoopdoctors.com

30 Boston Celtics - Travis Knight

via joshatkins.com

29 Brooklyn (New Jersey) Nets - Jayson Williams

via espn.com

28 Charlotte Hornets (Bobcats) - DeSagana Diop

via nba.com

27 Chicago Bulls - Ben Wallace

via zimbio.com

26 Cleveland Cavaliers - Larry Hughes

via businessinsider.com

An unwitting future trade partner of Chicago, the Cavs managed their own high profile free agent signing in 2005 when they inked Larry Hughes to a five year, $70 million deal. Hughes was a lottery pick in the 1998 draft and showed flashes of All-Star quality play that just never fully materialized. After averaging 22 points-per-game in Washington, the Cavs made the investment, but his numbers steadily (and rapidly) declined during his time in Cleveland before they shipped him to Chicago in 2008. While a $70 million deal may not seem ludicrous for a guy that averaged just over 14 ppg for his career, consider that the reigning NBA MVP, Stephen Curry, is only halfway through a four-year, $44 million deal.

25 Dallas Mavericks - Erick Dampier

via wikimedia.org

24 Denver Nuggets - Kenyon Martin

Jerome Miron-USA TODAY Sports

23 Detroit Pistons - Charlie Villanueva

Jerome Miron-USA TODAY Sports

22 Golden State Warriors - Adonal Foyle

via nba.com

21 Houston Rockets - Scottie Pippen

via cimcontent.com

20 Indiana Pacers - Jermaine O'Neal

Jed Jacobsohn /Allsport

19 Los Angeles Clippers - Baron Davis

Kirby Lee-USA TODAY Sports

18 Los Angeles Lakers - Steve Nash

Jayne Kamin-Oncea-USA TODAY Sports

17 Memphis/Vancouver Grizzlies - Bryant Reeves

via grizzlybearblues.com

16 Miami Heat - Brian Grant

via yahoosports.com

15 Milwaukee Bucks - Bobby Simmons

via nba.com

Simmons is a strange story. He had one good season with the Clippers and Milwaukee dropped a four-year, $47 million deal in his lap. I suppose we can applaud the Bucks for taking a risk on a player that may have finally started to show his true potential. Unfortunately they were wrong. Simmons never matched his numbers from the 2004 season and left Milwaukee after just two seasons.

14 Minnesota Timberwolves - Michael Olowokandi

via nba.com

13 New Orleans Pelicans - Eric Gordon

Derick E. Hingle-USA TODAY Sports

12 New York Knicks - Stephon Marbury

Jeff Zelevansky / TheNYPost

Selecting just one bad contract is difficult for a team that has, arguably, FIVE of the worst deals in NBA history. Marbury represents one of the many contract gaffes. He was a baller for several years, making All-Star games while playing in both New Jersey and Phoenix, but the Knicks grabbed him right as he began his slide into obscurity. Marbury signed a four-year, $76 million deal in 2003 and was shipped off to the Knicks. They started paying that deal in 2005 but injuries and age limited his play time and his consistent 20+ per game numbers took a nosedive. Now he's collecting checks as a "professional basketball player" in China.

Honorable mentions:

Amar’e Stoudemire – 5 years, $99 million

Jerome James – 5 years, $30 million

Eddy Curry – 6 years, $56 million

11 Oklahoma City Thunder (Seattle SuperSonics) - Vin Baker

via theseattlesalmon.com

Vin Baker was a very talented big man early in his career, putting up 20 and 10 numbers in Milwaukee. The Sonics inked him to a 7-year, $86 million deal in 1999 (a huge contract for the time) and things took a turn for the worse. His playing time and numbers both declined steadily until he left for Boston in 2002. Apparently his financial planning began to match his poor play. He blew his multi-millions and now works at a Starbucks.

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9 Orlando Magic - Rashard Lewis

Bob Donnan-USA TODAY Sports

8 Philadelphia 76ers - Elton Brand

via wikimedia.org

7 Phoenix Suns - Penny Hardaway

via rarevintagewear.com

6 Portland Trailblazers - Darius Miles

via slamonline.com

5 Sacramento Kings - Francisco Garcia

via bleacherreport.com

4 San Antonio Spurs - Richard Jefferson

Tom Szczerbowski-USA TODAY Sports

3 Toronto Raptors - Antonio Davis

via pinterest.com

2 Utah Jazz - Andrei Kirilenko

Brad Penner-USA TODAY Sports

1 Washington Wizards - Gilbert Arenas

via triangleoffense.com

Coincidentally, this last contract may very well be the worst in NBA history. Arenas was an outstanding, All-Star player for several seasons and had one of the most abrupt exits from the league in NBA history. The Wizards offered him a six-year, $111 million conract in 2008 and things all went downhill. He was suspended by the NBA, had a series of (potentially faked) injuries, and set personal records for futility before being shipped off to Orlando two years later. To seal the deal, even Arenas admitted (in an interview) that his deal may have been the worst contract ever.

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Every NBA Team's Worst Contract of All Time