The 20 Worst NBA Contracts Ever

Today marks the end of the NBA’s self-imposed moratorium, which means all the rumored signings and trades can now become official. (July 1 marked when teams could start talking to free agents and come to terms on handshake deals.) Free agency is one of the most exciting parts of the NBA offseason; fans watch anxiously to see what new players may soon suit up for them. However, general managers and front offices don’t always make smart choices. Through the years, there were signings that either at first glance or in retrospect had many scratching their heads in confusion. Lets take a look at the 20 worst free agent signings in NBA history. (WARNING: Knicks fans may not want to read on)

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VIN BAKER (Sonics: seven years, $86.7 million)
Following the first four years of his career, Vin Baker looked like a quality power forward, capable of getting 20 points and 10 rebounds in any game. In 1997, the Seattle Supersonics traded for Baker and awarded him with a brand new contract as well. However, during his five seasons in Seattle he would never average 20 points or 10 rebounds again. In fact, Baker’s career was sadly derailed by his bout with alcoholism.

STEPHON MARBURY (Knicks: four years, $76 million)
The first of many bad decisions made by then GM Isiah Thomas was re-signing Stephon Marbury after acquiring him from Phoenix the season before. After an initial foray into the playoffs, which concluded in a first round loss, the Knicks failed to make the playoffs again during the final four years of Marbury’s contract. Marbury would ultimately be out of the NBA for good following a failed 2008-09 season with the Boston Celtics.

TRAVIS KNIGHT (Celtics: seven years, $22 million)
Rick Pitino‘s climb from college coach to NBA coach wasn’t pretty and the signing of Travis Knight is one of the reasons why the transition didn’t go too well. After a rookie season where Knight averaged 4.8 points and 4.5 rebounds per game, the Celtics tossed $22 million his way in hopes he would be their man in the middle for years to come; yet years turned into a year. Knight only wore Celtic green for one season, where his numbers only slightly improved to 6.5 points and 4.9 boards.

PENNY HARDAWAY (Suns: seven years, $87 million)
Anfernee “Penny” Hardaway was one of the best and most polarizing players in the NBA during his time with the Orlando Magic. An athletic 6-7 point guard, Hardaway had his way in the league and at the height of his career, posted averages of 21.7 points, 7.1 assists, 2.0 steals and 4.3 rebounds a night. However, in the 1999 offseason, the Phoenix Suns offered a behemoth of a contract to Penny even though his best days were behind him. A knee injury in 1997 lingered on until he ultimately needed microfracture surgery during the 2000-2001 season. He would only play in 202 out of a possible 328 games as a Sun.

BOBBY SIMMONS (Bucks: four years, $47 million)
Bobby Simmons burst onto the NBA scene in the 2004-05 season where he was named the Most Improved Player, an award that definitely helped drive his value up in free agency. Simmons played in the third-most games, started the second-most and scored the third-most points on one of the more dysfunctional Los Angeles Clippers team in recent memory on his way to receiving the MIP award. The Milwaukee Bucks decided to overlook that and threw $47 million at him so he would leave L.A. Yet Simmons was never the player the Bucks thought they were getting and he would average a mere 10.6 points during his two-year stint in Milwaukee.

ALLAN HOUSTON (Knicks: six years, $100 million)
Allan Houston is a player that will be beloved by Knicks fans for years to come, especially due to his heroics against the Miami Heat in the series-deciding Game 5 of the 1999 NBA Playoffs. However, the contract he received two years later is one that haunted the New York Knicks franchise even after Houston retired in 2005. At the age of 30, Scott Layden and the Knicks thought it was wise to give Houston $100 million over the next six seasons, but Houston would only play four more years and ended up collecting $40 million from New York even after he had called it quits.

ERICK DAMPIER (Mavs: seven years, $70 million)
In a case of Mark Cuban overspending to try and fill the void with a big-name, high-contract player, the Mavericks signed Erick Dampier for an unreal $70 million (if you want evidence why the owners were crying wolf about losing money during the 2011 lockout, then look no further than contracts like this one). Dampier had a long, mediocre stay with the Mavs before bolting to the Heat.

ANTONIO DAVIS (Raptors: five years, $60 million)
You know who deserves $12 million a year in the NBA for five years? Not that many players as evidenced by some of the contracts that we’re seeing this summer, but definitely not 33-year-old rebounding specialists. After getting his first and only All-Star appearance, Antonio Davis hit it big with a $60 million contract. However, after his big payday, the 6-10 center never reached the 10 rebound plateau ever again.

TIM THOMAS (Bucks: six years, $67 million)
Tim Thomas was never the type of player that you would associate with the NBA’s elite, but he got paid like he was. There is no good reason for any team to pay him over $11 million a year like the Bucks did in 2000. Before signing with Milwaukee, Thomas’ highest scoring average was 11. Thomas would never live up to the contract but he would travel a lot… and we’re talking about his journeyman status that led him on a cross-country tour during his 13-year career.

BRIAN GRANT (Heat: seven years, $86 million)
In 2000, the Heat gave Brian Grant, a guy who up to that point averaged less than 10 points and 10 rebounds per game, a deal worth $86 million. I don’t know why anyone in their right mind would do such a deal. Miami boss Pat Riley called the forward the missing piece to the championship puzzle. Sadly for Grant, he was traded to the Lakers in 2004, the year after the Heat got the real missing piece to their puzzle, a guard from Marquette by the name of Dwyane Wade.

BEN WALLACE (Bulls: four years, $60 million)
Defense wins championships, as the saying goes, but did you know that it also nets certain players outlandish and undeserved contracts too? Case in point, Ben Wallace, who is known strictly for picking up boards and blocking shots, and received an uncalled for $60 million offer from the Chicago Bulls when it was obvious he was losing more than a few steps. Wallace quickly signed on the dotted line and went into autopilot for the rest of his career. That’s the way most would explain his less-than-spectacular rebounding and shotblocking numbers once he left Detroit.

RAEF LaFRENTZ (Mavs: seven years, $70 million)
Raef LaFrentz could easily have made this list twice — first for his deal with the Mavericks worth $70 million and second, for the one-year contract he signed with the Trail Blazers for $12.7 million. LaFrentz has suckered the NBA into believing that his talent is worth the high price tag and both of these contracts again point to why the 2011 lockout brought such stiff changes to the Collective Bargaining Agreement.

DARIUS MILES (Blazers: six years, $48 million)
The Trail Blazers felt they had a diamond in the rough in forward Darius Miles when they signed him to a six-year deal worth $48 million when he was only 22 years old (the Los Angeles Clippers felt the same way when they drafted Miles straight from high school; both teams were wrong). What they got was more like sterling silver. He and former coach Maurice Cheeks never saw eye-to-eye and for all his athleticism and talent, Miles made a whole lot of money for collecting bench splitters. He also cost Portland an extra $18 million in salary cap space when he came back from the dead for 34 games with Memphis in 2008-09.

LARRY HUGHES (Cavs: five years, $70 million)
Larry Hughes was given a lucrative deal in an effort to make him the Robin to LeBron James‘ Batman… and people wonder why King James bolted for South Beach as quickly as he could. What eventually happened though was Hughes’ constant injuries caused him to miss 58 total games in his two full seasons as a Cleveland Cavalier. His 15.2 points per game average as a Cav was solid, but definitely not Robin-worthy.

AUSTIN CROSHERE (Pacers: seven years, $51 million)
Playing well during the postseason can make a world of a difference when it comes to the amount of money in a player’s pockets. Austin Croshere averaged 6.8 points per game in his entire NBA career, but during the Pacers’ 2000 Playoff run, Croshere spiked his production up to 10.8 points and 5.0 rebounds a night, good enough numbers to get him a brand new and highly lucrative contract that offseason with Indiana. The following season, Croshere went back to his mediocre ways and the Pacers management was stuck with a $51 million problem for six more seasons.

GILBERT ARENAS (Wizards: six years, $111 million)
Gilbert Arenas was the Wizards organization for a good three to four seasons, hitting countless buzzer-beaters and game-winners, leading the Wizards to the playoffs three times and being named an All-Star three times. After playing only 13 games the previous season, Arenas somehow milked Washington for $111 million in 2008 (which, amazingly, was less than he was originally offered). For his part, Agent Zero would only play 55 games as a member of the Wizards for the next three seasons.

EDDY CURRY (Knicks: six years, $60 million)
By the end of his career, Eddy Curry was known more for his big contract and, at times, even bigger waistline than his actual on-court abilities. Once again, leave it to the New York Knicks to give him a contract that he was incapable of living up to. Interesting fun fact: for his career, Eddy Curry is a 100 percent three-point shooter. Maybe the Knicks thought he would revolutionize basketball with his touch from deep. His final two seasons as a Knick saw him play a mere 10 games (even Andrew Bynum laughs at this signing).

JIM McILVAINE (Sonics: seven years, $33 million)
Initially, Jim McIlvaine was anointed as the “Shaq Stopper.” It overshadowed his lack of offensive skills (for example, the fact that he averaged only 2.3 points and 2.9 rebounds for the Washington Bullets). But the title of “Shaq Stopper” must have caused the Sonics to overeagerly offer him $33.6 million and trade away “The Reign Man” Shawn Kemp. As a consolation prize, the fans in the upper northwest did eventually get to watch Kevin Durant don the Sonics green and yellow for a year.

JEROME JAMES (Knicks: five years, $30 million)
In the 2005 NBA Playoffs, Jerome James posted averages of 12.5 points and 6.8 rebounds in 11 games. So of course, this small scale of consistency was enough for Knicks general manager Isiah Thomas to ignore the fact that James had career averages of 4.9 points and 3.5 rebounds. What did Thomas pay James, you ask? He gave him $30 million. After hitting it big, James showed up to camp out of shape, and ended up playing a total of five minutes in his first season with New York. The following year, he played two games before suffering a season-ending injury. I tried to warn Knick fans that this list wouldn’t be pretty.

JON KONCAK (Hawks: six years, $13 million)
If you want to find the most absurd free agent contract ever signed, look no further than this contract, signed 22 years ago. The Hawks paid Koncak just over $2 million per season starting back in ’89. While that may be considered chump change in the NBA these days, at the time it was more than guys like Michael Jordan, Magic Johnson and Larry Bird made. Those three guys are easily top five, dead or alive all-time. Koncak, on the other hand, didn’t even average five points for his career.

Which contracts have you seen that are utterly indefensible?

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