The 15 worst free agent contracts in NBA history

Now the the NBA’s moratorium on free agent signings has been lifted, players are finally inking their long anticipated new contracts. While this might not be much of a comfort to fans out there, given this history of awful deals in the league there’s a really good chance your favorite team’s general manager has absolutely no idea what he’s doing.

Now that the NBA’s free agency frenzy is in full swing, it’s a good time to give you our list of the 15 worst free agent contracts in NBA history.

Austin Croshere

15. Austin Croshere, Indiana Pacers in 2000 (seven years, $51 million)

I have no idea how the Pacers got suckered into this one. During Indiana’s 2000 playoff run, Croshere averaged 9.4 points and 4.7 rebounds off the bench. So naturally he deserved a huge contract, right? For the next seven years the Pacers tried to prove they hadn’t made a mistake, but Croshere averaged just 7.0 points and 4.1 rebounds per game in 467 contests. He only started 74 of those games.

Croshere was a soft 6-9 forward who could shoot a little, but not enough to get you excited about his talent. He pretty much just took up space on Indiana’s bench for seven years after signing.

Peja Stojakovic

14. Peja Stojakovic, New Orleans Hornets in 2006 (five years, $64 million)

Stojakovic was 28 when the Hornets decided to add him to their roster in the hope that surrounding Chris Paul with a shooter would put the team in the hunt for a title. It didn’t work out that way. He arrived in 2006 and played just 13 games thanks to lingering back issues. When he returned he was nothing more than an average starter, and during his time with the Hornets he averaged 14.5 points per game.

He was traded to the Toronto Raptors at the beginning of the 2010 season, but was released in January of 2011.

Raef LaFrentz

13. Raef LaFrentz, Dallas Mavericks in 2002 (seven years, $70 million)

LaFrentz was a decent role player for the Denver Nuggets, but when the Dallas Mavericks traded for him during the 2001-02 season they thought they had a franchise-type guy. They were wrong. That offseason they inked the 6-11 forward/center to a huge deal and for the next seven years he proceeded to weigh down three different payrolls.

He played just 69 games with the Mavericks and averaged 9.3 points per game, before being traded to the Boston Celtics, who shipped him to Portland after three years. Over the length of his seven-year deal, LaFrentz averaged just 7.5 points and 4.8 rebounds per game.

Kenyon Martin

12. Kenyon Martin, Denver Nuggets in 2004 (seven years, $92.5 million)

After four years in the NBA, Martin had posted averages of 15.1 points, 7.6 rebounds, 2.4 assists, 1.3 steals and 1.4 blocks per game as a member of the New Jersey Nets. What did that get him? A sign-and-trade deal to the Denver Nuggets for a max contract.

While Martin did have unforeseen injury woes, when he saw the court during the seven years he was under contract he averaged just 12.3 points and 7.0 rebounds per game. He has been a serviceable player throughout his career, but he was never even close to a max contract player.

Gilbert Arenas

11. Gilbert Arenas, Washington Wizards in 2008 (six years, $111 million)

Agent Zero averaged 22.9 points, 4.2 rebounds and 5.5 assists during his first six seasons in the NBA, but he played in just 13 games during the 2007-08 season before becoming a free agent. Still, the Washington Wizards re-upped him for $111 million and watched that deal completely blow up in their faces. He was suspended for having a gun in the team’s locker room and pleaded guilty to a felony related to the case. He was later traded to the Orlando Magic, who kept him for 49 games before waiving him under the league’s amnesty provision.

Before being released by the Magic, Arenas avearged 15.0 points, 3.3 rebounds and 5.0 assists over the length of that contract.

How bad is his deal? Even after being amnestied by the Orlando Magic on December 9, 2011 and not playing in the NBA since 2012, Arenas will be the NBA’s third-highest paid player during the 2013-14 season. Only Dirk Nowitzki and Kobe Bryant will make more money.

Allan Houston

10. Allan Houston, New York Knicks in 2001 (six years, $100 million)

Houston joined the Knicks in 1996 after his rookie contract with the Detroit Pistons expired. Over the next five seasons he averaged 17.7 points, 3.3 rebounds and 2.5 assists per game. Those are nice numbers, but not so nice that you should give the guy $100 million at the age of 30.

Over the first two years of his gigantic deal, Houston averaged 21.5 points per game, but in his third year he started just 50 games and his averages dropped across the board. Then, at 33 during the 2004-05 season he played just 20 games and averaged 11.9 points. He was forced to retire in 2005 thanks to a knee injury.

Ben Wallace

9. Ben Wallace, Chicago Bulls in 2006 (four years, $60 million)

In 2006, Wallace was a four-time Defensive Player of the Year and a four-time All-Star, but at 32 years old he wasn’t in his prime. Still, the Bulls thought he had something left in the tank, so they inked him to a ridiculous deal. Before signing with the Bulls Wallace had averaged just 6.6 per game for his career. Wallace did help improve Chicago’s defense, but his numbers fell off rapidly and the Bulls quickly realized their mistake and traded him in the middle of his second season in town.

He was shipped to Cleveland, where he averaged 4.0 points and 7.5 rebounds in two seasons before being traded to the Phoenix Suns, who bought out the remainder of his contract.

Brian Grant

8. Brian Grant, Miami Heat in 2000 (seven years, $86 million)

Brian Grant was a crowd-pleasing big man during his first six years in the league with the Sacramento Kings and Portland Trail Blazers. He was an old-school banger on the inside who loved to mix it up physically. Seeking some toughness, the Heat gave a max contract to a guy whose career averages of 11.8 points and 7.5 rebounds should have been a turnoff. Instead, Pat Riley saw him as the missing piece of the puzzle for his Heat.

Grant played four years in Miami and averaged 11.0 points and 8.5 rebounds, far from the numbers a guy with a huge contract should produce. In the summer of 2004 he was traded to the Los Angeles Lakers as part of the deal that brought Shaquille O’Neal to Miami. After one season in LA (during which he averaged 3.8 points and 3.7 rebounds), the Lakers used their amnesty provision to rid themselves of his contract.

Vin Baker

7. Vin Baker, Seattle Sonics in 1997 (seven years, $86.7 million)

The Sonics acquired Baker from the Milwaukee Bucks in a three-team deal after the 1996-97 season and Seattle promptly signed him to a max contract. Baker averaged 21.0 points and 10.3 rebounds in his final season with the Bucks. He was solid in his first year with the Sonics, starting all 82 games and averaging 19.2 points and 8.0 rebounds. After that things began to fall apart and injuries took their toll.

Baker’s numbers steadily declined and he was traded to the Boston Celtics after four years in Seattle. After the 1998-99 lockout season Baker’s weight ballooned to almost 300 pounds, but while he got his weight down, he revealed that he was an alcoholic. After Baker was confronted by Celtics coach Jim O’Brien (who smelled alcohol on him at practice), he was suspended then released by the team.

Larry Hughes

6. Larry Hughes, Cleveland Cavaliers in 2005 (five years, $70 million)

Hughes was signed by the Cavs to be LeBron James’ wingman, let’s just say that didn’t work out as planned. Hughes had bounced around, playing with three teams before the Cavs signed him, but his 2004-05 season with the Washington Wizards made teams take notice. He averaged 22.0 points, 6.3 rebounds, 4.7 assists and 2.9 steals per game, and the Cavs had to have him. What they got was an albatross of a contract.

In his first two seasons with the Cavs Hughes regressed, averaging 15.1 points, 4.0 rebounds, 3.7 assists and 1.3 steals per game. His shooting touch also disappeared, as his field goal percentage dropped to 40.3 percent. Injuries and inconsistency plagued him over the rest of the contract that saw him spend with the Bulls then the Knicks. He never reached back to become the player he was in that final season with the Wizards.

Darius Miles

5. Darius Miles, Portland Trail Blazers in 2004 (six years, $48 million)

The Portland Trail Blazers traded for Miles midway through the 2003-04 season and thought they had a rising star. He was 22 that offseason and had averaged 10.9 points and 4.5 rebounds the previous year. He was given a huge payday and proceeded to only play two of the six seasons on his contract. He averaged 13.3 points in 103 games during that time, but then missed both the 2006-07 and 2007-08 seasons with a knee injury.

Miles refused to officially retire though, so the Blazers had to keep right on paying him. In 2009 he signed to play two games with the Memphis Grizzlies, just because he stepped on the floor, the Blazers took an $18 million hit to their salary cap. On top of that, Miles was a headcase who was constantly bickering with coaches and teammates

Eddy Curry

4. Eddy Curry, New York Knicks in 2005 (six years, $60 million)

Curry was 22 years old and coming off a season in which he averaged 16.1 points and 5.4 rebounds for the Chicago Bulls. Things were looking bright for him. But it was discovered that he had a serious heart problem and it would probably have been best if he had just retired. So, of course, Isiah Thomas locked him in to a monster contract that wasn’t insured.

He played in 222 games for the Knicks, and in his second season he was on the court for 81 games and averaged 19.5 points per game. Then he got comfortable and it was all downhill. Curry averaged 13.2 points in 59 games in 2007-08, then played in just 10 more games for the Knicks over the next two years before missing the entire 2010-11 season. Though he didn’t play that year, Curry earned $11 million.

Jerome James

3. Jerome James, New York Knicks in 2005 (five years, $30 million)

James was 29 and coming off season in which he averaged 4.9 points and 3.0 rebounds in Seattle. But a decent run in the postseason sent his stock soaring and Isiah Thomas had to have him. In four seasons with the Knicks, the 7-footer only played in 90 games and averaged a whopping 2.5 points and 1.8 rebounds per game. The contract doesn’t look as bad based purely on dollars, but the Knicks essentially paid $30 million for the equivalent of Mark Madsen. Only without the sweet dance moves and general likability.

Jon Koncak

2. Jon Koncak, Atlanta Hawks in 1989 (six years, $13 million)

I know you’re thinking that $13 million over six years isn’t that much money, but considering Koncak’s contract paid him more than Michael Jordan, Magic Johnson or Larry Bird, it’s a huge amount of money by the standards at the time. Before signing that deal, the 7-foot Koncak held career averages of 6.2 points, 6.1 rebounds and 1.0 blocks during his four years in the NBA. During the playoffs in 1989, he had a mini-breakout and averaged 12.8 points and 9.6 rebounds in five games. So obviously it was time to pay him big, right?

Over the six years of his deal, Koncak was even worse than he was before he signed the contract, as he averaged 3.6 pounds, 4.3 rebounds, 1.3 assists and 1.0 blocks in 21.3 minutes per game in 430 contests. Considering the time and his lack of production it’s hard not to list the man who became known as “Jon Contract” as one of the worst signings in NBA history.

Jim McIlvaine

1. Jim McIlvaine, Seattle Sonics in 1996 (seven years, $33.6 million)

McIlvaine played his first two NBA seasons for the Washington Bullets during which he averaged 2.1 points, 2.5 rebounds and 1.7 blocks in 12.8 minutes per game. He played in 135 contests, starting just six. But for some insane reason the Sonics saw him as a “defensive specialist” who could come in and help protect the rim as a starter.

Seattle was fresh off an NBA Finals appearance and was led by the All-Star duo of Gary Payton and Shawn Kemp, with Hersey Hawkins, Detlef Schrempf and Sam “Big Smooth” Perkins filling out the starting lineup. They thought McIlvaine was the missing piece to the puzzle. Against the objections of the entire sports world, they handed him a huge, inexplicable contract and quickly realized it would be an unmitigated disaster. What made it worse is that McIlvaine’s deal ticked Kemp off, since he was seeking an extension.

McIlvaine only lasted two years with the Sonics and averaged 3.5 points, 3.7 rebounds and 1.9 blocks in 16.8 minutes per game. He was traded to New Jersey in 1998 to give Seattle salary cap room, and he ended up playing three injury-riddled seasons with the Nets. With New Jersey he wound up averaging 2.2 points, 3.0 rebounds and 1.5 blocks in 14.2 minutes per game in 106 contests. The Nets bought out his contract after the 2000-01 season, and he retired shortly after that.

Others receiving votes: Stephon Marbury, New York Knicks in 2004 (four years, $76 million); Tim Thomas, Milwaukee Bucks in 2000 (six years, $67 million); Jermaine O’Neal, Indiana Pacers in 2003 (seven years, $126.6 million); Rashard Lewis, Orlando Magic in 2007 (six years, $118 million). 

About Ryan Phillips


  1. your missing one… He is currently playing for the Miami Heat..Rashard Lewis

    • Lewis was definitely in the “others receiving votes” category, but he just missed being put on the list. He was at least a serviceable player for most of that contract, but yes it was awful.

  2. Rashard Lewis was serviceable (6 years @ 118 million) yet Alan Houston (6 years @ 100 million) is on this list? Alan Houston was a top ten player in the league for back to back years during that contract, rashard Lewis wasn’t even the best player on his own team.

    Also, I’m not sure if you realize this or not, 6 year 35 million dollar nba contracts are so standard for below average bench players in the nba that I don’t even bat an eye at it. Are they being overpaid in general, sure, but what pro athlete isn’t?

    Mike dunleavy getting paid around 10 million a year by the pacers was one of the worst contracts ever…but rashard Lewis was the worst contract in nba history, it crippled the magic to this day.

  3. Lewis was undoubtedly an awful contract, but on Houston’s you have to consider the era too. No one made that much money back then. Also, the contracts in the $30 million range listed happened years ago when that wast standard practice. McIlvaine got one of the league’s biggest deals at the time, and Jerome James signed a deal way above what anyone else was willing to pay him and the Knicks got suckered in. They were essentially bidding against themselves. The same thing happened to the Blazers with Darius Miles. No one else trusted him enough to shell out that much money.

    • Where are you getting that $15-16 million contracts weren’t standard practice in 2001? Seriously…are you even a sports fan? First, you don’t know if the contracts are guaranteed…though you THINK they are…and then you act as if 2001 was 1985. Yes…even in 2001, pretty much any top team had at least one player making $15 million. Usually it was signing your own free agent, since (I am guess you don’t know this either) teams can sign their own free agents for whatever they want with no regard for the cap.

      Seriously…you yardbarket people should stick to what you know…posting pictures of female athletes as if they exist to suit virgins with pathetic blogs who know nothing about women or sports.

      • NBA contracts ARE guaranteed, but NOT if a player retires voluntarily. Houston was cut by the Knicks, therefore they had to pay for his entire salary.

        And yes, sure players made $15 mil per season in 2001, doesn’t make those contracts OK. Houston was broken down by midway through his contract.

        And teams can only re-sign their own free agents and go over the cap if they own their Bird Rights, but still have to pay the luxury tax. So it’s not like they can just throw whatever money they want at people with no consequences.

  4. Wasn’t* standard practice.

  5. I get what you are saying, it is pretty tough to compare different eras like this as we aren’t comparing apples to apples in terms of pay scales. Add in the fact that there are so many awful contracts every year and this becomes an even tougher task. You did find some hidden gems in this list though… I wonder how much of the $100m contract AH got paid considering how he retired before finishing it out? If he got it paid in full than he and his agent are effing studs lol

    It is your article and I don’t want to come off as a dbag as I did enjoy it, but it would be awesome to add some other notable players from that era and their contracts for comparison, to size up just how awful some of these contracts really were. It really was a solid list though, better than I could come up with. Cheers Ryan and I look forward to your future articles

    • Since Houston’s retirement is due to a basketball related injury, he got every penny. I believe the NFL is the only sport where the contracts are not guaranteed. (Not sure about the NHL.) The only time it would not be guaranteed is if he injured himself doing something that he was not supposed to be doing. Lots of athletes contracts forbid just about anything that could injured a player…like riding ATVs in the off-season, etc.

      However, the Knicks would not have had to pay it all themselves. Insurance would have paid for any part of the contract that came after the retirement. (They were still on the hook for the full amount salary cap-wise though.)

      • It depends on whether or not they had any injury insurance in his contract. It’s not always standard practice to do so. I would bet they did have some insurance.

  6. Obviously when you write something like this you expect there to be disagreements and discussion. It’s all opinion so I totally welcome the debate. As for Houston I’m fairly certain he got the full $100 mil.

  7. great list — first post I’ve ever made on yardbarker that isn’t lambasting the writer (frequently)

  8. lakawak says:

    Go figure…Isiah Thomas was responsible for 3 of these.

  9. Peja was great with the Kings, we should never have let him go he was scoring 20 points with us and won the three points contest a couple times

  10. Isaiah wasn’t a Knick yet in 2001… That was the Scott Layden regime, which frequently appeared to be little more than a puppet show for the Dolans…

    So where’s Grant Hill’s deal with the Magic (roughly the NBA equivalent of Carl Pavano)… ? I mean, obviously, they were supposed to know he would underperform, since, by your logic, the Knicks knew Houston would underperform and yet still threw big money at him anyway…

    • Isiah Thomas was responsible for the Austin Croshere deal in Indiana. And before you say that he was just the coach then, well, don’t be naïve. He called the shots.

    • Plus…yes, they SHOULD have known that a 30 year old is wayyyyy too old to be giving 6 year deals to, unless they are front ended and the latter years are for very little money. It s VERY rare for someone to perform at that level at age 36. This is not baseball where a lefty reliever or DH can hang on to age 40, or the NFL where a punter can go straight from receiving a paycheck to getting social security.

      that is why more teams will NOT sign a player to a huge deal beyond age 34 or so.

      • NBA players don’t ever do front-loaded contracts. The NBAPA frowns on such things and players agree.

        • This is just a question, not an argument…

          Front loaded contracts are not done in the NBA…but backloaded is pretty normal right? I only ask cuz of Lin and Asik’s current contracts in Houston.

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