The 25 Worst Contracts in NBA History

Image via Complex Original

Year: 2004
Contract: 6 years, $42 million

Ten years ago, the NBA was in a really bad place. Everyone was signining big contracts. Adonal Foyle, a very average backup center was able to finagle $42 million from the Golden State Warriors despite never averaging more than 5.9 PPG and 7.0 RPG. Foyle continued his subpar career averaging 4.0 PPG and 4.8 RPG while only playing three years of his six-year deal with Golden State before being waived.

Year: 1996
Contract: 7 years, $101 million

Juwan Howard was a good player, but got paid like a great player. He picked the right time to peak during his second year when he made his lone All-Star team. Howard averaged 22.1 PPG, 8.2 RPG, and 4.4 APG during that season, but everyone forgets that Howard got ample playing time as well as shot attempts because fellow Bullets star Chris Webber dealt with a separated shoulder, playing in only 15 games that season. Howard almost signed with the Heat in '96, but after the acquisition was rescinded, he became the first $100 million man in NBA history. Juwan never played at the same level as that previous season and the Bullets Wizards traded him in '01.

Year: 2005
Contract: 5 years, $70 million

The worst free agent acquisitions are usually the consolation prizes. After striking out on free agents Ray Allen and Michael Redd, the Cavaliers decided to go with their third option which was guard Larry Hughes. Hughes was coming off a strong season with Washington, but this was a pure reach by Cleveland. Hughes dealt with injury problems, and his mediocre jump shot hurt the Cavs as they needed to make space for centerpiece LeBron James. Questionable front office moves like this is why King James is in South Beach.

Year: 2003
Contract: 7 years, $126 million

During the early years of Jermaine O'Neal's contract extension with the Pacers, it seemed to make sense. In the first season, O'Neal finished third in MVP voting behind Kevin Garnett and Tim Duncan, he led the Pacers to a 61-21 record, and was one of four players to average 20 PPG and 10 RPG during the 2003-04 season; it all went downhill for Indiana.

The Malice at the Palace brawl left Jermaine and teammates Ron Artest and Stephen Jackson suspended for a number of games and took Indiana from an early season champion favorite to an average playoff team. After numerous years on the decline, O'Neal missed 84 games from '05-'08 before being traded to the Raptors. O'Neal's contract could be a great example of the change in CBA negotiations that altered the amount of years allowed for free agents to receive in their contract.

Year: 2006
Contract: 5 years, $64 million

Peja Stojakovic is known throughout NBA history as one of the best and most effective shooters of all time. When he signed with the New Orleans Hornets, everyone expected a happy marriage, but injuries and ineffectiveness led to Stojakovic falling off in New Orleans after some solid play at the beginning of the contract. At least he got that ring with the Dallas Mavericks before ending his career.

Year: 2008
Contract: 5 years, $80 million

This contract signing by Elton Brand turned out to be a major disaster. Brand's signing with the Philadelphia 76ers was a part of the '08 triangle of terror. Baron Davis signed with the Clippers expecting Brand to re-sign with the Clippers, but Elton spurned Los Angeles and moved on to Philadelphia. In response to the Warriors losing Davis, they signed Corey Maggette away from the Clippers. All of these transactions were pretty awful and left all three teams mediocre for years after making such bad high-priced acquisitions.

Year: 2004
Contract: 7 years, $92 million

It was a sad day in New Jersey when Kenyon Martin left the Nets and went to the Denver Nuggets in a sign-and-trade. Martin signed for an astronomical seven years, and $92 million with Denver, but knee injuries absolutely derailed his career. He had microfracture surgeries on both knees and missed 118 games in his first four seasons in Denver. He failed to live up to the hype as many people thought that the pairing of Martin with a Nuggets frontline that already featured Carmelo Anthony, Marcus Camby, and Nene would be one of the best in the NBA.

Year: 2000
Contract: 7 years, $86 million

Brian Grant was always one of the more solid forwards in the NBA. He was a workhorse as a defender and strong rebounder for the Trail Blazers during the early part of his career. After signing with Miami in a sign-and-trade, Grant joined Miami and while relatively productive, he was never able to live up to the humongous contract he signed as Miami went from solid Eastern Conference playoff team into a rebuilding process.

He did help the Heat to a championship indirectly when he was dealt along with Caron Butler and Lamar Odom to the Lakers for Shaquille O'Neal. The Heat probably wouldn't have been able to make that deal happen without Grant's enormous contract, so the Heat owe Grant a ring. JK!

Year: 2006
Contract: 4 years, $60 million

Joe Dumars has made some bad free agent decisions over the past few years, but one of his greatest decisions was the one he didn't make. Dumars chose not to re-sign Ben Wallace after the Chicago Bulls offered Big Ben an awfully large deal. Short story, Wallace was on the decline which is disappointing, but not shocking. He was a player who relied on his athleticism, so once his that faded, the Bulls traded him just one and a half seasons after he signed the deal.

Year: 1998
Contract: 6 years, $86 million

Jayson Williams was a quality big man in the NBA for about four seasons. During those years, he grabbed 12 boards a game and made an All-Star team with the New Jersey Nets in '98. Williams broke his leg in a collision with Stephon Marbury and 30 games into his contract he had career ending surgery. You know the rest of the story.

Year: 2000
Contract: 7 years, $86 million

Vin Baker was ultimately deserving of his contract for the Seattle Superonics when he got it. He was a gold medalist and a four-time All-Star, who had experienced a couple of down years prior to the contract but nothing alarming. Unfortunately, he was unable to live up to those high expectations after signing his contract. Baker's play consistently dropped for three consecutive seasons amid injuries and weight issues. Baker was then traded to Boston in 2002, where his struggles with alcoholism were revealed.

Year: 2007
Contract: 6 years, $118 million

Rashard Lewis was a nice player, but not a great player. Lewis had made just one All-Star team in his NBA career, but In May of 2007, he opted out of his deal with the Sonics and somehow convinced the Magic to a sign-and-trade maximum contract. Now Lewis was ridiculously overpaid, but he was valuable to the Magic making one All-Star team in Orlando and solid contributions to a Magic team that made the '09 NBA Finals. Lewis' value to the team was worth a sizable salary, but not as bad as some of these players who contributed very little for tons of money.

Year: 1997
Contract: 6 years, $65 million

Don't put all of your eggs in one basket. Bryant "Big Country" Reeves was the first ever draft pick of the Vancouver Grizzlies franchise, and had a decent start to his career with solid individual performances in his first few years. Unfortunately, Reeves had arthroscopic surgery on his knee in '99, and faced more problems with chronic back problems that forced him to retire early in '02. The Grizzlies were left to foot the bill of a player who really gave them two-and-a-half seasons of basketball for a six-year deal.

Year: 2002
Contract: 7 years, $70 million

Raef LaFrentz was a solid big man. He blocked shots and also could step out the three-point line and make plays off the dribble or as a catch and shoot player. The problem was the injuries and the ineffectiveness of LaFrentz. He was a good player, but sometimes teams forget how long of a commitment seven years is. Somehow the Mavericks were able to offload his contract in 2003 in a trade to the Boston Celtics that sent Antoine Walker to Dallas.

Year: 1999
Contract: 7 years, $87 million

Everyone always talks about the contributions Penny Hardaway brought to the NBA as a phenomenal player from 1993-97. He was dominant, but some red flags popped up with several knee injuries and also some issues with coaches towards the end of his tenure in Orlando. Phoenix was willing to take a flyer on Penny offering him the max, but after one strong season in Phoenix with Jason Kidd as "Backcourt 2000," Hardaway dealt with microfracture surgery and missed nearly the entire 2000-01 season. He came back but was never the same player again.

Year: 2004
Contract: 7 years, $73 million

This signing will go on forever as a terrible Mavericks signing because Erick Dampier is Erick Dampier. On the low, people will never remember that Isiah Thomas was trying to acquire Dampier before the Mavericks swooped in and acquired him. That would be attrocious for the Knicks, but there would probably never be an Eddy Curry or Jerome James sighting in New York. Know this as the Damp that saved Isiah.

Year: 2005
Contract: 5 years, $30 million

Isiah Thomas had a problem. He had an obsession with the mid-level exception when he was managing the Knicks roster. Outside of the abomination of a signing of Jerome James, Thomas also struck out with Jared Jeffries while using the full mid-level exception ($5.765 million). Getting back to James, he was out of shape and considered a major bust for the Knicks. Knicks fans will probably not enjoy reading anything that reminds them of Jerome on the court, so enjoy Jerome talking about spaghetti.

Year: 1996
Contract: 7 years, $33 million

Thirty-three million over seven years in an NBA contract is nothing to get worried over with salaries like the ones today. Back in the '90s this was an obscene amount of money. McIlvaine was making more money than stars like Shawn Kemp, Karl Malone, Scottie Pippen and Mitch Richmond despite being a player who never averaged 2.3 points and 2.9 rebounds before signing with the Sonics. McIlvaine's signing infuriated Shawn Kemp eventually leading to his departure and the quick end to a dynasty in Seattle.

Year: 2005
Contract: 6 years, $56 million

Eddy Curry was young and was an offensive force which interested the New York Knicks and Isiah Thomas greatly. Curry was solid offensively, but was known for a lack of rebounding and defensive prowess. On top of that, Curry was dealing with heart issues that had affected him and the Knicks and Isiah were still willing to take the risk of a sign-and-trade for Curry despite having a large heart and irregular heartbeat. Curry played a 10 total games for the Knicks from 2008-2010, but was still able to make $19 million.

Year: 2003
Contract: 4 years, $76 million

New York fans rejoiced after the Knicks acquired hometown hero Stephon Marbury, but he quickly became a villain in New York as the Knicks made the playoffs once (swept in first round of '04) throughout his tenure in New York. It was a disappointing stretch that saw Marbury cause more harm than good. That harm includes the Anucha Brown Saunders scandal as well as fights with coaches Larry Brown and Mike D'Antoni.

Year: 2001
Contract: 6 years, $100 million

There was one point where every Knicks fan like and supported Allan Houston. The Knicks' offensive star had one of the biggest shots in Knick history with his Game-Winner in Game 5 of the first round that upset the top seeded Heat and led New York on a Cinderella run to the 1999 NBA Finals. Houston was great until he signed that six-year, $100 million contract that changed all expectations for him. He was still solid, but his performance and the Knicks bare cupboard of a roster led to Knicks fans pointing to his extension as the downfall of the team.

Year: 2008
Contract: 6 years, $111 million

One thing Gilbert Arenas is, is honest. Just last month, he admitted that he might've signed the worst contract in NBA history. It was a pretty terrible experience for all parties involved. After re-upping with Washington, Arenas dealt with injuries and also an infamous incident in which he brought firearms into an NBA arena. After that, the Wizards eventually got rid of Arenas in a trade to the Magic for another bad contract in Rashard Lewis. We will forever miss Hibachi.