Ranking the Worst Contracts in NBA Free-Agency History

Kerry Miller@@kerrancejamesCollege Basketball National AnalystJuly 2, 2018

Ranking the Worst Contracts in NBA Free-Agency History

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    Chandler Parsons
    Chandler ParsonsBrandon Dill/Associated Press

    NBA teams handed out a lot of atrocious contracts during the 2016 free-agency period, but the four-year, $94 million deal the Memphis Grizzlies gave to Chandler Parsons is already looking like one of the worst signings ever.

    However, that contract isn't quite as brutal as what Isiah Thomas did to the New York Knicks in 2005 and 2006. In fact, Knicks fans would be advised to consume quite a few antacids before proceeding, as that franchise is responsible for three of the top five spots on this list of the worst contracts in NBA free-agency history.

    Ranking for this list is primarily based on (lack of) return on investment. Most of these players were paid like All-Stars, but they produced like benchwarmers—often due to injury. This negatively impacted the team's ability to competeboth on the floor and in subsequent free-agency bidding wars.

Players Who Re-Signed with Same Team

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    Gilbert Arenas
    Gilbert ArenasLuis Alvarez/Associated Press

    Only players who changed teams during free agency were eligible for a spot in the top 10. However, we would be remiss if we didn't point out a handful of guys who turned out to be anything but a hometown discount.

            

    Jon Koncak, Atlanta Hawks: six years, $13.1 million (1989)

    Jon "Contract" Koncak looks like a bargain by today's standards, but back in 1989, this deal was ludicrous for a part-time starter. To put it in context, over the course of the six seasons of Koncak's contract, Magic Johnson made $11.9 million. But while Johnson had 138 triple-doubles in his career, Koncak had all of four double-doubles in these six years.

          

    Juwan Howard, Washington Bullets: seven years, $105 million (1996)

    This was the year NBA contracts went bonkers. Shaquille O'Neal, Alonzo Mourning and Howard all signed seven-year deals worth at least $105 million. But while Mourning was an All-Star in four of those seven seasons and O'Neal became one of the greatest of all time, Howard's career peaked the year before the Bullets/Wizards inked him long-term. He was an All-Star at 23 years of age in 1996, but never again.

          

    Jayson Williams, New Jersey Nets: six years, $86 million (1998)

    After a slow start to his career, Williams blossomed into a double-double machine in 1997 and 1998, leading the Nets to invest heavily in the 30-year-old. Little did they know they were investing in just 30 more games, as that's how long Williams lasted into this contract before suffering a career-ending broken leg.

           

    Vin Baker, Seattle SuperSonics: seven years, $86 million (1999)

    Baker was a four-time All-Star who played in almost every game from 1994 to 1998, averaging 19.7 points and 9.6 rebounds per game. Seattle jumped at the chance to lock up the successful 27-year-old for as long as possible. However, he was one of many players who let himself go during/after the strike-shortened 1998-99 season, and he was never the same.

           

    Allan Houston, New York Knicks: six years, $100 million (2001)

    People always point to this contract as one of the worst ever, but Houston gave the Knicks a great return on investment for the first 2.7 years of this six-year extension, averaging better than 20 points per game. A knee injury ended his career in 2005, but he was still on New York's payroll for the next two seasons. It's largely because of Houston's contract that the NBA introduced the amnesty clause.

           

    Darius Miles, Portland Trail Blazers: six years, $48 million (2004)

    Miles bounced from the Clippers to the Cavaliers to the Trail Blazers before turning 23. The high school phenom never quite tapped into his immense potential, but Portland made a big bet that he would get there eventually. A devastating knee injury ensured that would never happen.

             

    Gilbert Arenas, Washington Wizards: six years, $111 million (2008)

    From 2004 to 2007, Arenas averaged 27.7 points per game and was an All-Star in all three seasons. After an injury-plagued 2007-08, he opted out of the final year of his contract with the Wizards, forcing them to shell out the big bucks to keep him in town. They did, but injuries and an infamous firearms incident limited him to 55 games in two-plus seasons with Washington before it traded him to Orlando for the remainder of Rashard Lewis's equally brutal contract.

           

    Brandon Roy, Portland Trail Blazers: five years, $82 million (2009)

    Portland already knew about Roy's knee problems when it signed him to this big extension, but his health deteriorated faster than anyone was expecting. He retired one year into the deal. To make matters even worse for the Trail Blazers, he came back for five games with the Minnesota Timberwolves in 2012-13, which reportedly cost Portland $17 million.

           

    Chris Bosh, Miami Heat: five years, $118 million (2014)

    While most of the decisions on this list were questionable from the moment the ink hit paper, this one made perfect sense at the time. Along with LeBron James and Dwyane Wade, Bosh helped carry the Heat to the NBA Finals in four consecutive years. Unfortunately, blood clots resulted in his playing just 97 games after signing this $118 million deal.

Honorable Mentions

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    Erick Dampier
    Erick DampierMatt York/Associated Press

    Bobby Simmons, Milwaukee Bucks: five years, $47 million (2005)

    Simmons looked great in 2004-05 alongside Corey Maggette and Elton Brand, averaging 16.4 points per game as the third wheel of a Clippers team that was going nowhere fast. But that suddenly successful season convinced Milwaukee to pony up the big bucks when Simmons hit free agency. His first season wasn't too shabby, but he missed the entire 2006-07 season with an ankle injury and never looked anything close to the same afterward.

               

    Grant Hill, Orlando Magic: seven years, $93 million (2000)

    As far as the injury bug is concerned, there might not be a bigger "What if?" in all of sports than Grant Hill. He averaged 21.6 points, 7.9 rebounds and 6.3 assists per game in his first six seasons in the NBA (all with Detroit) and was well on his way to becoming one of the all-time greats, but he could not stay healthy in Orlando. He did average better than 16 points per game for the 200 games he was able to play in Orlando, though, so it's hard to justify this as one of the 10 worst free-agency investments ever.

             

    Erick Dampier, Dallas Mavericks: seven years, $73 million (2004)

    This one always resurfaces when people mention the NBA's worst contracts, but Dampier started 356 games and was a serviceable defender and rebounder in his six seasons with the Mavericks. That's way better than most of the albatrosses that lie ahead. However, the real reason this signing is recalled with such disdain is probably because this was the same summer Dallas tried to pinch pennies in its negotiations with Steve Nash and ended up losing him to the Sunsright before he became a two-time league MVP.

                   

    Larry Hughes, Cleveland Cavaliers: five years, $70 million (2005)

    Talk about performing well in a contract season. The year before getting this deal with the Cavs, Hughes averaged 22.0 points, 6.3 rebounds, 4.7 assists and 2.9 steals with the Wizards—all career highs. He was OK for Cleveland for a few seasons, which keeps him from landing in our top 10, but he was never anything close to becoming LeBron James' Scottie Pippen.

                    

    Eddie Robinson, Chicago Bulls: five years, $32 million (2001)

    There are a lot of forgettable names on this list, but I honestly have no recollection of this one. Evidently, the undrafted forward who started 14 games in his first two seasons with the Charlotte Hornets was worth a $32 million flyer to the Bulls. He averaged just 11.5 points and 4.5 rebounds per 36 minutes over the next two-plus seasons before playing his final NBA game at the age of 27.

            

    Evan Turner, Portland Trail Blazers: four years, $70 million (2016)
    Ian Mahinmi, Washington Wizards: four years, $64 million (2016)

    Because of a spike in the salary cap (and floor) and an expected growth in those areas for years to come, there were some atrocious contracts handed out in the summer of 2016. Several of them rank in our top 10, and it was tempting to include these two as well. However, Turner and Mahinmi have been about as good as advertised. It's just that two summers ago, $17 million per year was the going rate for mediocre starters/respectable reserves.

10. Jim McIlvaine: 7 Years, $34 Million

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    Brian Bahr/Getty Images

    The Contract: Seven years, $33.6 million with Seattle SuperSonics, signed in 1996

    Contract Year (with Washington): 2.3 PPG, 2.9 RPG, 2.1 BPG

    Tenure with New Team: 3.5 PPG, 3.7 RPG, 1.9 BPG

    As previously mentioned, 1996 was the year the NBA really started throwing big contracts around. Shaquille O'Neal, Alonzo Mourning and Juwan Howard all got seven-year, seven-figure deals, and Seattle followed suit by agreeing to a seven-year deal with Jim McIlvaine.

    Wait, who?

    To that point in his brief career, McIlvaine had started only six games with the hapless Bullets. The 1994 second-round pick from Marquette had scored 10 or more points in a game just twice in the NBA and had yet to record a double-double.

    Evidently, though, this was enough evidence for the Sonics to give McIlvaine a deal that paid him more in 1996-97 than Sam Perkins and Hersey Hawkins and almost as much as Shawn Kemp and Detlef Schrempf, per Eskimo.com. Kemp infamously became furious with the franchise and forced a trade to Cleveland the following year.

    As you can see above, McIlvaine didn't provide much return on that investment. He was the starting center for 151 of Seattle's games in the two seasons before it traded him to New Jersey, but he only had one double-double to show for all that playing time.

9. Elton Brand: 5 Years, $80 Million

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    Matt Slocum/Associated Press

    The Contract: Five years, $79.8 million with Philadelphia 76ers, signed in 2008

    Contract Year (eight games with Los Angeles Clippers): 17.6 PPG, 8.0 RPG, 1.9 BPG

    Tenure with New Team: 13.3 PPG, 7.4 RPG, 1.3 BPG

    For the first eight seasons of his career, Elton Brand was one of the best power forwards in the league. He consistently had a player efficiency rating north of 20 while averaging 20.3 points, 10.2 rebounds, 2.7 assists and 2.1 blocks per game. In his lone trip to the postseason during his prime, he put up 25.4 points in the 2006 playoffs.

    Even though Brand missed almost the entire 2007-08 season after rupturing an Achilles tendon, Philadelphia invested big in the hope that he could regain his pre-injury form.

    He didn't.

    By no means was Brand terrible with the 76ers. But between the recovery from the Achilles and the shoulder injury he suffered a few games into this big contract, he was only able to give his new team about 70 percent of what he gave Chicago and Los Angeleswhich Philadelphia could have gotten elsewhere for a lot cheaper than $16 million per year.

8. Timofey Mozgov and Luol Deng: 4 Years, $136 Million (combined)

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    Timofey Mozgov
    Timofey MozgovTony Dejak/Associated Press

    The Contract (Timofey Mozgov): Four years, $64 million with Los Angeles Lakers, signed in 2016
    Contract Year (with Cleveland): 6.3 PPG, 4.4 RPG
    Tenure with New Team: 7.4 PPG, 4.9 RPG

    The Contract (Luol Deng): Four years, $72 million with Los Angeles Lakers, signed in 2016
    Contract Year (with Miami): 12.3 PPG, 6.0 RPG, 1.9 APG
    Tenure with New Team: 7.5 PPG, 5.2 RPG, 1.3 APG

    The 2016 spike in the salary capfrom $70 million to $94.14 millioncame at a horrendous time for the Los Angeles Lakers. With Kobe Bryant's massive contract coming off the books after his retirement, they had no choice but to spend recklessly in free agency just to reach the salary floor. Worse yet, they had to do so in a summer when every other team suddenly had more cash to throw around.

    Thus, Mozgov and Deng got paid like royalty for no good reason.

    Mozgov made slightly less than $5 million in 2015-16, and he didn't even play well. In fact, after averaging 9.5 points and 6.9 rebounds per game in the previous two seasons, he plummeted more than 30 percent in each of those categories. And yet, his salary more than tripled to $16 million that offseason because the money had to go somewhere. He played just 54 games in his one season with the Lakers.

    And then there's Deng, who the Lakers are paying $18 million per year just to work out with the team. Even though he's healthy, he has appeared in just one of the last 104 games the Lakers have played, as they have chosen to put as many minutes as possible toward developing the younger guys while rebuilding through the draft.

    Given that goal, you could argue these two contracts weren't bad at all. It maintained the illusion of trying to build a contender without actually doing so, and it put the team in perfect position to spend big this year instead. But as far as short-term return on investment is concerned, the Lakers shelled out a lot of Benjamins for minimal production.

7. Anfernee "Penny" Hardaway: 7 Years, $87 Million

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    MATT YORK/Associated Press

    The Contract: Seven years, $86.7 million with Phoenix Suns, signed in 1999

    Contract Year (with Orlando): 15.8 PPG, 5.7 RPG, 5.3 APG, 2.2 SPG

    Tenure with New Team: 12.4 PPG, 4.5 RPG, 4.2 APG, 1.3 SPG

    Penny Hardaway is right up there with Grant Hill on the NBA's list of guys who might've been all-time greats if they could have stayed healthy. But the reason we're placing Hardaway in the top 10 while not including Hill is because Penny's injury concerns were apparent long before Phoenix made its hefty investment in the point guard.

    Hardaway was unbelievable in college with Memphis, and he carried that momentum into three great seasons in the NBA alongside Shaquille O'Neal with Orlando. He averaged 19.5 points, 7.0 assists and 4.7 rebounds and missed just five games in those first three years.

    Over the course of the next five years, though, he missed almost as many games (186) as he played (192), primarily due to an awful left knee injury suffered in 1997. Unfortunately for Phoenix, his healthiest season during that five-year stretch came in the lockout-shortened 1998-99 campaign, when Hardaway appeared in all 50 games before hitting free agency.

    But it was fool's gold.

    His first season with the Suns was solid, as he averaged 16.9 points and 5.3 assists in 60 regular-season games, along with 20.3 points and 5.7 assists in nine postseason games. After two microfracture surgeries on his left knee in 2000, though, he was never anything close to the same. It wasn't until after the Suns unloaded him on the Knicks in 2004—and signed his replacement, Steve Nash, that offseasonthat they became relevant again.

6. Ben Wallace: 4 Years, $60 Million

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    Jerry Lai/Associated Press

    The Contract: Four years, $60 million with Chicago Bulls, signed in 2006

    Contract Year (with Detroit): 7.3 PPG, 11.3 RPG, 2.2 BPG

    Tenure with New Team: 5.9 PPG, 9.9 RPG, 1.9 BPG

    It was inevitable that someone was going to fork over a ton of dough for Ben Wallace. It's just unfortunate for the Bulls that they won the bidding war.

    Though he was never much of a scorer, Wallace was an insatiable (and injury-free) defender and rebounder during his first six seasons with Detroit. In 2001-02, he led the NBA in both rebounds (13.0) and blocks (3.5), and he was an All-Star in each of the four seasons before reaching free agency in 2006. Chicago chose to believe the 32-year-old still had a few good seasons left in the tank.

    But he started wearing down in a hurry.

    In his first season with Chicago, Wallace's per-game averages in points, rebounds and blocks were all worse than each of his previous five years in Detroit. Things only got worse from there, as his numbers dropped about another 20 percent across the board in year No. 2. He didn't even make it two full seasons before the Bulls traded him.

    Perhaps the biggest reason Chicago regretted this pickup is that it already had a cheaper and younger version of Wallace on the roster. But instead of sticking with Tyson Chandlerwho the Bulls signed to a six-year, $64 million deal the previous summerthey traded him away for pennies on the dollar to make this Wallace move possible. Chandler blossomed after leaving Chicago and averaged 9.9 points and 10.3 rebounds per game over the course of the next nine seasons.

5. Amar'e Stoudemire: 5 Years, $99.7 Million

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    Phelan M. Ebenhack/Associated Press

    The Contract: Five years, $99.7 million with New York Knicks, signed in 2010

    Contract Year (with Phoenix): 23.1 PPG, 8.9 RPG

    Tenure with New Team: 17.3 PPG, 6.7 RPG

    One year into the Amar'e Stoudemire signing, it looked like the Knicks were going to get their money's worth and then some. He averaged 25.3 points, 8.2 rebounds and 1.9 blocks in 78 games played for a team that finished above .500 for the first time in a decade. The 28-year-old was named an All-Star for the sixth time in his career and was voted All-NBA (second team) for the fifth time.

    And then the bottom dropped out.

    Stoudemire dealt with poor conditioning, the death of his brother and a bulging disk in his back during the lockout-abridged 2011-12 season. After four straight years of averaging at least 21.4 points per game, that combination of factors resulted in a plummet to 17.5 points.

    Knee injuries and a reduction in playing time led to another drop to 14.2 points per game (in just 29 games played) the following year. The downward spiral continued yet again as he averaged 11.9 points and 4.9 rebounds in 2013-14. That's downright dreadful production from what was the third-highest-paid player in the NBA that year.

    Midway through the fourth season of his five-year deal, the Knicks gave up and bought out the remainder of Stoudemire's mammoth contract.

4. Joakim Noah: 4 Years, $72 Million

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    Kamil Krzaczynski/Associated Press

    The Contract: Four years, $72.6 million with New York Knicks, signed in 2016

    Contract Year (with Chicago): 4.3 PPG, 8.8 RPG, 3.8 APG

    Tenure with New Team: 4.6 PPG, 7.9 RPG, 2.0 APG

    Most of these were potentially good signings that went terribly wrong, but what exactly did the Knicks expect when they committed to four years of paying Joakim Noah a salary on par with that of John Wall and DeMarcus Cousins?

    At his peak, Noah was a high-value hustle guy. From 2009 to 2014, he averaged 11.5 points, 10.8 rebounds and 3.4 assists per game. He was an All-Star in both 2013 and 2014 and was a foundation piece for a Bulls team that was perennially in the playoffs.

    Had the Knicks signed Noah to this deal in the 2014 offseason, no one would have blamed them. Heck, it may have been praised as one of the best pickups of that summer.

    But it was beyond irresponsible to give him this contract after watching him physically deteriorate in 2015 and 2016. Noah's production dropped off a cliff and he lost his starting job long before the series of shoulder injuries that limited him to 29 games in the season before hitting free agency.

    Evidently, though, the Knicks thought he could rediscover his prime form in his 30s. Instead, he has been battling shoulder and knee injuries that limited him to 40 minutes played in the entire 2017-18 season.

    It would take one heck of a miracle in the next two years for Noah to live up to his contract. More likely, this could be remembered for years to come as the worst individual contract ever.

3. Rashard Lewis: 6 Years, $118 Million

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    Phelan M. Ebenhack/Associated Press

    The Contract: Six years, $118.2 million with Orlando Magic, signed in 2007

    Contract Year (with Seattle): 22.4 PPG, 6.6 RPG, 2.4 APG

    Tenure with New Team: 16.3 PPG, 5.1 RPG, 2.1 APG

    The most stupefying part of Rashard Lewis' six-year deal worth almost $20 million per season is that he was never that good. Teams eventually regretted their big deals with the likes of Elton Brand, Ben Wallace and Amar'e Stoudemire, but it's hard to fault them for investing in All-NBA guys who were clearly among the best in the league.

    Lewis, on the other hand, was a volume scorer who went to one All-Star Game in his nine seasons with Seattle. He was never named to an All-NBA team. He never led the league in anything. He had an above-average efficiency rating, but nothing to suggest he deserved to be one of the highest-paid players in the league.

    Even worse for Orlando, Lewis immediately started to decline upon arrival. After three straight years of averaging better than 20 points per game with the SuperSonics, Lewis went from 18.2 to 17.7, 14.1 and 12.2 before the Magic were finally able to ship him to Washington.

    But wait.

    There's more.

    Lewis's contract was backloaded, meaning he got more expensive while becoming less valuable. Per Eskimo.com, Lewis made $14.88 million in his first year in Orlando. That salary increased to $16.45 million in his second year, $18.87 million in year No. 3, $19.57 million in the fourth year and $21.14 million in the fifth. In the 2010-11 season, only Kobe Bryant was paid a higher salary than Lewis, which is nothing short of preposterous.

2. Chandler Parsons: 4 Years, $94 Million

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    Matt Slocum/Associated Press

    The Contract: Four years, $94.5 million with Memphis Grizzlies, signed in 2016

    Contract Year (with Dallas): 13.7 PPG, 4.7 RPG, 2.8 APG

    Tenure with New Team: 7.1 PPG, 2.5 RPG, 1.8 APG

    Chandlers Parsons' contract is the Mona Lisa of the terrible deals that were handed out in the summer of 2016.

    Parsons has never been an All-Star. As far as player efficiency rating is concerned, he was a marginally above-average player in each of the four seasons before hitting free agency. But he also missed the end of both the 2015 and 2016 seasons due to knee surgeries, so there were injury concerns on top of his play that wasn't improving.

    In any other year, owners would have been cautious in their pursuit of this free agent. But in the summer of spending like there's no tomorrow, the Grizzlies made Parsons the 15th-highest-paid player in the league for the 2016-17 season. Better yet, they committed to increasing that salary by roughly $1 million per year over the subsequent three years.

    Even if he replicated what he had done for the previous four years, it would've been a bad contract. Giving a guy Anthony Davis money for Jae Crowder production doesn't make sense. But at least it would've been better than what Memphis actually received.

    Thanks in large part to continued knee issues, Parsons has appeared in just 70 games over the last two seasons, playing well below average in both years. He has two years left to try to turn things around, but is that a half-empty or half-full glass?

1. The Increasingly Poor Decisions of Isiah Thomas

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    Eddy Curry
    Eddy CurryJULIE JACOBSON/Associated Press

    The Contract (Eddy Curry): Six years, $60 million with New York Knicks, signed in 2005
    Contract Year (with Chicago): 16.1 PPG, 5.4 RPG
    Tenure with New Team: 15.2 PPG, 5.8 RPG

    The Contract (Jared Jeffries): Five years, $30 million with New York Knicks, signed in 2006
    Contract Year (with Washington): 6.4 PPG, 4.9 RPG, 1.9 APG
    Tenure with New Team: 4.3 PG, 3.9 RPG, 1.2 APG

    The Contract (Jerome James): Five years, $30 million with New York Knicks, signed in 2005
    Contract Year (with Seattle): 4.9 PPG, 3.0 RPG, 1.4 BPG
    Tenure with New Team: 2.5 PPG, 1.8 RPG, 0.4 BPG

    Isiah Thomas' tenure with the New York Knicks was like watching a slow-motion train wreck. He traded away draft picks about as often as he possibly could, and he made a nasty habit of giving mid-level exceptions to free agents who were never going to be focal pieces for a winning team.

    The deal to get Curry was a combination of both poisonous practices, as Thomas gave away four (!!!) draft picks in a sign-and-trade for "Baby Shaq." To be fair, Curry was solid for his first two-plus seasons in New York. He started 81 games and led the team in scoring in 2006-07. But his conditioning deteriorated to the point where he only appeared in 10 games in his final three seasons with the Knicks.

    In James and Jeffries, Thomas committed about 20 percent of the team's salary cap for half a decade to two lottery tickets that didn't pan out.

    In Thomas' defense, James started 80 games at center for a 52-win Seattle team in 2004-05, and Jeffries started 77 games at power forward for a 42-win Washington team in 2005-06. In theory, those two guys and Curry should have given New York a serviceable frontcourt rotation around which guards Stephon Marbury, Steve Francis and Jamal Crawford would become the stars.

    Instead, James was unplayable from day one in New York, and Jeffries was never anything more than a minutes eater, posting a sub-10 PER in each of his four years with the Knicks.

    If it had just been one of these terrible deals, New York might have been fine. But because all three salary-cap nightmares happened concurrently, it turned the Knicks into a laughingstock. And because Thomas had given away so many draft picks, they rarely even had the luxury of tanking for a better spot in the lottery.

                      

    Kerry Miller is a multisport writer for Bleacher Report. You can follow him on Twitter, @kerrancejames.