Throughout the course of the history of free agency in the NBA, there have been multiple franchise-altering deals that have taken place (like Shaquille O’Neal going to Los Angeles and LeBron James going to Miami). But for every one of those, you can probably find a half-dozen (or more) contracts that altered the course of an NBA team in the exact opposite direction — crippling the team’s salary cap and overall financial flexibility, setting them back for a multitude of years.
Some of them look bad with the benefit of hindsight, and some of them came as NBA teams overpaid for certain positions or players, but many of them were seen as horrific deals from the moment they were signed. Here is our list of the worst contracts in recent NBA history.
Chris Webber: 15 years, $74.4 million (1993)
The rookie contract signed by Chris Webber, the #1 overall pick of the 1993 NBA Draft (he was selected by Orlando but subsequently traded to the Golden State Warriors in exchange for Anfernee “Penny” Hardaway and three first round picks) doesn’t get talked about enough.
Webber signed a $74.4 million contract spanning an absurd 15 years, but the most absurd part of it was the clause where Webber could opt out of the deal in Year 1. After clashing with former head coach Don Nelson, Webber exercised that opt out clause, forcing Golden State to trade the guy who was the rookie of the year and would become a five-time All-Star.
Jim McIlvaine: 7 years, $33.6 million (1996)
The old saying in the 1980’s and 1990’s was that if you were seven feet tall and could walk and chew gum at the same time, some NBA team was going to hand you a large contract. Just look at center Jim McIlvaine, who averaged less than 15 minutes per game with the Washington Bullets during his first two seasons in the NBA.
But when he became a free agent in 1996, the Seattle Supersonics signed him to a seven-year, $33.6 million free-agent contract. That deal effectively destroyed a really good Seattle team, as it led to acrimony between Shawn Kemp (who was jealous of McIlvane’s deal) and the Supersonics’ front office.
Shawn Kemp: 7 years, $107 million (1997)
As one of the great (if not underrated) stars of the late 1990’s, Shawn Kemp was extremely displeased with the Seattle Supersonics handing center Jim McIlvane a huge free agent contract, as opposed to taking care of the home-grown Kemp. Kemp demanded a trade, and was sent to the Cleveland Cavaliers prior to the 1997 season.
Cleveland game him the money he sought, in the form of a seven-year deal worth $107 million. But when the NBA lockout shortened the 1998-1999 NBA season, that’s when Kemp’s issues with substance abuse and weight gain began to destroy his once-spectacular NBA career.
Joe Smith: 1 year, $1.75 million (1998)
Joe Smith never really lived up to the hype of being the #1 overall pick in the 1995 NBA Draft. But Smith found a home in Minnesota, playing alongside superstar Kevin Garnett. But Smith’s contract extension in 1998 will go down as one of the worst in NBA history, not because of the amount, but because of the damage it caused to the franchise.
Smith and the Timberwolves agreed in an illicit deal where Smith signed a deal “below market value,” so the team could acquire some other players in the short term, with the promise of getting paid later. The league fined the Timberwolves franchise $3.5 million, but more severely, it took away five first-round picks. That destroyed the future of the team.
Bryant Reeves : 6 years, $61.8 million (1998)
— Bryant “Big Country” Reeves is another example of the horrible rookie contracts that teams used to hand out in the early 1990’s. Reeves played well early in his career, averaging just over 13 points per game in his first season and then just over 16 points per game in his second season.
But right after that, the then-Vancouver Grizzlies handed him a six-year, $61.8 million contract extension. Reeves battled injury and conditioning issues for the remainder of his career, and was out of the NBA before that new deal was finished.
Vin Baker: 7 years, $86 million (1999)
As if their decision to sign Jim McIlvane — and trade away Shawn Kemp — wasn’t bad enough, Seattle made another critical mistake, signing forward Vin Baker to a seven-year deal worth just under $87 million (after he previously arrived via the trade that sent Kemp to Cleveland).
After Baker arrived in Seattle, his once promising career began to decline rapidly, thanks to substance abuse issues off the court. While his tenure in Seattle was a disaster, things would only continue to get worse for Baker as his career progressed; at one point in time, he tipped the scales at over 300lbs.
Allan Houston: 6 years, $100.4 million (2001)
A deal that was such a horror show that the NBA came up with it’s own rule — in his namesake — to correct itself. In 2001, the New York Knicks signed Allan Houston to a six-year, $100.4 million contract extension. Coupled with subsequent injuries, his $20M+ salary per year made him the most toxic asset for any team to consider in the NBA.
In 2005, the NBA agreed on a new collective bargaining agreement (CBA), where the NBA effectively allowed one team to amnesty one contract from their salary cap ledger (although they’d still have to pay that player); that rule is commonly referred to as “the Allan Houston rule.”
Raef LaFrentz: 7 years, $70 million (2002)
A two-time All-American at the University of Kansas, Raef LaFrentz was the third overall pick by the Denver Nuggets in the 1998 NBA Draft. While LaFrentz did turn out to be an ok scorer in the NBA, including a career-high 14.9 points per game in 2001-2002, he wasn’t worth anywhere near the $70 million contract handed to him by the Dallas Mavericks in 2002.
As if that wasn’t bad enough, after becoming a huge free agent bust in Dallas, Portland signed LaFrentz later in his career to a $13 million contract, which didn’t fare any better.
Stephon Marbury: 4 years, $74 million (2003)
After Stephon Marbury had already worn out his welcome at two different NBA locales, the Phoenix Suns handed him a four-year, $74 million extension in 2003. In what shouldn’t be a surprise to anyone, the Suns ended up dumping him as well, trading him to the New York Knicks in 2004.
Having to foot the bill for the remainder of his deal, the Knicks paid Marbury approximately $88 million in his five years in Gotham, despite never winning a single playoff game.
Erick Dampier: 7 years, $70 million (2004)
A classic “looks like Tarzan but plays like Jane” guy, Shaquille O’Neal used to love making fun of Erick Dampier, often referring to him as “Erica Dampier.” In 2004, after averaging a career-high 12.3 points per game (and 12 rebounds per game), the Dallas Mavericks acquired Dampier via trade, and then signed him to a ghastly seven-year, $70 million contract.
For the rest of his time in Dallas, the Mavericks came to regret that deal. He averaged less than 10 points and nine rebounds per game throughout his time with the Mavericks.
Adonal Foyle: 6 years, $42 million (2004)
After being taken with the 8th overall pick in the 1997 NBA Draft, center Adonal Foyle averaged less than six points a game in each of his first seven seasons, and pulled down less than seven rebounds per game in six of those seven seasons.
Yet, the Golden State Warriors thought it’d still be a good idea to sign Foyle to a six-year, $42 million contract. Foyle’s stats then took another dip immediately after signing that deal, leading to the Warriors waving Foyle, even though he had three years and $29.2 million remaining on his contract.
Eddy Curry: 6 years, $60 million (2005)
At only 22 years old, center Eddy Curry — one of the building blocks for the Chicago Bulls in the post-Michael Jordan era — was hospitalized with an irregular heartbeat, and doctors wondered whether he had a congenital heart condition. Even after refusing to get tested for this, the New York Knicks not only acquired him via a trade, but then signed him to a $60 million contract over six years.
To say Curry’s tenure in New York was a disaster might be understating it. Between his health issues, constant battles with his weight, and numerous public incidents involving his immaturity, Curry is one of the biggest draft busts in NBA history.
Jerome James: 5 years, $30 million (2005)
In the summer of 2005, after a career spent bouncing around various teams and countries, forward Jerome James was a free agent who’d turn 30 years old when the following NBA season started.
But the New York Knicks once again threw caution to the wind when signing James, hanging him a 5-year, $30 million free-agent contract. He arrived into the subsequent training camp heavier and out of shape, and never played more than 45 games in a given season during his four years in New York.
Andray Blatche: 5 years, $35 million (2007)
It was dubious enough that the Washington Wizards handed a five-year, $15 million contract forward Andray Blatche, given that he averaged 3.2 points and 2.7 rebounds in 85 career games (spanning three seasons). But then, General Manager Ernie Grunfeld doubled-down on the bad deal, adding $28 million to Blatche’s deal, effectively making it a 5-year, $35 million deal.
There was absolutely no reason for Grunfeld to hand Blatche that type of money, considering the player was well-known for severe immaturity issues and a horrible work ethic. Unsurprisingly, Blatche was maddeningly inconsistent after signing said deal, but blamed everyone except himself for his shortcomings. Just two seasons later, Washington traded him away to the Brooklyn Nets.
Rashard Lewis: 6 years, $118 million (2007)
Rashard Lewis was one of the original “stretch 4’s” in the NBA, before it became the thing that teams look for. Drafted right out of high school, Lewis had a nice nine-year career with the Seattle Supersonics. But after becoming a free agent at 29-years old, the Orlando Magic signed Lewis to a six year deal worth $118 million.
Why they thought it’d be a good idea to pay that much to someone entering their 30’s is anyone’s guess. To make matters worse, two years into his deal, Lewis was suspended for testing positive for a banned substance, which led to allegations that the prime of his career came as a result of performance-enhancing drugs.
Gilbert Arenas: 6 years, $111 million (2008)
Gilbert Arenas was one of the best 15 players in the NBA during the 2006-2007 season, but the following season, he only played in 13 games as a result of torn MCL. When Arenas became a free agent, he demanded top dollar. Arenas would be given a six-year, $111 million contract by former Wizards General Manager Ernie Grunfeld, despite Arenas’ injury the year prior.
Less than two years later, Arenas would be suspended indefinitely from the NBA after admitting to bringing a firearm into Washington’s arena, as a result of a dispute with teammate Javaris Crittendon.
Tristan Thompson: 5 years, $82 million (2015)
One of the worst kept secrets in the NBA was the fact that the Cleveland Cavaliers were effectively coerced into signing Tristan Thompson to a big money deal, as Thompson was represented by Klutch Sports — the agency so closely associated with a guy named LeBron James, who had returned to Cleveland at that time.
Sure, Thompson had played well in the 2015 NBA Finals (when Cleveland lost to the Golden State Warriors), but he was far from the type of player worth $16+ million per season at the time.
Reggie Jackson: 5 years, $80 million (2015)
Less than six months after acquiring him in a deal with the Oklahoma City Thunder, the Detroit Pistons decided to commit to a long-term relationship with point guard Reggie Jackson, a talented player but enigmatic player who always seemed to have a way to wear down on his teammates.
But that didn’t stop Stan Van Gundy from thinking he could build a legitimate playoff contender on centerpieces like Reggie Jackson and Andre Drummond. In a totally unrelated note, Van Gundy was eventually relieved of his duties in Detroit.
DeMarre Carroll: 4 years, $58 million (2015)
In all fairness, DeMarre Carroll was one of those players who almost nobody would have foreseen being on this list when he signed with the Toronto Raptors in 2015. A talented two-way wing player who shined for an Atlanta Hawks team that won 60 games in 2014-2015, Toronto signed away Carroll thinking he could be another versatile player in their lineup.
But between never really being able to recapture that spark he had in Atlanta, as well as injuries that began to plague him, the Raptors eventually had to send away two draft picks to dump Carroll’s on the Brooklyn Nets.
Matthew Dellavedova: 4 years, $38 million (2015)
Even the most hardcore basketball enthusiast probably had little knowledge of Matthew Dellavedova’s existence, at least prior to the 2015 NBA Finals.
But Dellavedova’s work chasing around Stephen Curry — and some of his on-court antics that toed the line between “gritty” and “dirty” — earned Dellavedova a four-year, $38 million deal with the Milwaukee Bucks, after the Cleveland Cavaliers traded him there. Since arriving in Milwaukee, Dellavedova has averaged less than eight points per game.
Ian Mahinmi: 4 years, $64 million (2016)
Heading into the summer of 2016, it was no secret that the Washington Wizards cleared up enough room for a maximum contract, with the hopes of bringing Kevin Durant — a Washington, D.C.-area native — back home. But Durant spurned the Wizards, leaving them with a ton of salary cap space, and nothing to do with it.
Instead of managing it wisely and saving it for later, they went out and inexplicably threw $64 million at Ian Mahinmi, who averaged 5.1 points and 4.3 rebounds over the prior eight years. After arriving in Washington, Mahinmi has never averaged more than 6 points or 5 rebounds over the course of an entire season.
Nicolas Batum: 5 years, $120 million (2016)
Despite never averaging more than 15 points per game over an entire season, the Charlotte Hornets had to make the decision of whether to offer a big-money contract to Nicolas Batum, whom they acquired from the Portland Trail Blazers the year before. Making the question more complicated was the fact that Batum missed 12 games during the regular season, and another injury in Charlotte’s playoff loss.
The Hornets eventually handed Batum a contract worth $24 million per year, and after him putting up a career season the year after signing said deal, his statistics have steadily declined ever since.
Ryan Anderson: 4 years, $80 million (2016)
The Houston Rockets have never been shy about taking risks with their roster, especially when it comes to putting together the right mix of talent around James Harden. That’s why after striking out on signing both Al Horford and Kent Bazemore in the 2016 free agency period, the Rockets signed Ryan Anderson, who had missed extensive time in each of the prior three seasons, to a deal worth $20 million per year.
In what shouldn’t be any surprise, the Rockets immediately began shopping Anderson just one year later, trying to find a way to get out from underneath his contract.
Bismack Biyombo: 4 years, $72 million (2016)
If you want a good example of why the Orlando Magic spent so much time in the basement of the NBA (prior to their breakthrough 2018-2019 season), look no further than the disastrous deals they’ve made — including the one they handed to forward Bismack Biyombo.
Biyombo never even averaged six points per game during his first five years in the NBA, but a late-season spurt with the Toronto Raptors in 2016 enticed the Magic enough to throw a deal worth $18 million per year in his direction.
In what shouldn’t be any surprise, Biymobo still hasn’t averaged more than 6 points per game ever since, and actually saw his palatable rebounding numbers decrease ever since.
Gorgui Dieng: 4 years, $64 million (2016)
If you were to rank NBA centers, how many would you name before you got to Gorgui Dieng of the Minnesota Timberwolves? At least 20, right? Maybe 25? Maybe more? You could make arguments for any of those. But that didn’t stop Minnesota from giving Dieng, who averaged 8.5 points per game over his first three seasons in Minnesota, a deal worth $16 million per year.
Despite standing almost seven-feet tall, Dieng has yet to average even eight points per game, and is another one of those players on the Timberwolves who’s highly paid but provides very little return on investment.
Timofey Mozgov: 4 years, $64 million (2016)
Another one of the absolutely hideous contracts signed in the summer of 2016, there was absolutely no rhyme or reason to give center Timofey Mozgov a four-year, $64 million contract, as the Los Angeles Lakers did that summer. It was their way of justifying that they “did something” after striking out on free agent signings for years past.
But Mozgov was a complete waste of money, averaging less than 7.5 points per game in one season in Los Angeles. The Lakers traded him to the Brooklyn Nets the next season. The Nets are still paying for this awful deal.
Chandler Parsons: 4 years, $94 million (2016)
The pièce de résistance of the horrific contracts handed out in the summer of 2016, why the Memphis Grizzlies thought it would be a good idea to hand a four-year, $94 million contract to Chandler Parsons, a guy coming off a significant knee injury is beyond baffling.
In three seasons in Memphis, Parsons started 45 of a possible 246 games (18%) and averaged less than 8 points per game. Memphis has done whatever they can to unload his albatross contract.
Allen Crabbe: 4 years, $75 million (2016)
As ace ESPN reporter Brian Windhorst recently characterized the 2016 offseason as “what the hell were we thinking?” Case in point: the contract given to Allen Crabbe of the Portland Trail Blazers.
After averaging 10.3 points per game, Crabbe received a four-year, $75 million offer from Brooklyn; because Crabbe was a restricted free agent, Portland matched that contract to keep him around.
The contract became so cumbersome for the Trail Blazers’ salary cap that they had to trade him in another salary dump just one year after signing him to that deal.
Joakim Noah: 4 years, $72 million (2016)
Sometimes, there’s a reason why basketball professionals are paid to do a job, and why NBA fans aren’t. In many other cases, it’s amazing how basketball professionals are completely oblivious to what most NBA fans can see. Take Joakim Noah, for instance.
When Noah became a free agent at the end of 2016, he was already 31 years old, and missed almost 40% of the games over his past two seasons in Chicago. Almost everyone could see he was totally washed up.
But that didn’t stop the New York Knicks from signing Noah to a four-year, $72 million contract. Unsurprisingly, Noah has only played in 53 of a possible 164 games for New York over the past two seasons.
John Wall: 4-year, $170 million “supermax” contract extension (2017)
After a 2016-2017 season in which he averaged career bests in points (23.1), assists (10.7), and steals (2.0) per game, John Wall was named Third-Team All-NBA after the season, and thus became eligible for a “supermax” contract. In a gesture of goodwill to a guy the Wizards saw as their franchise cornerstone, they handed Wall said supermax extension — which was set to kick in after after his current contract expired in 2019.
Now, the Wizards will be responsible for paying him over $38 million per year starting in 2019-2020, with him coming off a series of injuries that includes a torn Achilles’ tendon. He is now considered to have the worst contract in the NBA.
Otto Porter: 4 years, $106.5 million (2017)
Entering the the 2017 offseason, Otto Porter Jr. of the Washington Wizards was set to become a restricted free agent. The Brooklyn Nets swooped in and offered Porter a 4-year, $106.5 million contract, which forced the Wizards to either match the deal, or lose Porter in free agency with no compensation.
The Wizards clearly chose the former, signing him to a deal that briefly made him the highest-paid player on the team. Less than two years after signing that deal, the Wizards forced themselves into trading away Porter’s deal, to get some relief from the NBA’s luxury tax.
Andrew Wiggins: 4-year, $148 million contract extension (2017)
It’s not that Andrew Wiggins is a “bad player,” per se. And his contract isn’t as horrifically egregious as some others you might find on this list. But the fact of the matter remains the same: Wiggins base salary ($25M+ per year) is among the 20 highest contracts in the NBA at the moment, meaning he’s making more money than a whole slew of All-Stars.
And what has Wiggins accomplished since he arrived in the NBA to deserve that type of money, outside of being the #1 overall pick (thanks to his combination of talents that, one could argue, remain far from being completely unlocked).
Tim Hardaway Jr.: 4 years, $71 million (2017)
When most people expected the New York Knicks to start purging salaries off their bloated payroll in order to begin (yet another) full-scale rebuild, they surprisingly made a run at Tim Hardaway Jr.
Hardaway started his career in New York, and showed promise when he moved on to the Atlanta Hawks, but the fact remains that Hardaway had never started more than 30 games in a season, and yet the Knicks were still comfortable handing him almost $18 million per year on average.
In a totally predictable twist of irony, the Knicks traded away Hardaway less than two seasons later to — you guessed it — start purging salaries of their payroll.
Mason Plumlee: 3 years, $41 million (2017)
In all fairness, the enormous salary cap spike seen by the NBA in the summer of 2016 made salaries of “only” $14 million seemingly a bargain in today’s NBA landscape. That being said, it’s still hard to justify a player like Mason Plumlee making nearly that much (on average) per season.
Sure, Plumlee was a player whom the Denver Nuggets acquired via trade, so they were effectively forced into a position of re-signing him or having made that trade and getting nothing in return. Although in hindsight, that deal looks terrible regardless, considering the Nuggets got Plumlee in exchange for a pick that would turn out to be Jusuf Nurkic.
James Johnson: 3 years, $43 million (2017)
James Johnson represents another case of the classic “contract year” trap. Having made 5 different stops in his NBA career before arriving in Miami in 2016, Johnson averaged more than eight points a game scoring only twice in seven prior seasons. But in his first year in Miami, he saw his scoring output jump up to 12.8 points per game.
In their desperation to remain relevant in the Eastern Conference, the Heat brought back Johnson with a 3-year deal. In each of the first two seasons of said deal, Johnson’s scoring output has steadily decreased.
Chris Paul: 4 years, $160 million (2018)
In all fairness, the Houston Rockets found themselves in something of “no-win” scenario with Chris Paul’s contract situation in the summer of 2018, over the course of the long-term. They acquired him to be the 2nd superstar on the team (next to James Harden), and the catalyst for overcoming the Golden State Warriors in the Western Conference.
The latter clearly hasn’t happened yet, and now Paul is on Houston’s books through 2022, with a contract that’ll cost them almost $160 million — including over $44 million in 2021-2022.
Zach LaVine: 4 years, $78 million (2018)
The Chicago Bulls seemingly had little reservation signing handing almost $20 million per year to guard Zach LaVine, despite the fact that LaVine was coming off a torn ACL injury, which is a drastic injury for someone whose game was almost entirely predicated on his off-the-charts athleticism.
There will be those who tell you that the Bulls were justified in handing LaVine this deal, considering his career year in 2018-2019 (averaging 23.7 points, 4.7 rebounds, and 4.5 assists per game), but how much of those stats really mean anything considering the Bulls ended up winning all of 22 games that season?