The Most Crippling NBA Contracts In Recent History

Basketball | 8/27/19

NBA franchises eagerly seek to hang a championship banner in their arenas, but not every team is fortunate enough to have a player like Michael Jordan or Stephen Curry help achieve that. That’s why there’s substantial importance surrounding the details of signing a player. General Managers can’t give just anybody $80 million for four years. What did they do to earn that? Are they going to propel you towards winning? In hindsight, these offers look horrendous, but at the time, we’re sure upper management believed in their choice wholeheartedly. Take a moment and discover which players received the most detrimental contracts to exist in the NBA.

Chris Webber – $74.4 Million, 15 years (1993)

webber smiles in a Kings jersey
Lisa Blumenfeld/Getty Images
Lisa Blumenfeld/Getty Images

Chris Webber was the number one overall pick in the 1993 draft. Initially drafted by the Orlando Magic, Webber had his rights traded to the Golden State Warriors for Anfernee “Penny” Hardaway. The Warriors signed the rookie to a ludicrous deal.

Webber signed on the dotted line for $74.4 million across 15 years. The insane part was that he had the option to opt-out after one year. After colliding with head coach Don Nelson, Webber indeed opted out and landed on the Kings where he would become a five-time All-Star.

Luol Deng – $72 Million, Four Years (2016)

shooting a jumpshot
Jonathan Bachman/Getty Images
Jonathan Bachman/Getty Images

Towards the end of Kobe Bryant’s tenure with the Los Angeles Lakers, the Lakers must have thrown out their winning pedigree. It was like they forgot how to sign big-name free agents and doing things that helped them win.

Of their many mistakes was inking Luol Deng to this outlandish deal of $72 million across four years. Deng was far from a scrub in 2016, but this contract was beyond crippling for the purple and gold. Besides keeping the bench warm, Deng had no purpose in Los Angeles and eventually reached a buyout with the team.

Joakim Noah – $72.6 Million, Four Years (2016)

holding up his new threads
BRYAN R. SMITH/AFP/Getty Images
BRYAN R. SMITH/AFP/Getty Images

This entry still might ruffle some feathers among the Knicks collectives out there. Leading up to this deal, the last time anyone had seen Joakim Noah, he was traversing through the jungle with a blonde beard.

The upside the Knicks must have seen in Noah is that he was only two years removed from back-to-back All-Star appearances. He also had a Defensive Player of the Year award under his belt, so optimism swirled around New York. “He is still a skilled passer and defensive hustler, but he carries zero cachets elsewhere,” Bleacher Report’s Dan Favale wrote.

Chandler Parsons – $94 Million, Four Years (2016)

dribbling the ball
Abbie Parr/Getty Images
Rob Carr/Getty Images

Chandler Parsons might be the NBA’s greatest scammer. After putting up some borderline all-star stats while playing in Houston and Dallas, he garnered looks from plenty of teams. The 2016 free-agency period was a wild one, but when the Memphis Grizzlies signed Parsons to that lucrative deal, we wonder how many in the front office regretted it right away.

The moment he began playing for the Grizzlies, his stats dropped considerably. Parsons fell off the radar of even “decent” NBA players and is now nothing more than a role player. It’s like he doesn’t want to be in Memphis.

Shawn Kemp – $107 Million, Seven Years (1997)

an older shawn kemp
bdetrick/Twitter
bdetrick/Twitter

Shawn Kemp was once a force to be reckoned with. There was no rim in the NBA that didn’t know his name. Kemp was one of the great players of the late ’90s. He became highly upset when the Seattle Supersonics paid a free agent big bucks, opposed to taking care of the star they already had.

That’s when he demanded a trade and landed on the Cleveland Cavaliers. The Cavs paid him the large sum of money he wanted, but a lockout-shortened season came about in ’98. Kemp fell victim to substance abuse during the lockout, and weight gain began to eat away at this former talent.

Jim McIlvaine – $33.6 Million, Seven Years (1996)

running up court
Otto Greule/Allsport
Otto Greule/Allsport

Speaking of Shawn Kemp, here’s the man that forced him to demand a trade. Jim McIlvaine averaged less than 15 minutes per game in his first two seasons with the Washington Bullets. Then, it was his turn to test free agency, and the Supersonics bit at his length and height. During the ’90s and ’80s, a true center was something teams lusted for.

The deal pretty much tore apart an excellent Seattle team. If this were 2018, McIlvaine would be lucky to see half of what he made back then.

Joe Smith – $1.75 Million, One Year (1998)

GettyImages-51547167
CRAIG LASSIG/AFP/Getty Images
CRAIG LASSIG/AFP/Getty Images

For being the number one overall pick in 1995, Joe Smith never did live up to that hype. He did find a home in Minnesota, lining up alongside Kevin Garnett. His contract extension of ’98 isn’t bad because of the money, but because of the outcome.

Smith agreed to sign the deal “below market value,” to allow the team to pick up other pieces with the remaining money. The Timberwolves also promised to pay him more money later. As a result, the league fined the Timberwolves $3.5 million and took away five first-round picks.

Bryant Reeves – $61.8 Million, Six Years (1998)

posting up
Jason Wise /Allsport
Jason Wise /Allsport

Unless you’re a Grizzlies fan, the name Bryant Reeves might not ring too many bells. “Big Country” played well his first two seasons in the league, averaging 13 points year one and just over 16 the second year.

Then came his free agency and the then-Vancouver Grizzlies gave him $61 million for six years. In came the injury problems and conditioning issues for the rest of his career. Reeves was out of the NBA before that contract was even finished.

Vin Baker – $86 Million, Seven Years (1999)

questioning the ref
Donald Miralle /Allsport
Donald Miralle /Allsport

The questionable moves that the Seattle Supersonics made during the late ’90s might have contributed to the team moving to Oklahoma City. After failing to sign Shawn Kemp, but giving that money to Jim McIlvane, they made another mistake.

In the trade that shipped Kemp out of town, the Supersonics received Vin Baker in return. Once Baker made it to Seattle, his promising career began to go down the drain primarily due to his substance abuse off the court.

Allan Houston – $100.4 Million, Six Years (2001)

michael jordan and allan houston
KMazur/WireImage
KMazur/WireImage

Ever since the Bulls Michael Jordan era, the New York Knicks have been abysmal. They haven’t been close to making a Finals appearance in decades. With such bad luck, they’ve desperately tried to become a contender by any means.

That includes signing players they think are worth it and will help carry them back to relevancy. One of their mistakes happened in 2001 when they gave Allan Houston way too much money. The deal was so bad that the NBA created a new collective bargaining agreement, effectively allowing a team to amnesty one contract. It became known as the “Allan Houston Rule.”

Raef LaFrentz – $70 Million, Seven Years (2002)

being guarded by Rasheed Wallace
Ronald Martinez/Getty Images
Ronald Martinez/Getty Images

Raef LaFrentz had an All-American college career at the University of Kansas. He became the third overall pick in the 1998 draft when the Denver Nuggets selected him. He averaged a career-high during the ’01-’02 season of 14.9 points-per-game, and that was enough for the Dallas Mavericks to bite.

LaFrentz saw a big payday, but the Mavericks didn’t get much return from their investment. After his free-agent bust in Dallas, Portland tried their luck with LaFrentz after offering him a decent amount. That didn’t turn out well, either.

Stephon Marbury – $74 Million, Four Years (2003)

dribbling the ball in traffic
Jeff Gross/Getty Images
Jeff Gross/Getty Images

We get it, Stephon Marbury was a player you couldn’t lose hope in. He was a fantastic talent, but his ego was his downfall. After burning out in two different cities, the Phoenix Suns thought it would be smart to give Marbury a whirl.

No surprise here, but the Suns ended up trading him away in 2004. He didn’t last long in Phoenix, but the Knicks wound up paying him all the money he wanted.

Erick Dampier – $70 Million, Seven Years (2004)

looking on
Ronald Martinez/Getty Images
Ronald Martinez/Getty Images

Erick Dampier or what Shaquille O’Neal called him, “Erica Dampier” was big, but he didn’t always use his size to his advantage. His best year statistically was 2004, so the Dallas Mavericks took a chance on him via trade. He was another center averaging a double-double, so why not?

After agreeing to the big bucks, the rest of his time in Dallas was laughable. He went from averaging a double-double to less than ten points and nine rebounds per game.

Andray Blatche – $35 Million, Five Years (2007)

pre game ritual
Rob Carr/Getty Images
Rob Carr/Getty Images

Would you sign a player to a five-year deal worth $15 million after they averaged 3.2 points and 2.7 rebounds in 85 career games? No, you wouldn’t, but for some reason, Washington General Manager Ernie Grunfeld did and even added $28 million to the Andray Blatche contract.

There was nothing that indicated Blatche deserved that type of payday. His reputation was that of a poor work ethic and being immature. No surprise here, but Blatche wildly underperformed after inking the deal.

Rashard Lewis – $118 Million, Six Years (2007)

pointing to teammate
Streeter Lecka/Getty Images
Kevin C. Cox/Getty Images

Before NBA teams searched for “stretch 4’s,” Rashard Lewis was one of the originals. Lewis played wonderfully during his first nine years in Seattle, and no one can debate that. We do have the right to question this decision by the Orlando Magic, though.

Heading into his 30’s, they decided to give Lewis a very lucrative deal. To make things worse, two years into it, Lewis got suspended for using a banned substance. Such news led to allegations that his prime came from using PEDs.

Gilbert Arenas – $111 Million, Six Years (2008)

point guard for the wizards
Christian Petersen/Getty Images
Christian Petersen/Getty Images

The contract Gilbert Arenas received in 2008 wasn’t a bad one. Arenas was a top 15 player in the league around this time, so the Wizards would have been silly not to secure the star point guard. He was coming off of an MCL tear the previous year, but his game didn’t revolve around much explosiveness.

The only thing that made this deal “bad” was the fact that Arenas admitted to bringing a firearm to the arena, causing his indefinite suspension less than two years after signing.

Reggie Jackson – $80 Million, Five Years

pumped during a game
Gregory Shamus/Getty Images
Gregory Shamus/Getty Images

After the Oklahoma City Thunder passed on giving Reggie Jackson the type of money he thought he deserved, the Detroit Pistons were desperate for a point guard. No, Jackson wasn’t terrible, but he was best suited as a sixth man providing help when he can.

Coach Stan Van Gundy thought the addition of Jackson would be perfect for a legitimate playoff contender. He assumed Jackson and Andre Drummond would be enough. Van Gundy was eventually relieved of his duties.

Matthew Dellavedova – $38 Million, Four Years (2015)

calling the play
Stacy Revere/Getty Images
Stacy Revere/Getty Images

If you are a casual NBA enthusiast, we’re willing to bet you had no clue who Matthew Dellavedova was before the 2015 NBA Finals. Even the savviest of fans might not have had an idea about him. Then, he showed us how much hustle he has in that small frame.

Dellavedova pestered Stephen Curry so well, he earned a four-year deal with the Milwaukee Bucks that was more than he should have ever received. Once he landed in Milwaukee, Delladova averaged less than eight points per game.

Nicolas Batum – $120 Million, Five Years (2016)

Nic batum hornets
Michael Reaves/Getty Images
Michael Reaves/Getty Images

When Nicolas Batum played for the Portland Trailblazers, he was an excellent sidekick to Damian Lillard. He could defend, shoot the corner three, and he was athletic. General Managers loved all of those qualities, but the Blazers didn’t want to pay him too much.

Batum tested free-agency, and the Charlotte Hornets (or owner Michael Jordan) thought five-years, $120 million would be worth it. We’ll add that Batum did have a career season one year after signing. Since then, his numbers have steadily fallen.

Bismack Biyombo – $72 Million, Four Years (2016)

orlando magic player Bismack Biyombo
Sam Greenwood/Getty Images
Sam Greenwood/Getty Images

There are only a handful of players in the NBA that should be signing $72 million contracts for four years. Bismack Biyombo is not one of them. This is a prime example of why the Orlando Magic haven’t done anything worthwhile since the departure of Dwight Howard.

The big guy Biyombo never averaged more than six points per game his first five years in the league. He did have a late-season spurt with the Toronto Raptors that must have enticed the Magic enough to ink this outlandish deal.

Khris Middleton – $178 Million, Five Years (2019)

shooting layup
Stacy Revere/Getty Images
Stacy Revere/Getty Images

Khris Middleton won the 2019 free agency show. No one expected a player coming from the developmental league to ever earn himself a max contract extension on a championship contending team. It’s unheard of in the NBA. His path leading up to that point includes an adorning story of hard work and patience, but let’s be honest.

The Bucks effectively ended their chances of winning a championship in the upcoming seasons by wasting all that money on Middleton. Is Middleton a great player, yes. Is he going to help you win a title as the second best player on your team, no.

Adonal Foyle – $42 Million, Six Years (2004)

basketball
JON HATCH/AFP/Getty Images
JON HATCH/AFP/Getty Images

If you want to talk about let downs, then you have to mention Adonal Foyle. A former 8th overall draft pick, Foyle would average less than six points per game during his first seven seasons.

That didn’t stop the Golden State Warriors from keeping faith in him and giving him a lucrative deal. Immediately after signing, his stats dropped even lower! The Warriors have to waive him with $29.2 million remaining on his expensive contract.

Eddy Curry – $60 Million, Six Years (2005)

in the post
Nick Laham/Getty Images
Nick Laham/Getty Images

Another player that failed to live up to his hype is Eddy Curry. At 22, Curry was hospitalized with an irregular heartbeat. After refusing to get tested for it, the Knicks paid it no mind and brought him over via trade and signed him to an insane deal.

His tenure playing at Madison Square Garden was a disaster. The health issues were one thing, but he constantly struggled with his weight, and would act immature in public spaces. He didn’t perform well at all.

Jerome James – $30 Million, Five Years (2005)

smiling
Elsa/Getty Images
Elsa/Getty Images

To every New York Knicks fan reading this article, we apologize. It isn’t your fault your franchise hasn’t succeeded in years. Blame the front office for every questionable decision they’ve made since the last time they’ve made it to the Finals.

In 2005, they thought they had a winner in Jerome James, even after he spent a career bouncing around teams on his way to turning 30. He wasn’t LeBron James, he wasn’t going to give you monumental results in his thirties. The Knicks knew it was bad as soon as he arrived to training camp out of shape.

Tristan Thompson – $82 Million, Five Years (2015)

looking up
Jason Miller/Getty Images
Jason Miller/Getty Images

This one is completely debatable for both parties. There aren’t many players left in the NBA like Tristan Thompson. That’s either a good or bad thing depending on how you view the league. He’s a hustle player with a spotty jump shot that can grab a ton of rebounds.

Thanks to being represented by Klutch Sports, Thompson managed to secure a decent deal. One could argue he could have asked for more, while the stats would argue he didn’t deserve that much. His value to Cleveland is undeniable, but his worth around the league is questionable.

Derrick Rose – $15 Million, Two Years (2019)

shooting free throws
David Berding/Getty Images
David Berding/Getty Images

This contract is worse for the player than it is for the franchise. Coming off a career-year season in which he scored an astounding 50 points, Rose entered free-agency. After staying on the market for a while, the Pistons elected to give the former MVP his pay day.

The only thing about it is that Rose will now be heading to Detroit, a place where careers vanish. After working so hard to gain relevancy again after so many injuries, Rose might have taken three steps back for little money.

DeMarre Carroll – $58 Million, Four Years (2015)

holding the ball
Vaughn Ridley/Getty Images
Vaughn Ridley/Getty Images

Full disclosure, at one point in time, DeMarre Caroll was completely worth this deal. During his time in Atlanta, his play was pivotal and that’s what earned him this great contract in Toronto in the first place.

Sadly, going to play in another country must have been too much for him to handle as he never recaptured that spark he had in the States. The Raptors eventually had to trade him away to Brooklyn for draft picks.

Ian Mahinmi – $64 Million, Four Years (2016)

running
Scott Taetsch/Getty Images
Scott Taetsch/Getty Images

The summer of 2016 was an interesting one. Everyone wanted to play the Kevin Durant sweepstakes and each team thought they each had an equal chance. The Wizards thought they sat higher on the leader board because Durant is from the D.C. area. He chose the Warriors.

That left the Washington Wizards with a bunch of money. They wasted it on a player who averaged 5.1 points and 4.3 rebounds the prior eight years. Once Ian Mahinmi went to the Wizards, his stats fell even more.

Ryan Anderson – $80 Million, Four Years (2016)

passing the ball
Hannah Foslien/Getty Images
Hannah Foslien/Getty Images

Known to take risks with their roster, the Houston Rockets took another chance with stretch big man Ryan Anderson. He certainly fit the scheme that the Rockets wanted to run with, but Anderson just didn’t have it like he once did.

The Rockets missed out on other big names in 2016, which is why they had to get someone. One year later after picking up the sharp-shooter, they added him to the trading block in hopes to get out of that wonky contract.

Gorgui Dieng – $64 Million, Four Years (2016)

bending over breathing
Zhong Zhi/Getty Images
Zhong Zhi/Getty Images

The Minnesota Timberwolves have been a dumpster fire since Kevin Garnett left in his prime. Jimmy Butler arrived and kind of patched things up, but he left and made the flames bigger. In 2016, the organization contributed to the scorching disaster by giving Gorgui Dieng more money than he needed.

No knock to Dieng, because he’s still relatively early in his career, but he’s unproven. Playing behind Karl Anthony Towns isn’t doing much for him and he isn’t bringing much value to the team.

Timofey Mozgov – $64 Million, Four Years (2016)

the center
Thearon W. Henderson/Getty Images
Thearon W. Henderson/Getty Images

Here is yet another concerning move that the Lakers made post-Bryant era. Not only did they bring in Luol Deng with that insane contract, but they did the same thing with Timofey Mozgov. Granted, he was able to contribute more and did, but he wasn’t worth that much for their roster.

He wound up averaging less than 7.5 points per game in his first season with Los Angeles. They somehow found a way to ship him to Brooklyn so they could deal with that messy contract.

Allen Crabbe – $75 Million, Four Years (2016)

Allen Crabbe looking
Matthew Stockman/Getty Images
Matthew Stockman/Getty Images

Allen Crabbe used to be the third core player in Portland that complimented Lillard and McCollum. After performing well during his contract season, he sparked interest in a lot of teams. As a restricted free agent, you can only get offers that your current team has a chance to match or they have to let you go.

The Brooklyn Nets offered Crabbe more than money than he would have received anywhere else so Portland had no choice but to let him walk. He hasn’t done much since landing in Brooklyn.

Otto Porter – $106.5 Million, Four Years (2017)

making a shot
Elsa/Getty Images
Elsa/Getty Images

Going into the 2017 free agency period, Otto Porter was a restricted free agent. The Wizards didn’t know what to expect, so they were blindsided by the offer the Nets gave their young player.

Washington didn’t want to see him go, so they had to match that extremely high offer to retain Porter. Less than two years after matching it, they were forced to trade him to gain some relief from the NBA’s luxury tax.

Andrew Wiggins – $148 Million, Four Years (2017)

Wiggins shooting
Harry How/Getty Images
Harry How/Getty Images

This is a tricky one. Andrew Wiggins is a former number one overall pick that carried tremendous upside. His ceiling was as high as anyone’s but as the years went by, he didn’t quite deliver. Wiggins shows flashes, but he’s never consistent.

This could turn out to be Minnesota’s worst move, or a very clever decision. All Wiggins needs to do is play at high level every night and things will be fine. Sadly, he’s still yet to do that and this contract just hit the half-way point.

Tim Hardaway Jr. – $71 Million, Four Years (2017)

pumped up
Mike Stobe/Getty Images
Mike Stobe/Getty Images

With the Knicks in dire need to spark some type of magic in the mecca of basketball, they’ve made sporadic signings. Mostly, they tend to get athletes who show potential but don’t follow through. The verdict may still be out on Tim Hardaway Jr., but he isn’t on the Knicks anymore.

After starting his career in New York, it made sense for the Knicks to bring him back after he showed more promise while playing with the Atlanta Hawks. All he’s been so far is a broken promise.

Mason Plumlee – $41 Million, Three Years (2017)

dunking
Matthew Stockman/Getty Images
Matthew Stockman/Getty Images

If you weren’t aware, the salary caps for NBA teams increased dramatically in 2016. IF you see a lot of outrageous deals from that year, you know why. Still, the Denver Nuggets didn’t make a wise decision with this move.

After acquiring Mason Plumlee via trade, they had to keep him or they would have got nothing in return from the exchange. Plumlee must have thanked his agent a thousand times for this contract. The Nuggets could have spent that money elsewhere to make them even more of a threat.

James Johnson – $43 Million, Three Years (2017)

driving in the paint
Tom Szczerbowski/Getty Images
Tom Szczerbowski/Getty Images

Inflated salaries means a lot of questionable signings. All it takes is a player to play consistent enough for a single year and teams will think they are going to help over the long run. They need to remember to look at the body of work, not just the high points.

The Miami Heat picked up James Johnson after he made five stops on other teams. Granted, his first season with the Heat, he did increase his scoring output, but the two years after signing the deal, his scoring decreased steadily.

Dion Waiters – $52 Million, Four Years (2017)

talking
Michael Reaves/Getty Images
Michael Reaves/Getty Images

Dion Waiters never materialized into a player that teams can depend on night in and night out. Oklahoma City tried their luck with him, as did the Cleveland Cavaliers. His impact wasn’t everlasting, which how he found himself on the Heat. There, he became a somewhat effective scorer for a team that lacked one.

The Heat pulled the trigger and signed him to a great deal in the new money era. That same season, he struggled to find his shot, shooting just over 30 percent from three. He only averaged 10.7 points per game that year as well.

Gordon Hayward – $127 Million, Four Years (2017)

gordon hayward
Maddie Meyer/Getty Images
Maddie Meyer/Getty Images

This selection is tough. It wasn’t anyone’s fault that Gordon Hayward suffered a gruesome injury in the first five minutes playing for a new team. After missing the entire season, Hayward came back the following year (2018) and played sub par.

We understand he still has to get his legs back under him, but if he fails to do so, then Boston can be looking at waste of money wearing number 20. Time will tell for faithful in Boston.

Kobe Bryant – $48.5 Million, Two Years (2013)

pointing
Harry How/Getty Images
Harry How/Getty Images

Coming off his Achilles injury earlier in the year, Kobe Bryant managed to get the Lakers to sign him to an expensive contract. The MVP would see $23.5 million the first year and then $25 million the next. Bryant said he deserved it, which he did, but the Lakers organization needed that extra money to bring in more talent.

As a result, they didn’t have enough money bring in enough good talent during Bryant’s final years and it began a domino effect. See Luol Deng and Timofey Mozgov from earlier in this post.