10 Most Notorious Lose-Lose Trades In NBA History
· Yahoo Sports
Most bad NBA trades are pretty easy to remember because one team gets destroyed and the other spends the next five years laughing about it. Don’t think so? Ask Mavericks fans about the Luka trade, or Clippers fans about the PG move while Shai builds a dynasty in OKC.
Luckily for them, this time we’re talking about deals where both sides walked in thinking they had done something huge for their contending cases, then a couple of years later, everybody involved was kinda wondering what the hell happened.
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Some teams eventually recovered value from pieces they got in these trades, so “lose-lose” doesn’t mean every single asset became useless. It’s more about the actual goal of the deal. Did the contender get the star run it expected? Did the rebuilding team get pieces that changed its future? In these 10 cases, usually the answer on both sides was no.
And some of these looked incredible for about five minutes. Dwight Howard joining Kobe Bryant, Carmelo Anthony making a Big Three with Russell Westbrook and Paul George, Kyrie Irving getting his own team in Boston, James Harden joining Joel Embiid… Yeah, basketball had other plans.
10. Lakers Acquire Dwight Howard In A Blockbuster Deal With The Magic
Los Angeles Lakers Receive: Dwight Howard, Chris Duhon, Earl Clark
Orlando Magic Receive: Nikola Vucevic, Aaron Afflalo, Al Harrington, Moe Harkless, Josh McRoberts, Christian Eyenga, three first-round picks, two second-round picks
Philadelphia 76ers Receive: Andrew Bynum, Jason Richardson
Denver Nuggets Receive: Andre Iguodala
On paper, this was absolutely crazy once it happened, because Dwight Howard had just finished 2011-12 with 20.6 points, 14.5 rebounds, and 2.1 blocks, and now the Lakers were putting the three-time Defensive Player of the Year next to Kobe Bryant, Pau Gasol, and Steve Nash. Instead, they went 45-37; Kobe destroyed his Achilles trying to drag them into the playoffs, Dwight finished at 17.1 points, 12.4 rebounds, and 2.4 blocks; then the Spurs swept them 4-0 in Round 1. Howard immediately left for the Rockets in free agency, so the whole superstar experiment lasted one season.
The funniest part is that the other teams didn’t exactly celebrate either. Andrew Bynum never played a single game for the 76ers because of his knees, while Andre Iguodala spent one year with the Nuggets before leaving for the Warriors. The Magic definitely salvaged the most here because Nikola Vucevic eventually became a two-time All-Star and lasted nearly nine seasons with them, but that team still crashed to 20 wins immediately and spent years rebuilding without much success getting back to the postseason in the short run.
So yeah, Orlando survived it better than everybody else, as crazy as it sounds, but the actual blockbuster mostly gave us one miserable Lakers season, zero Bynum games in Philadelphia, and one Iguodala season in Denver. For a trade involving four teams and that many huge names, that’s pretty rough.
9. The Carmelo Anthony Big Three Was So Doomed
Oklahoma City Thunder Receive: Carmelo Anthony
New York Knicks Receive: Enes Kanter, Doug McDermott, 2018 second-round pick
I absolutely understand why the Thunder did this: Russell Westbrook was coming off an MVP season, Paul George had just arrived, and Carmelo Anthony had still scored 22.4 points per game for the Knicks the year before. Oklahoma City basically built the most 2017 Big Three imaginable and paid Enes Kanter, Doug McDermott, and one second-round pick to do it. That’s not exactly a terrifying price for a 10-time All-Star.
Then Melo had the worst scoring season of his career to that point. His role dropped hard, and he finished with 16.2 points, 5.8 rebounds, and only 1.3 assists while shooting 40.4% from the field and posting a brutal 50.3% true shooting mark. The Thunder won 48 games but got bounced 4-2 by the Jazz in the first round, and by July they were already attaching a protected first-round pick to Anthony just to turn his contract into Dennis Schroder. One year. That’s all the experiment got.
New York didn’t really get a rebuild starter either after moving their most illustrious player of the entire century (before Jalen Brunson showed up). Kanter had a productive 14.1 points and 11.0 rebounds in his first season, but he was waived before finishing Year 2. McDermott lasted 55 games before getting moved again, and they went through horrible cycles for almost half a decade.
Nobody got ruined here because the original price was pretty low, which keeps it at No. 9, but nobody really won either. The Thunder got one disappointing playoff run, and the Knicks got temporary pieces for the biggest star they had in years.
8. Chris Webber And Allen Iverson Never Became What Philly Imagined
Philadelphia 76ers Receive: Chris Webber, Matt Barnes, Michael Bradley
Sacramento Kings Receive: Kenny Thomas, Corliss Williamson, Brian Skinner
I know the trade details sound crazy, but in 2005, this move was aimed at being pretty decent. Chris Webber was still producing 21.3 points, 9.7 rebounds, and 5.5 assists for the Kings when the 76ers paired him with Allen Iverson, who was right in the middle of a 30.7-point season. Webber wasn’t prime C-Webb anymore at 31, but getting that level of scorer and passer next to Iverson felt like a pretty serious swing for a team in their last hope.
Sadly for everyone, it never really clicked. Webber shot only 39.1% from the field across his first 21 games with the 76ers, dropping to 15.6 points, 7.9 rebounds, and 3.1 assists; then Philadelphia went 43-39 and lost 4-1 to the Pistons in Round 1. He actually bounced back statistically the next year with 20.2 points and 9.9 rebounds, except the team got WORSE, finished 38-44, and missed the playoffs. By January 2007, Philadelphia bought him out, and the whole Iverson-Webber partnership was over.
Sacramento didn’t exactly uncover its next core in return. Kenny Thomas became a starter, while Corliss Williamson and Brian Skinner were rotation pieces, but nothing in that package replaced an era-defining player. The Kings lost in the first round in 2005, again in 2006, and then didn’t make the playoffs for another 16 years.
Basically, Philly got the name but not the old player, while Sacramento got depth but no real centerpiece. It was the end of something for both teams more than the beginning of anything.
7. Jimmy Butler Was Amazing For Such A Short Time
Philadelphia 76ers Receive: Jimmy Butler, Justin Patton
Minnesota Timberwolves Receive: Robert Covington, Dario Saric, Jerryd Bayless, 2022 second-round pick
The annoying thing for Philadelphia is that Jimmy Butler actually worked, contrary to the C-Webb trade above. Butler gave the 76ers 18.2 points, 5.3 rebounds, and 4.0 assists after the deal, then turned into probably their most reliable perimeter player once the playoffs got hard. Against Toronto, he was at 22.0 points, 6.9 rebounds, and 5.6 assists, and Philadelphia came literally one Kawhi Leonard bounce away from overtime in Game 7.
Why is this trade here then? Well, I bet that you already know what happened in his Sixers tenure. Only months after the trade, due to financial reasons and the 76ers wanting Tobias Harris over him, Jimmy just left.
Butler landed with the Heat that summer in a sign-and-trade, and watching him take Miami to multiple Finals afterward made the whole thing hurt way more. Philadelphia had traded Robert Covington and Dario Saric, two actual rotation players, for around eight months of Butler basketball. They had the right player in the building and somehow couldn’t make it last since they wanted Ben Simmons handling the main creative load, and didn’t want to give Butler the max he asked for.
Minnesota’s return wasn’t terrible, it just didn’t turn into much there. Covington was a perfect defensive wing in theory but played only 48 games for the Wolves before being dealt again, Saric lasted 68 games before Minnesota moved him to Phoenix, and Bayless was basically salary. The Wolves won 36 games in 2018-19 and went straight back into the lottery.
Philadelphia came much closer to getting a title, which is why this isn’t higher, but the ending was horrible for both. Minnesota turned an All-NBA player into temporary pieces, while the 76ers rented Butler long enough to discover he fit, then watched him become a franchise legend somewhere else.
6. The DeMarcus Cousins Trade Got Destroyed By One Injury
New Orleans Pelicans Receive: DeMarcus Cousins, Omri Casspi
Sacramento Kings Receive: Buddy Hield, Tyreke Evans, Langston Galloway, 2017 first-round pick, 2017 second-round pick
This is maybe the saddest trade here, because for a while, it actually looked like the Pelicans had finally pulled it off. They made a move to acquire DeMarcus Cousins next to Anthony Davis at the 2017 trade deadline, getting ready for the following season.
The fit was completely ridiculous offensively, and in 2017-18, Cousins was giving New Orleans 25.2 points, 12.9 rebounds, and 5.4 assists with 1.6 steals and 1.6 blocks. A center dropping 25-13-5 before basically every big man started passing and shooting threes like guards was insane.
Then January 26 happened. Cousins tore his Achilles against the Rockets, his season ended after only 48 games, and he never played for the Pelicans again. New Orleans actually went on to sweep Portland without him before losing to Golden State, then Cousins signed with the Warriors that summer. The dream AD-Cousins frontcourt basically got 65 regular-season games together across two seasons and zero playoff games.
Sacramento at least found Buddy Hield, who became a 20-point scorer and eventually helped bring back Domantas Sabonis years later, so I wouldn’t pretend the Kings got nothing. The problem was everything around it. The first-round pick turned into a draft-night move for Justin Jackson and Harry Giles, neither became a core piece, and Sacramento continued its playoff drought for another six seasons.
This one almost feels unfair to call lose-lose because an Achilles injury isn’t some front-office mistake. Still, that’s how the trade played out. New Orleans gambled on maybe the nastiest frontcourt in basketball and lost Cousins before getting a single playoff run from it, while Sacramento moved its franchise star without landing another cornerstone in the actual deal.
5. The Porzingis Trade Didn’t Give Either Team A Solution
Dallas Mavericks Receive: Kristaps Porzingis, Tim Hardaway Jr., Courtney Lee, Trey Burke
New York Knicks Receive: Dennis Smith Jr., DeAndre Jordan, Wesley Matthews, two first-round picks
The Knicks traded a 23-year-old Kristaps Porzingis because the relationship had completely fallen apart, while the Mavericks thought they had just found Luka Doncic’s co-star for the next decade. Honestly, both ideas made sense. Porzingis was coming off an All-Star season with 22.7 points and 2.4 blocks before tearing his ACL, and putting a 7-foot-3 shooter next to Luka sounded disgusting.
There were good moments. Porzingis had 20.4 points, 9.5 rebounds, and 2.0 blocks in 2019-20, then 20.1 points and 8.9 rebounds the following year, but his body never really let Dallas build continuity. He played 57 games, then 43, then 34 before the Mavericks finally moved him to the Wizards in February 2022 for Spencer Dinwiddie and Davis Bertans. Dallas gave up two first-rounders for KP and three years later was basically ready to move on from the whole experiment.
New York’s grand plan wasn’t much better. Dennis Smith Jr. fell out of the rotation and got traded, Jordan and Matthews were gone within months, and the cap space created by moving Porzingis and the contracts attached to him was supposed to help the Knicks chase Kevin Durant and Kyrie Irving, but both signed with Brooklyn instead.
The picks gave New York some value, and Tim Hardaway Jr. was genuinely good for Dallas, so there were a few wins inside the deal. The main goals still failed. Dallas didn’t find Luka’s long-term co-star, and the Knicks didn’t turn Porzingis into another franchise move, as even their tanking attempt for Zion Williamson failed and ended with RJ Barrett at No.3 in the Draft.
4. Shaq Basically Ended The Seven Seconds Or Less Suns
Phoenix Suns Receive: Shaquille O’Neal
Miami Heat Receive: Shawn Marion, Marcus Banks
I was too young to understand this trade back then, and now, I think I have less of an idea of why the Suns did it. Phoenix had spent years running around everybody with Steve Nash, Amar’e Stoudemire, and Shawn Marion, then, in February 2008, they suddenly decided the answer was a 35-year-old, 325-pound Shaquille O’Neal. They needed more size for teams like the Spurs, so the Suns traded one of the most versatile forwards for basically the total opposite type of player.
Shaq wasn’t terrible either. That’s what makes it stranger. He put up 13.3 points and 10.4 rebounds in his first 33 regular-season games in Arizona, then had a full revival in 2008-09 with 17.8 points, 8.4 rebounds, and 1.4 blocks on 60.9% from the field, making the All-Star team and All-NBA Third Team at 36 years old.
The team results were the issue. Phoenix lost 4-1 to San Antonio in the 2008 first round, then missed the playoffs completely at 46-36 the following year. By summer 2009, Shaq was already traded again, this time to Cleveland.
Miami didn’t get a long-term building block either. Shawn Marion lasted 58 games across two seasons, scoring 12.0 points with 8.7 rebounds in 2008-09 before the Heat flipped him for Jermaine O’Neal from the Raptors.
Phoenix changed its whole identity for Shaq and never won another playoff series with him. Miami got out of Shaq’s money but didn’t keep Marion. Two famous names changed teams, everybody got excited, and barely a year later both were somewhere else.
3. Kyrie Irving To Boston Somehow Went Bad For Everyone
Boston Celtics Receive: Kyrie Irving
Cleveland Cavaliers Receive: Isaiah Thomas, Jae Crowder, Ante Zizic, 2018 first-round pick, 2020 second-round pick
This one looked like Boston had absolutely robbed Cleveland at first. Kyrie Irving was only 25, coming off 25.2 points on 47.3% from the field and 40.1% from three, and the Celtics were getting him without giving up Jayson Tatum or Jaylen Brown. The Cavaliers got Isaiah Thomas with a damaged hip, Jae Crowder, Ante Zizic, and Brooklyn’s 2018 first-round pick. Pretty easy winner, right? Not really.
Kyrie was great individually, including 24.4 points in his first season and 23.8 points with 6.9 assists in his second, but Boston’s weirdest achievement was reaching the 2018 Eastern Conference Finals while he was injured. One year later, he was healthy, the Celtics entered the playoffs with championship expectations, and everything fell apart against the Bucks. Irving shot 35.6% from the field and 21.9% from three as Boston lost four straight after winning Game 1, then he left for the Nets in free agency with a dramatic exit saga.
Cleveland’s return went sideways even faster. Thomas lasted only 15 games, producing 14.7 points on 36.1% from the field, before he was shipped to the Lakers. Crowder was also moved at that deadline, Zizic never became a rotation piece, and LeBron James left that summer anyway.
Collin Sexton, selected with the Brooklyn pick, saved this from being a total disaster for the Cavs because he became a legit 20-point scorer. Still, Boston traded for a superstar who walked after two years, while Cleveland basically restarted the franchise twelve months later. Nobody imagined that ending.
2. Russell Westbrook To The Lakers Blew Up Everything
Los Angeles Lakers Receive: Russell Westbrook, three second-round picks
Washington Wizards Receive: Kyle Kuzma, Kentavious Caldwell-Pope, Montrezl Harrell and additional assets through the expanded five-team trade
The Lakers had won the championship less than a year earlier and somehow talked themselves into breaking apart the exact roster that worked around LeBron and Davis. Kentavious Caldwell-Pope was an elite 3-and-D; Kyle Kuzma had accepted a smaller role, but got packaged with Montrezl Harrell and the No. 22 pick to bring home Westbrook.
At the time, he was coming off 22.2 points, 11.5 rebounds, and 11.7 assists for Washington, so I get the star logic. The fit logic? Yeah, that was a disaster waiting to happen, since only a year earlier they completely disrespected him in the bubble with Houston, so I never understood their idea.
Someway and somehow, it was even worse than expected, as Westbrook still had 18.5 points, 7.4 rebounds, and 7.1 assists, but the Lakers went 33-49, finished 11th in the West, and didn’t even make the Play-In. Their offense ranked 22nd, their defense 21st, and a LeBron-AD-Russ superteam was basically out of contention before April. Less than two years after spending a first-round pick to get Westbrook, Los Angeles had to attach another first-round pick just to move him.
Washington definitely did better in pure value. Kuzma became a 20-point scorer, KCP remained solid, and Harrell gave them bench production, but the Wizards went only 35-47 the next season and missed the playoffs anyway. None of it changed the direction of the franchise.
So the Wizards won the transaction on paper, sure. In terms of actual basketball results, neither side went anywhere. The Lakers destroyed a contender’s roster balance, while Washington turned Russ into decent pieces and stayed completely stuck.
1. James Harden For Ben Simmons Was A Total Mess
Philadelphia 76ers Receive: James Harden, Paul Millsap
Brooklyn Nets Receive: Ben Simmons, Seth Curry, Andre Drummond, 2022 first-round pick, 2027 first-round pick
This might be the perfect lose-lose trade because both teams were basically exchanging giant headaches and convincing themselves the other headache would be easier.
James Harden wanted out of Brooklyn barely a year after arriving, while Ben Simmons hadn’t played all season after his ugly ending with Philadelphia. The 76ers finally gave Joel Embiid an elite perimeter creator, and the Nets got a 25-year-old three-time All-Star, one of the best shooters in basketball in Seth Curry, Andre Drummond, and two first-round picks. You could very easily talk yourself into either side winning that day.
Philadelphia got closer. Harden led the NBA with 10.7 assists in 2022-23 and helped the 76ers win 54 games, but the whole thing ended exactly where every Embiid era kept ending: Round 2. They actually led Boston 3-2 before losing Games 6 and 7, and Harden finished that series at 22.0 points and 8.0 assists while shooting 42.2% from the field. His last two games were brutal, then a contract fight with Daryl Morey exploded over the summer, and Harden demanded another trade. By November, he was a Clipper.
The Nets somehow had it worse. Simmons never got remotely close to his level, injuries wrecked his future, Curry and Drummond were short-term pieces, and the entire Durant-Irving-Harden era collapsed anyway. The 2027 first-round pick still gives that side of the trade some unfinished business, but the actual idea of Simmons becoming part of Brooklyn’s next core never happened.
That’s what makes this the ultimate No. 1 in my opinion. The 76ers traded Simmons because the relationship was cooked, Brooklyn traded Harden because the chemistry was dying, and somehow both teams were shopping their new centerpiece again before long.