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NBA fans are already calling the Luka Doncic for Anthony Davis trade the worst trade in NBA history, and the two stars haven't even stepped on the court for their new teams yet. Fans feel that way because it is hard to wrap your head around why the Dallas Mavericks could think it was a good idea to trade a 25-year-old who is one of the best players in the NBA and already has a fringe Hall of Fame career. Especially when you only get one first-round pick and an aging and past-his-prime Anthony Davis in return.
Who knows, though, maybe this trade will work out for Dallas in the end. We can't truly make any judgments until years down the road when hindsight has set in. Still, the trade that is considered a fleece got us wondering about the worst trades in NBA history, so we decided to go to ChatGPT for help. After all, trade season is in full force with the 2025 NBA trade deadline just around the corner. So, check out the gallery to see what artificial intelligence has to say.
1. Kevin Garnett to the Boston Celtics (2007)
ChatGPT summary:
Trade Details:
- Boston Celtics receive: Kevin Garnett
- Minnesota Timberwolves receive: Al Jefferson, Ryan Gomes, Sebastian Telfair, Gerald Green, and draft picks (including the 5th overall pick in 2009, which turned out to be Wayne Ellington).
Why It’s One of the Worst Trades:
This trade transformed the Celtics into instant contenders and resulted in a championship in 2008, but for the Timberwolves, it was a brutal move. While Minnesota got a decent haul of players, none of them turned into the superstar-level talent they expected. Al Jefferson showed promise but never became a true franchise player. Meanwhile, players like Telfair, Green, and Gomes were merely role players at best. The Timberwolves had been in the wilderness for years after the trade, and while the draft picks didn’t yield much (Wayne Ellington was not a game-changer), the trade effectively took away their best player and left them with little to show for it.
ClutchPoints analysis:
Ironically, we'd consider a different trade involving Kevin Garnett to be one of, if not the worst trade of all time. That would be the 2013 deal that sent the washed-up versions of him, Paul Pierce, and Jason Terry to the Brooklyn Nets for a surplus of draft assets. The aging trio were clearly past their primes and did next to nothing in Brooklyn, while the Nets struggled over the coming years and ended up giving the Celtics draft picks near the top of the draft. Two of those picks turned into Jayson Tatum and Jaylen Brown.
This 2007 trade wasn't all that great on the Timberwolves' end, either, meaning the Celtics really did win both of their trades centered around Garnett. Kevin Garnett WAS the Timberwolves. He was their first true superstar and an MVP winner with the team. He even led the only Timberwolves team to win a playoff series until Minnesota did again that during the 2023-24 season.
While the seven-for-one player deal constitutes the most players traded for one player ever, none of the players Minnesota got back contributed close to what Garnett provided the team. Every player involved other than Al Jefferson was just a role player, and Jefferson was only a fringe All-Star talent. While his best years came with the Timberwolves, he left the team after only three seasons, too.
Garnett, meanwhile brought his elite defense and fierce competitive mindset to Boston en route to winning a championship with the team. The big four he formed with Pierce, Ray Allen, and Rajon Rondo became one of the most legendary squads of the 21st century.
2. The Chris Paul trade (2011)
ChatGPT summary:
Trade Details:
- Los Angeles Clippers receive: Chris Paul
- New Orleans Hornets receive: Eric Gordon, Al-Farouq Aminu, Chris Kaman, and unprotected 1st-round picks (including a 2012 pick that eventually became Austin Rivers).
Why It’s One of the Worst Trades:
Although the Clippers got an elite point guard in Chris Paul, the Hornets—at the time owned by the NBA—did not get a fair return for a top-five player. Eric Gordon showed flashes of brilliance, but injuries derailed his career, and he never became the franchise cornerstone the Hornets hoped for. Al-Farouq Aminu was a decent role player but not a star, and the picks didn’t translate into anything of consequence. Chris Kaman, at the time, was a decent big man but not nearly enough to offset the loss of Paul, who immediately propelled the Clippers into title contention. The trade marked a significant misstep in rebuilding the Hornets.
ClutchPoints analysis:
The Chris Paul trade scandal is one of the most infamous moments in NBA history. The Hornets were owned by the NBA at the time, and Commissioner David Stern nullified a trade that would have sent Paul to the Lakers. The commissioner stated that the Hornets were not getting enough back for such an elite point guard.
There is an argument to be made that the Hornets would have received more from the Lakers than they did in the eventually agreed-upon deal with the Clippers. Paul was an MVP candidate at this time, yet the Hornets only netted three role players and one first-round pick for him.
Paul joined the Clippers and became the maestro that led Lob City, one of the most exciting teams in NBA history, due to the frequency in which they connected on highlight reel alley-oops.
3. The Kobe Bryant trade (1996)
ChatGPT summary:
Trade Details:
- Los Angeles Lakers receive: Kobe Bryant
- Charlotte Hornets receive: Vlade Divac
Why It’s One of the Worst Trades:
This one might be the most famous “what could have been” trade in NBA history. The Hornets traded away Kobe Bryant—who would go on to become one of the greatest players in NBA history—just hours after drafting him. The rationale for the trade was that the Hornets needed a proven center (Divac) and were not willing to take a chance on Bryant’s potential.
However, the Lakers recognized his immense upside and seized the opportunity. Bryant went on to win five championships and became the face of the Lakers for two decades. In contrast, Divac’s best years were already behind him by the time he joined the Hornets. It’s one of the most glaring “misses” in NBA trade history.
ClutchPoints analysis:
You never truly know how draft day trades are going to pan out. Unfortunately for the Charlotte Hornets, their 1996 trade for Vlade Divac was a clear mistake. Divac was a solid player, but the draftee they traded away ended up becoming one of the best players in NBA history.
That was, of course, Kobe Bryant, the best shooting guard ever not named Michael Jordan. In fact, Bryant is the closest thing we've had to the G.O.A.T. His elite mid-range jump shot and explosive dunking led to him winning two scoring titles, but he held it down on the less glamorous side of the court, too, as he made nine All-Defensive First Teams en route to becoming one of the best defensive players ever.
Bryant won five championships, three of which were with Shaquille O'Neal, and two of which were with him as the Lakers' top dog. Bryant never left the Lakers team that added him on draft day, so it is possible the Hornets could have 20 seasons of greatness had they not traded for Divac. When we at ClutchPoints made our own ranking of the worst NBA trades ever, this deal came in at number one.
4. The James Harden trade (2013)
ChatGPT summary:
Trade Details:
- Houston Rockets receive: James Harden, Cole Aldrich, Daequan Cook, and Lazar Hayward
- Oklahoma City Thunder receive: Kevin Martin, Jeremy Lamb, two first-round picks, and a second-round pick.
Why It’s One of the Worst Trades:
The Thunder had a supernova of young talent in Harden, Kevin Durant, and Russell Westbrook, and had just made it to the NBA Finals. But the franchise, unable or unwilling to pay the luxury tax, dealt Harden away to Houston for a decent return, but nothing close to his true value.
Harden quickly became a perennial MVP candidate and led the Rockets as their franchise player. The Thunder, meanwhile, never reached the same heights again and lost out on what could’ve been a dynasty. Even though they acquired solid pieces like Lamb and picks, those didn’t come close to matching Harden's long-term impact.
ClutchPoints analysis:
James Harden trades are nothing new these days. His first trade ever, though, wasn't his own fault. It also ended up becoming a huge mistake for the Oklahoma City Thunder. Harden went from a young and exciting sixth man to a perennial MVP candidate when he joined the Houston Rockets.
The Thunder didn't see Harden becoming the league's best scorer coming, as they prioritized keeping the shot-blocking Serge Ibaka over him. If Harden had remained a member of the Thunder organization with Kevin Durant and Russell Westbrook, the sky was the limit for what the team could have accomplished. The Thunder missed out on a potential dynasty because they prioritized finances.
5. The Dwight Howard trade (2012)
ChatGPT summary:
Trade Details:
- Los Angeles Lakers receive: Dwight Howard
- Orlando Magic receive: Andrew Bynum, Jason Richardson, and picks (including a future first-rounder).
Why It’s One of the Worst Trades:
This trade was seen as the Lakers trying to load up on superstars with the hope of another championship run with Kobe Bryant, Dwight Howard, and Steve Nash. However, Dwight Howard—who was one of the top centers in the league—struggled with injuries and chemistry issues in Los Angeles.
He never regained the dominant form he showed in Orlando. Meanwhile, the Magic got Andrew Bynum, a once-promising center who never played a game for Orlando due to injury concerns, and they also didn’t receive the immediate return in the draft that they had hoped for. The Lakers gambled heavily and lost, while the Magic entered a long rebuilding phase.
ClutchPoints analysis:
ChatGPT was a little bit off on the details of this trade. Dwight Howard, Chris Duhon, and Earl Clark ended up on the Lakers, while Andrew Bynum and Jason Richardson went to the Philadelphia 76ers. The Orlando Magic ended up with Al Harrington, Arron Afflalo, Josh McRoberts, Christian Eyenga, Mo Harkless, Nikola Vucevic, a second-round pick, and three first-round picks. The Denver Nuggets were also involved and added Andre Iguodala.
The trade was obviously centered around Howard, and most of the teams involved in this trade ended up losing the deal. Bynum never lived up to his potential, Howard dealt with injuries and chemistry issues in Los Angeles, and Iguodala had a controversial ending in Denver.
The one team that did decent in this trade was the Magic. They hauled in a surplus of picks and young players. None of them were as good as Howard, but Vucevic was a pretty good replacement at the center position.
6. The Ray Allen trade (2007)
ChatGPT summary:
Trade Details:
- Boston Celtics receive: Ray Allen, Glen Davis, second-round pick
- Seattle SuperSonics receive: Wally Szczerbiak, Delonte West, and the 5th pick in 2007 (which became Jeff Green).
Why It’s One of the Worst Trades:
This trade might have worked out for the Celtics, who immediately won a championship in 2008, but for the other teams involved, it was a disaster. The Minnesota Timberwolves and Seattle SuperSonics each gave up future Hall of Famers for a collection of players who did not lead to long-term success. Al Jefferson and Jeff Green had decent careers but were never franchise players like Garnett and Allen. The Timberwolves, in particular, took a huge step back after losing Garnett, while the Sonics (who would soon relocate to Oklahoma City) failed to make the most of the picks or players they acquired.
ClutchPoints analysis:
ChatGPT got a little bit confused in their analysis and included aspects from the aforementioned Kevin Garnett trade here. That trade and the Ray Allen deal go hand-in-hand, though, as they both resulted in the Celtics becoming a superteam. While Garnett brought the intensity, Allen brought the shooting.
He is one of the best three-point shooters ever, and that skill set was vital during Boston's run at the top of the Eastern Conference during this era. The Seattle SuperSonics received a shooter in return in Wally Szczerbiak, but he wasn't nearly the caliber of player that Allen was. Jeff Green ended up having a long and productive career (that is still going), but most of his success came outside of Seattle. This trade wasn't as bad for the SuperSonics as the Garnett trade was for the Timberwolves, but it was still far from ideal.
7. The Carmelo Anthony trade (2011)
ChatGPT summary:
Trade Details:
- New York Knicks receive: Carmelo Anthony, Chauncey Billups, Anthony Carter, Shelden Williams, and a 2014 2nd-round pick
- Denver Nuggets receive: Wilson Chandler, Raymond Felton, Danilo Gallinari, Timofey Mozgov, 2014 first-round pick, 2012 second-round pick, 2013 first-round pick (unprotected).
Why It’s One of the Worst Trades:
The Knicks gave up a large number of future assets for Carmelo Anthony, expecting him to be the player who could lead them back to relevance. While Melo was undoubtedly talented, his time in New York was marred by inconsistency and a lack of playoff success.
The Nuggets, on the other hand, not only got a solid return of young players but also picked up several first-round picks that they used to build a deep, competitive roster. The Knicks effectively mortgaged their future for a player who could never deliver the championship they were hoping for, while the Nuggets rebuilt into a competitive team without sacrificing much.
ClutchPoints analysis:
ChatGPT interestingly enough claims that the Carmelo Anthony trade was a bad deal for the New York Knicks. While Anthony never did win a ring with the team, that seems a little bit unfair. After all, Anthony became a top-10 all-time NBA scorer and had a lot of big moments with the Knicks.
The Nuggets did receive a lot of good players, but none of them were great. Their hand was forced into trading Anthony, and the haul they received was decent, but I think it is also fair to say they got the worst end of this trade. Either way, this probably wasn't a horrible deal for either side involved.
