The NBA is famously a league of transactions. Teams must nail their trades, signings and draft picks to compete for the title, and fan interest in those dealings is often higher than in the games themselves.
Some of these transactions result in meteoric success. Just look at the past two NBA champions: The Oklahoma City Thunder and Boston Celtics traded for Shai Gilgeous-Alexander, Alex Caruso, Derrick White, Jrue Holiday, Al Horford, Kristaps Porzingis and draft picks that became Jalen Williams, Jayson Tatum and Jaylen Brown. Other recent champions landed their MVPs with the No. 41 (Nikola Jokic) and No. 15 (Giannis Antetokounmpo) picks.
Yet other transactions flame out spectacularly. It's those rotten deals that we've put under the microscope.
Following ESPN colleagues who have done the same for NFL, MLB and Premier League teams, we're highlighting the worst decision every NBA team has made thus far in the 2020s, ranking them from least to most damaging.
Note that we're ranking the disastrousness of these deals in retrospect, so even moves that made sense at the time can be included here. As ESPN's Bill Barnwell wrote in his NFL ranking, "I'm evaluating the outcome. If the process was clearly bad at the time, that's a bonus, but this is measuring the severity of each wrong choice, not why something happened."
The process here is the same. Let's take a look at the most damaging moves NBA teams have made this decade.
Jump to a tier:
Tier 1: Franchise-altering trades | Tier 2: High cost, low reward
Tier 3: Midtier mistakes | Tier 4: Draft disasters
Tier 5: Small-scale problems
Tier 5: Small-scale problems
30. Cleveland Cavaliers
Biggest mistake: Declining Isaiah Hartenstein's qualifying offer (2021)
The Cavaliers haven't made many mistakes this decade while rebuilding a contender following LeBron James' second departure. They selected Evan Mobley with their top draft pick of the decade (and traded most of the rest of their first-rounders for Donovan Mitchell), constructed a strong core and locked it up with long-term deals. The franchise's last big mistake was hiring John Beilein as coach, but that was in 2019.
On a smaller scale, Cleveland surely regrets not extending Hartenstein a qualifying offer in 2021. Already a journeyman at that point, Hartenstein had been waived by the Houston Rockets and traded by the Denver Nuggets for JaVale McGee -- ironic given Denver has spent the ensuing half-decade searching in vain for a proper backup center to Jokic.
Hartenstein flashed his potential in a short stint in Cleveland, averaging 17 points, 12 rebounds and 5 assists per 36 minutes in 16 games. Yet after drafting Mobley, the Cavaliers figured they didn't need Hartenstein anymore -- only to watch him turn that potential into greater on-court production with the LA Clippers, New York Knicks and Oklahoma City Thunder, becoming a crucial contributor to an NBA champion in the process.
29. Indiana Pacers
Biggest mistake: Hiring Nate Bjorkgren as head coach (2020)
Few NBA coaching stints have gone so poorly so quickly as Bjorkgren in Indiana. A former G League coach and NBA assistant -- he won the 2019 championship with the Toronto Raptors -- Bjorkgren clashed with Indiana's veterans and lost command of the locker room. In his lone season as the Pacers' head coach, they missed the playoffs for the first time in six years.
This mistake ranks only 29th because it arguably worked out for the Pacers in the end. Because they let Bjorkgren go after just one season, they were positioned to hire a new coach in 2021 -- just in time for Rick Carlisle to step down from the Dallas job and rejoin the Pacers.
28. New York Knicks
Biggest mistake: Signing Evan Fournier for four years and $73 million (2021)
The Knicks added Fournier via a sign-and-trade on the strength of a two-year run in which he averaged 18 points per game and made 40% of his 3s. But after averaging a respectable 14 points in 80 games in his first season in New York, Fournier's game fell apart. He averaged just 6 points in 27 games in his second season and missed New York's playoff run because of an injury, then averaged 4 points in three games in his third season before moving to Detroit at the deadline.
The Knicks signed Fournier for four years, but ultimately, he was out of the NBA and playing in Europe after just three.
27. Portland Trail Blazers
Biggest mistake: Re-signing Jerami Grant for five years and $160 million (2023)
Just one day after the Trail Blazers and Grant agreed to a new contract in summer 2023, news broke that Damian Lillard had requested a trade out of Portland. All of a sudden, an expensive but understandable long-term deal looked horribly out of place, as the veteran forward no longer fit on a retooling roster.
Two years later, Grant's production has cratered -- shooting a career-worst 37% from the field last season -- and he has fallen behind the much younger Deni Avdija and Toumani Camara in Portland's perimeter pecking order.
Grant's contract hasn't gotten in the way of any other Trail Blazers moves yet -- but with the Blazers rising, Jrue Holiday's hefty deal now in the fold and Grant still owed another $102.6 million over the next three seasons, it might soon prove a tricky roster-building obstacle.
26. Utah Jazz
Biggest mistake: Not trading Lauri Markkanen (2023-24)
Three years into their rebuild following the Donovan Mitchell and Rudy Gobert trades, the Jazz are still cellar dwellers, with by far the worst roster in the Western Conference. It's unclear whether Markkanen, now 28, still makes sense in Utah, given the team's protracted timeline.
But the problem is he had much more trade value two years ago, after he broke out and won Most Improved Player, than he does now after signing a big new contract and declining from his short-lived All-Star level. Markkanen averaged 26 points per game on 50% shooting in 2022-23 but fell to 19 points on 42% shooting last season.
25. Charlotte Hornets
Biggest mistake: Signing Gordon Hayward for four years and $120 million (2020)
The Hornets aren't typically big spenders in free agency, but they made a sizable splash with a sign-and-trade in 2020. In six offseasons this decade, only two free agents have signed for more money while changing teams than Hayward: Paul George (to Philadelphia) and Fred VanVleet (to Houston).
But as Hayward's health deteriorated, he fell far short of the Hornets' expectations. The veteran wing played in just 59% of Charlotte's games while he was on the roster, and his production declined every year. Charlotte never made the playoffs with Hayward, and he was inactive for both of the Hornets' play-in games during that span.
Eventually, Charlotte traded Hayward in the final year of his contract, receiving a package headlined by Tre Mann and second-round picks.
24. LA Clippers
Biggest mistake: Never developing young perimeter talent (2020-25)
If we started this exercise a year earlier, the Clippers would rank near No. 1 on this list because of 2019's momentous trade with the Thunder, which sent Gilgeous-Alexander and a raft of picks to Oklahoma City. But in the 2020s, there's not one specific move to highlight as a big mistake from the LA front office.
Rather, the team's mistake is more general: failing to develop any young perimeter talent to support Kawhi Leonard and Paul George. (The Clippers were much more successful at center, with Ivica Zubac and one season of Hartenstein). Until the Clippers acquired James Harden, their starting backcourts in the playoffs this decade featured Reggie Jackson, Patrick Beverley, Landry Shamet, Russell Westbrook and Eric Gordon -- not exactly championship-caliber guards.
To be fair, the Clippers didn't have any prime draft picks this decade, due to the 2019 deal with Oklahoma City. But they also whiffed on the two late first-rounders they landed (Keon Johnson and Kobe Brown), and they didn't find any perimeter diamonds in the rough, either. The closest they came was with Terance Mann, a second-round pick in 2019, but after flashes of promise early in his career, he ended up being traded -- in part because of his contract -- twice in the span of a few months earlier this year.
Tier 4: Draft disasters
23. Oklahoma City Thunder
Biggest mistake: Trading four future rotation players after the draft (2020 and 2021)
Even the best general managers lose trades. Such is the case with Sam Presti, a masterful architect of a championship roster and potential dynasty, but an error-prone trader nonetheless.
Three draft deals reflect Presti's all-too-human fallibility. In 2020, he dealt the No. 25 and 28 picks for No. 17, thereby giving away future starters Immanuel Quickley and Jaden McDaniels, while bringing Aleksej Pokusevski to Oklahoma City. In 2021, he traded up from No. 36 to No. 32, reaching for Jeremiah Robinson-Earl instead of being content with useful backup Miles McBride. Worst of all, also in 2021, Presti traded No. 16 pick Alperen Sengun -- a European prospect who, unlike Pokusevski, panned out -- to Houston for two future picks, which he used a year later in a package for Ousmane Dieng.
To review, Presti traded an All-Star center, an All-Defensive wing and two quality guards for Pokusevski, Robinson-Earl and Dieng. The first two are no longer on the Thunder, and Dieng is a deep bench player. But because Presti also traded for an MVP and drafted Chet Holmgren and Jalen Williams on the same night, his team is now the best in the NBA. A few big hits can outweigh all the misses.
22. Boston Celtics
Biggest mistake: Trading Desmond Bane (2020)
This was a reasonable move at the time: The Celtics didn't have room on their roster for another young player, and trading Bane's draft rights allowed them to shed Enes Freedom's salary. Nobody expected the No. 30 pick to develop into the sort of player who'd one day command four first-round picks in a trade.
But Bane did, and Boston certainly could have used him over the past half-decade. A solid defender for his position and career 41% 3-point shooter, Bane would have been a perfect fit in the Celtics' system.
21. Houston Rockets
Biggest mistake: Drafting Jalen Green over Evan Mobley (2021)
Green is a better player than the other mistake picks discussed in this tier. But the opportunity cost for selecting him was also higher, because after the Rockets took Green with the No. 2 pick, Mobley went third.
That decision might end up rebounding to the Rockets' benefit in the end, as Green was the centerpiece of Houston's trade for Kevin Durant this summer and the Rockets landed a different All-Star big man later in the 2021 draft in Sengun. If a Durant-Sengun frontcourt leads the Rockets to the NBA Finals next year, they'll look back on the 2021 draft as a crucial team-building moment, rather than a missed opportunity.
But for now, it's hard not to wonder what the Rockets would look like with Mobley instead of Green -- especially given the team's defensive identity with Ime Udoka at head coach and Mobley's status as the reigning Defensive Player of the Year. With the possible exception of Amen Thompson, Mobley has a higher ceiling than any of the Rockets' young building blocks.
20. Orlando Magic
Biggest mistake: Drafting Jett Howard (2023)
Two seasons into his career, No. 11 pick Howard is averaging 3.8 points per game and making just 29% of his 3-point attempts. He has played 14 total minutes across two playoff series.
Howard's selection was a fiasco for the Magic for three reasons. First, he was a reach at the time (he went 20th in ESPN's final mock draft), and the gamble hasn't paid off.
Second, his stalled development is a particular problem because Orlando -- which ranked 25th in 3-point shooting the year before Howard's arrival, 24th his rookie year and 30th last season -- thought he could help correct its longtime struggles. He hasn't. And third, players picked soon after Howard include Dereck Lively II (12th), Gradey Dick (13th), Jordan Hawkins (14th) and Brandin Podziemski (19th), all of whom have contributed much more than Howard in the NBA.
19. San Antonio Spurs
Biggest mistake: Drafting Joshua Primo (2021)
San Antonio selected Primo with the 12th pick in the 2021 draft. He averaged 5.9 points per game before being waived in October 2022 after allegations of indecent exposure to a female Spurs employee.
The Spurs' other lottery picks this decade have all worked out to varying degrees: Devin Vassell (11th), Jeremy Sochan (9th), Victor Wembanyama (1st) and Stephon Castle (4th), with 2025 picks Dylan Harper (2nd) and Carter Bryant (14th) to be determined.
But the Primo pick failed on multiple levels. Wings selected shortly after Primo in the 2021 draft included Moses Moody (14th), Corey Kispert (15th), Trey Murphy III (17th) and Jalen Johnson (20th).
18. Washington Wizards
Biggest mistake: Drafting Johnny Davis (2022)
Among lottery picks from 2020 through 2023, the worst career box plus-minus (BPM) belongs to Davis, the No. 10 pick in 2022. BPM calculates that Davis has made the Wizards worse by a whopping 6.2 points per 100 possessions.
Davis' surface stats don't look any better: 3.5 points, 0.6 assists and 11.4 minutes per game with ghastly 40%/27%/56% shooting splits. Not every lottery pick pans out, but few bust as dramatically as Davis. Worst of all is who Washington missed by selecting Davis; the next guard taken in the 2022 draft, just two spots later, was Jalen Williams.
17. Golden State Warriors
Biggest mistake: Drafting James Wiseman second (2020)
In retrospect, Golden State's much ballyhooed "two timelines" plan was doomed as soon as it began. Blessed with the No. 2 pick after a gap year -- when Kevin Durant left for Brooklyn and Klay Thompson and Stephen Curry were injured -- the Warriors had the rare opportunity to add a star prospect to a contender. If their pick clicked, they could give Curry the boost he needed to return to the Finals and set the franchise up for longer-term success after Curry's eventual decline.
At least the first part worked out, though in spite of Wiseman, not because of him. The Warriors won the 2021-22 title without the young center, who missed the entire year because of a torn meniscus. Wiseman was raw, inexperienced and a defensive liability, and his injuries didn't help him learn how to play in the Warriors' unique system. The next season, Golden State dealt Wiseman for Gary Payton II, who was undrafted but a much better bet to earn Steve Kerr's trust.
In the Warriors' defense, 2020 was a strange draft affected by the COVID-19 pandemic. But in selecting Wiseman with their best pick to set up its future, Golden State passed on LaMelo Ball (who went No. 3) and Tyrese Haliburton (who went 12th). Haliburton, for his part, said he believes the Warriors would have drafted him if they had a pick lower than No. 2.
Six years later, the Warriors are stuck trying to eke out more wins while Curry is still near his peak, because there is no more succession plan in Golden State.
Tier 3: Miscellaneous midtier mistakes
16. Minnesota Timberwolves
Biggest mistake: Trading for D'Angelo Russell (2020)
To some extent, the Timberwolves' trade for Russell worked out in the long run, because they eventually dealt him for Mike Conley and Nickeil Alexander-Walker en route to back-to-back conference finals appearances. But there must have been a less expensive way to get backcourt help, because the Timberwolves first acquired Russell in exchange for Andrew Wiggins and a future first-round pick.
Wiggins became arguably the second-best player on the title-winning 2021-22 Golden State Warriors, and that draft pick landed at No. 7 and became Jonathan Kuminga.
Meanwhile, Russell never took off in Minnesota, despite his well-documented friendship with Karl-Anthony Towns, and the Timberwolves rightly realized they needed a better option at point guard if they ever wanted to win in the postseason. In his lone playoff series with Minnesota, Russell averaged 12 points per game on 33% shooting.
15. Denver Nuggets
Biggest mistake: Not trading for any new players for two years after winning the title (2023-25)
Between the Nuggets' title in 2023 and this month, when they traded Michael Porter Jr. for Cameron Johnson, they didn't add a single NBA player in a trade. (They did make a few trades involving draft picks.)
That inactivity, which was largely motivated by financial reasons and eventually cost GM Calvin Booth his job, meant Denver was stuck replacing departed veterans from within, or from the Dario Saric/Justin Holiday/Russell Westbrook bargain bin in free agency.
Those replacements were either too young or too old, and they couldn't give Nikola Jokic the support he needed to reach another Finals. In the 2022-23 postseason, Denver's starters had a plus-9.4 net rating; this spring, in the 2024-25 playoffs, it was plus-11.3. But while all other Nuggets lineups outscored their opponents by 98 points in 2022-23 thanks to contributions from the likes of Bruce Brown Jr. and Jeff Green, other Nuggets lineups in 2024-25 had a negative-142 point differential.
14. Los Angeles Lakers
Biggest mistake: Losing 3-and-D players from their championship team (2020 and 2021)
The Lakers won the 2020 championship with a simple formula: LeBron James and Anthony Davis plus 3-and-D role players equals success. But they forgot the old maxim "if it ain't broke, don't fix it" and exchanged 3-and-D wings for ball handlers in their quest to win again.
Shortly after winning the title, they traded Danny Green and a late first-round pick (which became Jaden McDaniels) for Dennis Schroder. A year later, they lowballed Alex Caruso in free agency, leading him to sign with the Chicago Bulls. And the coup de grâce came with an ill-fated blockbuster trade, as they traded Kyle Kuzma and Kentavious Caldwell-Pope for post-prime Russell Westbrook.
Each of those moves was worse than the last, with Westbrook in particular failing to fit into the Lakers' James-centric ecosystem. They missed the playoffs in Westbrook's first season with the team and traded him -- along with a future first-round pick -- midway through the second season. But the overall effects of the front office's misguided change in approach are clear: The Lakers won four playoff series in 2020, but they've won just two total playoff series in the five seasons since.
13. Detroit Pistons
Biggest mistake: Hiring Monty Williams as head coach (2023)
In four seasons with the Phoenix Suns, Williams reached the Finals, won a Coach of the Year award and won 63% of his games. He's a well-respected coach and a longtime NBA voice.
But his tenure was a disaster in Detroit, where he was hired shortly after the Suns fired him following a second-round playoff loss. Given what was, at the time, the largest coaching contract in NBA history (six years and $78.5 million), Williams didn't seem to have a grasp on his new players' strengths and weaknesses, and his rotations boggled the mind. He lambasted his players in public. His two-big lineups cramped the Pistons' spacing. He started draft bust Killian Hayes over promising sophomore Jaden Ivey.
Amid all that turmoil, Detroit lost a record 28 consecutive games and finished 14-68, the worst record in franchise history. It wasn't just a lost season but a step backward for a team in need of forward momentum. The situation became so untenable that Williams was fired after the season, despite still being owed $65 million.
If anything, Williams' tenure looks even worse in retrospect. Williams' replacement, J.B. Bickerstaff, finished second in Coach of the Year voting as he cleaned up Williams' mess, leading the Pistons back to the playoffs and helping Cade Cunningham develop into an All-NBA player.
Tier 2: Too high a cost for too little reward
12. Miami Heat
Biggest mistake: Trading for Terry Rozier (2024)
Despite his reputation for star hunting, Heat majordomo Pat Riley isn't a reckless trader. Rather, he typically pulls the trigger on only game-changing moves. To wit, over the past 15 years, the only players Miami has acquired while trading a first-round pick are LeBron James, Chris Bosh, Goran Dragic, Jimmy Butler ... and Rozier.
The first four of those players all made All-Star teams in Miami and helped lead the Heat to the Finals. Rozier, conversely, averaged 12.5 points on 40% shooting, didn't appear in a single playoff game and fell out of coach Erik Spoelstra's rotation, as well as became embroiled in a federal gambling investigation.
Making matters worse in the big picture is that Rozier represented the Heat's last big swing to give Butler another co-star, before he asked out of Miami. Now they're stuck, with no obvious path back to relevance -- and they still owe a future first-rounder to the Hornets as payment for Rozier.
11. Toronto Raptors
Biggest mistake: Repeatedly trading first-round picks for role players (2022-2025)
At each of the past four trade deadlines, the Raptors have dealt a first-round pick despite not being a playoff team in three of those years and not having home-court advantage in the fourth. Here's the list of those acquisitions:
2022: Thaddeus Young (pick landed at No. 20, Malaki Branham)
2023: Jakob Poeltl (pick landed at No. 8, Rob Dillingham)
2024: Ochai Agbaji and Kelly Olynyk (pick landed at No. 29, Isaiah Collier)
2025: Brandon Ingram (pick belongs to Pacers in 2026)
It's not as if those picks have landed any can't-miss prospects, but the opportunity cost for Toronto is steep. And none of the players the Raptors acquired has boosted them into contention. Young, who joined the Raptors for their only postseason appearance since 2020, averaged 3.3 points in 14.5 minutes per game in those playoffs.
10. Philadelphia 76ers
Biggest mistake: Committing $399 million in new money to Paul George and Joel Embiid (2024)
It's hard to blame one particular transaction for all of the 76ers' playoff failures this decade, as the franchise is still searching for its first conference finals appearance since 2001. Ben Simmons washed out. Embiid was repeatedly injured. The team lost Game 7 in the second round twice.
But at least Philadelphia was making the playoffs and contending for the first half of the decade. In 2024-25, though, the 76ers finished 24-58, their worst record since the "Process" days a decade earlier, and now their future looks as uncertain as ever. Summer 2024 -- when they were widely declared offseason winners -- is responsible.
The 76ers signed the 34-year-old George away from the Clippers for four years and $211.6 million, and they extended the injury-prone Embiid for three years and $187.6 million, even though he still had another two years and a player option on his existing contract. Then George struggled through his worst season in a decade, and Embiid played just 19 up-and-down games.
Now the 76ers have George on the books for another three years, while Embiid's newest extension doesn't kick in for another year. And neither veteran looks poised to prove last season was a fluke, as both might miss the start of the 2025-26 season because of injuries.
9. Chicago Bulls
Biggest mistake: Trading for Nikola Vucevic (2021)
The Bulls' biggest mistake this decade might be a broader one, as they've continually aimed for the middle of the standings rather than following the tank-and-rebuild cycle that most NBA teams employ when they have little hope of contention. But Chicago's malaise began with the Vucevic trade, the first of lead executive Arturas Karnisovas' tenure, which sent Wendell Carter Jr. and two future first-round picks -- both of which landed in the lottery -- to Orlando in exchange for Vucevic.
Vucevic is a solid player, a two-time All-Star who was in the midst of a career season in Orlando when he was traded. But because of his defensive difficulties, there's a firm ceiling on a team with Vucevic in the middle, so his acquisition symbolizes the Bulls' larger lack of ambition. Indeed, Chicago finished with a total of one playoff win with Vucevic, DeMar DeRozan and Zach LaVine.
Meanwhile, Orlando used the first of its extra draft picks on Franz Wagner, who would have been the best young player in Chicago since Jimmy Butler. (The second extra pick went for Jett Howard, discussed earlier as a major mistake for the Magic.)
8. Memphis Grizzlies
Biggest mistake: Trading for Marcus Smart (2023)
After consecutive seasons with 50-plus wins and the No. 2 seed, the Grizzlies sought the final player they thought could vault them over the top. They targeted Smart, a Defensive Player of the Year who played in the NBA Finals with the Celtics, and paid a heavy cost to pair him with Ja Morant in the backcourt: two first-round picks and Tyus Jones, perhaps the league's top backup point guard.
But as the rest of the Grizzlies' rotation was waylaid by injuries and suspensions, Smart was part of the problem rather than a fix. He played just 39 games in 1½ seasons with the Grizzlies before they traded him -- using a third first-round pick to dump his contract -- at the 2025 deadline. According to VORP (value over replacement player), Smart provided precisely zero value over a replacement player during his time in Memphis.
7. Atlanta Hawks
Biggest mistake: Trading for Dejounte Murray (2022)
6. New Orleans Pelicans
Biggest mistake: Trading for Dejounte Murray (2024)
First things first: It's not Murray's fault he has been the target of two of the worst trades of the decade. He's a one-time All-Star and All-Defensive honoree.
But we're grouping these two moves because of his cursed transaction tree.
First, the Hawks, seeking to find a backcourt partner for Trae Young and regain the magic that had propelled them to a surprising conference finals berth in 2021, acquired Murray from the Spurs in exchange for three future firsts and a pick swap. One of those picks (via the Hornets) didn't end up conveying, but the Spurs landed Carter Bryant (the No. 14 pick last month) from this deal, and they still control the Hawks' unprotected picks in 2026 and 2027.
Despite that high cost, Murray didn't get Atlanta anywhere closer to contention. The Hawks didn't finish with a winning record in either season that Murray was on the roster, and lineups with Young and Murray playing together were outscored both years.
Atlanta's saving grace is that New Orleans made an even more lopsided trade for Murray just two years later, nabbing the All-Star guard in exchange for Dyson Daniels and two first-round picks (one of which the Hawks dealt in the Kristaps Porzingis trade, the other set to convey in 2027).
If that deal were just a straight-up swap of Murray for Daniels, Atlanta would have won it. Murray tore an Achilles as the Pelicans finished 21-61 last season, while Daniels, who's seven years younger, won the Most Improved Player award and finished as the Defensive Player of the Year runner-up. That the Pelicans also surrendered two firsts only makes their side of the trade look worse.
Tier 1: Franchise-altering terrible trades
5. Sacramento Kings
Biggest mistake: Having Tyrese Haliburton and De'Aaron Fox, then losing them both within three years (2022 and 2025)
The Kings faced an enviable dilemma in 2022: In 24-year-old Fox and 21-year-old Haliburton, they had two promising young point guards on the roster, and they needed to decide whether to build around one or both. They chose one, and they chose wrong, with the shocking swap of Haliburton for Domantas Sabonis.
For a time, this deal seemed like it might have been a win-win, as Haliburton blossomed in the Pacers' backcourt while the Fox-Sabonis duo led the Kings to the NBA's best offense and the West's No. 3 seed in 2022-23. It was the franchise's first playoff appearance in 17 years.
But Sacramento could only light the beam for so long, and after a seven-point loss to the Pelicans, the Kings missed the playoffs in 2023-24, then traded a disgruntled Fox in 2024-25 and missed the playoffs again.
Just a couple of years after their best run in decades, the Kings once more possess an ill-fitting roster with no clear direction, and they've gone from two point guards to zero. Meanwhile, Haliburton led the Pacers to the Eastern Conference finals and Game 7 of the NBA Finals in consecutive years, becoming one of the league's best passers and clutch scorers in the process.
4. Brooklyn Nets
Biggest mistake: Trading for James Harden (2021)
There are so many what-ifs that could have flipped the Harden trade from debacle to triumph. What if Harden and Kyrie Irving hadn't been injured in the 2021 postseason? What if Kevin Durant's foot hadn't touched the 3-point line when he tied Game 7 against the Milwaukee Bucks with a turnaround jumper? What if Irving hadn't refused the COVID-19 vaccine, bringing the Nets' three-star experiment to a sudden end?
But all of those what-ifs went the wrong way, and the Harden trade did, too. In exchange for 1½ drama-filled seasons full of more hypothetical wins than actual ones, the Nets traded Jarrett Allen, Caris LeVert, three first-round picks and four swaps (two of which didn't end up exercising).
Houston has already used its bounteous return to draft Tari Eason and Reed Sheppard and to help trade for Durant from the Suns. There is more to come; in a later deal, the Nets also had to give Houston more picks to claw some of their selections back, once they realized the Durant-Harden-Irving era was over and they needed to tank.
Adding insult to injury, when Harden demanded a trade in 2022 and the Nets submitted by trading him to Philadelphia, the centerpiece of their return was Ben Simmons, who never recaptured the two-way value that made him an All-NBA honoree in 2020. Simmons averaged 16 points per game during his tenure as a 76er, versus just 6.5 points per game during scattered periods of availability with the Nets.
3. Milwaukee Bucks
Biggest mistake: Trading for Damian Lillard (2023)
Perhaps more than any other transaction on this list, the Bucks' trade for Lillard seemed smart at the time. They needed a shakeup after a shocking 8-over-1 upset loss to the Heat in the 2023 playoffs, their offense needed an upgrade, and Lillard seemed like a perfect fit next to Giannis Antetokounmpo -- who signed an extension soon after the Bucks traded Jrue Holiday (who was rerouted to Boston, where he won a title), Grayson Allen, a future first-round pick and two swaps in exchange for Lillard.
But two main issues meant the Bucks didn't just fail to compete for another title with Lillard aboard, they didn't win a single playoff series. The first issue was that even when both players were healthy, Lillard and Antetokounmpo didn't mesh as well in practice as they did in theory. The two future Hall of Famers ran only 20.2 picks per 100 possessions, per GeniusIQ, which ranked a middling 46th out of 83 pick-and-roll combinations over the past two seasons (minimum 500 total picks).
The second problem was that both players were never healthy when it mattered most (with apologies to the Bucks' NBA Cup triumph). Antetokounmpo missed all of the 2023-24 postseason, while Lillard missed parts of both the 2023-24 and 2024-25 playoffs, the latter due to an Achilles tear that ended his Bucks tenure prematurely.
Months after his injury, the Bucks made the surprising decision to waive and stretch the remainder of Lillard's contract to give them the necessary cap space to sign free agent center Myles Turner. But now the Bucks have an annual $22.5 million charge for Lillard through 2029-30, and they don't control their first-round pick until 2031.
2. Phoenix Suns
Biggest mistake: Trading for Kevin Durant and Bradley Beal (2023)
Mat Ishbia officially assumed controlling interest as Phoenix's new owner on Feb. 7, 2023. Just over 24 hours later, the Suns traded for Durant. So-called new owner syndrome had never before manifested so quickly: Ishbia pushed his team to give up a massive haul for Durant -- Mikal Bridges, Cam Johnson, Jae Crowder, four unprotected first-round picks and a swap -- setting into motion a chain of events that have all but wrecked a team that reached the NBA Finals in 2020-21 and won a league-best 64 games in 2021-22.
It wasn't just the Durant trade that was the problem; it was the Suns' insistence on doubling down again and again, mortgaging every aspect of their future for increasingly long odds of winning in the present. That summer, Phoenix traded Chris Paul for Bradley Beal, who had a no-trade clause and more than $200 million remaining on his contract.
The total cost for Durant and Beal, counting the extra picks that Brooklyn and Washington landed when they rerouted Bridges, Johnson and Paul, was 12 first-round picks and six swaps, plus by far the most expensive roster in the NBA and extraordinary punishments wrought by the second apron.
And the reward for all of that aggressive spending? A second-round playoff loss in Durant's first season, a first-round sweep in his second (Beal's first) and an 11th-place finish in the West last season.
Now Durant has been traded away for much less than what brought him to Phoenix; Beal has been bought out and stretched, and will count $19.4 million against the Suns' cap for the next half-decade; and the Suns don't control their first-round pick until 2032. No franchise in the NBA is in a worse long-term situation than Phoenix.
1. Dallas Mavericks
Biggest mistake: Trading Luka Doncic (2025)
Could any other transaction be No. 1? The most recent entry on this list is also the worst, and perhaps the most shocking, transaction in NBA history.
The other trades at the top of this list are mostly about teams trading too many assets to bring in a star. The Doncic deal, conversely, came when a team traded away a beloved incumbent star who had led that organization to the Finals the previous summer and made a record five first-team All-NBA appearances through age 24.
Because the Mavericks' post-Doncic collapse in the 2024-25 season meant they ended up in the lottery, where they miraculously lucked into the No. 1 pick and Cooper Flagg, their future looks brighter than that of the Suns, Bucks, Nets or Kings. Flagg and Anthony Davis -- the centerpiece of Dallas' return for Doncic -- could lead Dallas back to contention with speed.
But only one transaction this century was so surprising that it sparked questions about whether ESPN's Shams Charania's social media account been hacked when he reported it. Only one transaction was so absurd that it became a flashbulb memory, and fans across the world will remember, for decades to come, where they were when they learned the news. Only one transaction, most of all, was so outrageous that it sparked a mass revolt from its fan base.
That, more than anything else, is why the Doncic trade ranks No. 1: It transcended typical transaction reactions and penetrated the very heart of sports fandom. That takes a special sort of once-in-a-century mistake.