Fixing Every NBA Team's Worst Trade of the Past Decade

Zach Buckley@@ZachBuckleyNBANational NBA Featured ColumnistAugust 31, 2020

Fixing Every NBA Team's Worst Trade of the Past Decade

0 of 30

    Bruce Kluckhohn/Associated Press

    The NBA trade market is active enough that every club has a misstep on history's transaction log.

    Actually, you don't even need to travel that far back to find one. In the last decade alone, each team has at least one trade it would desperately like to have back.

    We're here to help. Whether it's preventing them from ever happening or reworking the pieces involved, we're ready to fix the worst trade each team has executed since 2010.

Atlanta Hawks

1 of 30

    John Amis/Associated Press

    The Trade: Devonte' Graham to Charlotte Hornets for two second-round picks (June 2018)

    Atlanta's miscalculation here is either doubting Graham's potential or underselling the importance of a backup point guard (or both). Either way, the Hawks let go of what turned out to be a legitimate asset for a pick it sold for cash (eventually used on Bol Bol) and a second-rounder it won't collect until 2023.

    This deal didn't need to happen. The simplest fix would just be to erase it.

    This was the 34th overall selection, and Atlanta turned it into a less attractive pick—the Hornets won 36 games the previous season and still had Kemba Walker—and another so far into the future the timeline alone doesn't give it a great chance to help the current nucleus (never mind the low percentage it even connects on a rotation player).

    Now, Atlanta may not have selected Graham (who would've scratched the outstanding itch for a shot creator behind Trae Young), but that wasn't the only opportunity to extract value. Mitchell Robinson, Gary Trent Jr., Bruce Brown and De'Anthony Melton were among the players left on the board, and each could have addressed a need with the Hawks' young core.

Boston Celtics

2 of 30

    Elise Amendola/Associated Press

    The Trade: Kendrick Perkins and Nate Robinson to Oklahoma City Thunder for Jeff Green, Nenad Krstic and 2012 first-round pick (Feb. 2011)

    The motivations for moving Perkins made sense. He was coming off a torn ACL and in need of a new contract the Celtics weren't going to pay. That gave Boston an easy out, and even the big fella deemed it a sensible swap.

    But the emotional impact of Perkins' departure shook the Celtics to their core. Kevin Garnett said, "It feels like we lost a family member today," via NBC Sports Boston's Chris Forsberg, and the Shamrocks played like it. They went just 15-12 the rest of the way and bowed out of the second round.

    The business of basketball can be brutally cold, and from a business standpoint, general manager Danny Ainge probably did nothing wrong in this deal. However, the damage done to the club's chemistry was far greater than the return package.

    Krstic couldn't replace Perkins' impact and was out of the NBA after the season. Green averaged less than 20 minutes in the 2011 postseason. The draft pick belonged to a top-tier team.

    Tinkering with a championship core is always risky, so the return better be obviously worth it. This wasn't. Ainge should've placed a higher priority on the present as Boston recovered to make a conference finals appearance the next season. If there wasn't a better win-now offer on the table, the Celtics should've played it out with Perkins, pushed with all their might in the 2011 playoffs and let him walk in free agency.

Brooklyn Nets

3 of 30

    Frank Franklin II/Associated Press

    The Trade: Gerald Wallace, Keith Bogans, MarShon Brooks, Kris Humphries, Kris Joseph, three first-round picks and a first-round pick swap to Boston Celtics for Kevin Garnett, Paul Pierce, Jason Terry and D.J. White (July 2013)

    For reasons only known to those inside the organization, the Nets thought they were a missing piece or two away from the championship in 2013. This all seemingly stemmed from a 49-win performance the previous season, which was immediately followed by a first-round exit.

    Then-owner Mikhail Prokhorov was uber-eager to try winning big and nudged then-general manager Billy King to throw caution to the wind. Brooklyn certainly did that.

    The hindsight analysis is to scrap this whole swap, but if it had to happen, there's no way the Nets needed to part with this many draft assets. The Celtics were more than ready for their demolition. Head coach Doc Rivers was already gone, and the club was clearly on the decline following a 41-win campaign.

    Brooklyn had more leverage than this trade makes you think. Pierce and Garnett were on the wrong side of 35 and only "stars" by name recognition and salary at that point. Two picks might've been enough to get this done, but had the Nets saved even just one (or axed the pick swap), they could've had a bridge to Jaylen Brown, Jayson Tatum or Collin Sexton.

Charlotte Hornets

4 of 30

    Nell Redmond/Associated Press

    The Trade: Tyson Chandler and Alexis Ajinca to Dallas Mavericks for Matt Carroll, Erick Dampier, Eduardo Najera and cash (July 2010)

    Deciding that financial flexibility was more valuable than keeping Chandler wasn't the worst move the then-Bobcats could've made. He was coming off an injury-plagued season and "couldn't coexist" with then-head coach Larry Brown, as Rick Bonnell reported for the Charlotte Observer. Dampier brought a $13 million non-guaranteed contract to Buzz City, and that was the primary incentive for the Bobcats to do this deal.

    "You have to consider that contract is probably one of the most valuable contracts in the league," then-general manager Rod Higgins told reporters. "The flexibility is the beautiful part of having Erick's deal, maybe not so much for Erick himself as a player, but for the franchise itself."

    Sounds reasonable enough, right?

    Well, Charlotte never used that flexibility for anything. Dampier wasn't repackaged in a separate deal or waived to add an impact free agent. His contract was quietly discarded in September so the Bobcats could duck under the luxury tax.

    Chandler was too good to simply dump for a get-out-of-the-tax-free card. He helped Dallas win the 2011 title, scored a $58 million deal the following summer and was 2011-12's Defensive Player of the Year. The Bobcats letting him go without bringing back a first-round pick or a well-regarded prospect was criminal roster mismanagement.

Chicago Bulls

5 of 30

    Sue Ogrocki/Associated Press

    The Trade: Taj Gibson, Doug McDermott, 2018 second-round pick to Oklahoma City Thunder for Joffrey Lauvergne, Anthony Morrow and Cameron Payne (Feb. 2017)

    The good news for Chicago is there's only so much damage a deal can do when its primary players involved are Taj Gibson, Doug McDermott and Cameron Payne. Saying that, how did the Bulls justify giving up the two best players in this deal and sending out a pick? Adding insult to insult, let's not forget less than three years earlier, the Bulls made a draft-night deal for McDermott that cost them Gary Harris and Jusuf Nurkic.

    Chicago failed on two measures in this exchange.

    The first is the draft pick. It's hard to imagine OKC would have walked away without it and feels more like Chicago failing to protect an asset. The second is overrating Payne and thinking the Bulls could bring out whatever it was that made him the 14th pick in 2015. There was zero evidence he offered legitimate upside; he was averaging 5.3 points on 33.1 percent shooting at the time of the trade.

    At the absolute least, the second-round pick needed to come out of this deal or a more enticing prospect than Payne should have been added to it. But if Gibson and McDermott couldn't fetch that package on their own, the Bulls should have attached them to a bigger swap involving Jimmy Butler or Nikola Mirotic, who weren't moved at this deadline but were both traded within 12 months of it.

Cleveland Cavaliers

6 of 30

    Jim Mone/Associated Press

    The Trade: Kyrie Irving to Boston Celtics for Jae Crowder, Isaiah Thomas, Ante Zizic, 2018 first-round pick and 2020 second-round pick (Aug. 2017)

    Irving was a 25-year-old four-time All-Star who had already delivered an NBA Finals series-clincher at the time of this trade. The Cavaliers should've been able to name their price. One rumored offer came courtesy of the Milwaukee Bucks and involved Khris Middleton, Malcolm Brogdon and a first-round pick, per Arizona Sports 98.7 FM's John Gambadoro.

    If that sounds more interesting than what Cleveland actually received (it definitely does), just wait for the next one. Before David Griffin stepped down as the Cavaliers general manager, he explored a three-team deal that would have delivered Paul George and Eric Bledsoe to Cleveland, per ESPN's Jackie MacMullan. Those are championship-level reinforcements and maybe reasons for LeBron James to consider staying rather than bolting in 2018 free agency.

    Instead, the Cavaliers settled on this package, highlighted by a 2018 pick that couldn't help James' final championship quest (and was later used on Collin Sexton) and an injury-riddled version of Thomas (who Cleveland knew was injured). James was reportedly furious about how this all went down, ESPN's Brian Windhorst said on The Lowe Post podcast (h/t Yahoo Sports' Ben Rohrbach):

    "I'm just telling you LeBron is there, and he's like, 'We could've had Eric Bledsoe and Paul George, and instead we have a draft pick who I'm never going to meet—well, I don't know about that, but I'm not meeting him this year—and we have Isaiah Thomas who is very clearly hampered and we have Jae Crowder, who's having the worst year of his career.'"

    If the Cavs could've added George and Bledsoe, that would have been a no-brainer solution. If not, they could've constructed a sturdier foundation with Milwaukee's offer.

Dallas Mavericks

7 of 30

    LM Otero/Associated Press

    The Trade: Jae Crowder, Jameer Nelson, Brandan Wright, 2016 first-round pick and 2016 second-round pick to Boston Celtics for Rajon Rondo and Dwight Powell (Dec. 2014)

    Some swaps can't be fixed. This is one of them.

    It never should have happened. The Mavs were seeking a needle-mover for the twilight of Dirk Nowitzki's career and somehow decided Rondo could be that player even though his ball dominance and shooting limitations were atrocious fits for head coach Rick Carlisle's flow offense.

    "Going back in time, it's a deal that had red flags," Carlisle said, per ESPN's Tim MacMahon. "We should have stayed away from it."

    The Mavs could have motored forward with the roster they had, or, if they were desperate to deal, targeted someone who was a clearer fit in Carlisle's system—even if it wouldn't have been as splashy an acquisition. If they had their hearts set on Rondo, they should have worked to keep at least one pick out of this trade. His tenure with the Celtics had clearly run its course, and all parties seemed ready for a change.

Denver Nuggets

8 of 30

    Frank Franklin II/Associated Press

    The Trade: Donovan Mitchell to Utah Jazz for Trey Lyles and Tyler Lydon (June 2017)

    Had the Nuggets held on to the 13th overall pick, they probably wouldn't have spent it on Mitchell. Their perimeter collection was overloaded with Jamal Murray, Gary Harris, Will Barton, Emmanuel Mudiay and Malik Beasley, though with the benefit of hindsight, Mitchell landed a tier (or more) above that entire group.

    Credit Denver for recognizing that the best player available didn't fit its needs, but this isn't enough to sacrifice a lottery pick. The fact the Jazz needed a versatile forward and still thought Lyles wasn't the answer two years after taking him 12th overall should've sounded alarms for the Nuggets. If nothing else, it signaled he wasn't enough of a sweetener to move down 11 spots on the draft board.

    The Miami Heat, who drafted 14th, were fans of Mitchell, per the Miami Herald's Barry Jackson. The Chicago Bulls, who drafted 16th and needed a playmaker, were impressed with his workout, per Yahoo Sports' Vincent Goodwill.

    Mitchell had enough buzz for Denver to demand something better than this: either a more intriguing prospect, a higher draft pick or both. If neither was available, the Nuggets could've selected him as the best prospect on the board and sorted out the rest of the roster later.

Detroit Pistons

9 of 30

    Paul Sancya/Associated Press

    The Trade: Khris Middleton, Brandon Knight and Viacheslav Kravtsov to Milwaukee Bucks for Brandon Jennings (July 2013)

    This was ostensibly the Knight-for-Jennings swap until Middleton emerged as an All-Star and taught everyone a valuable lesson about sacrificing a sweetener. Detroit clearly didn't see that kind of potential in him, though it liked him enough it was reluctant to include him in the trade, per ESPN's Zach Lowe.

    The Pistons would've done themselves a thousand favors by using Kyle Singler as a sweetener instead. There's no guarantee the Bucks would've gone for that, but Singler was a fellow rising sophomore, and his numbers looked a lot better than Middleton's.

    If Detroit liked both Middleton and Singler, it could have swapped in a draft pick instead. The Pistons knew what they had in those two and presumably valued both (Singler started 74 games and averaged 28.0 minutes in 2012-13). Deciding the pair was more important than what they could've gotten with a future second-rounder might've framed this deal differently.

    Swap Middleton out for an anonymous throw-in and maybe we remember this trade as we really should: the time two Central Division rivals swapped scoring point guards named Brandon.

Golden State Warriors

10 of 30

    Ben Margot/Associated Press

    The Trade: Andre Roberson to Oklahoma City Thunder for Archie Goodwin and cash (June 2013)

    The Warriors entered the 2013 draft without a pick. Three trades later, they had Nemanja Nedovic, or "the European Derrick Rose."

    Had they simply stopped after one transaction, they would have walked away with suffocating-stopper-in-training Andre Roberson. Putting him in the same defense as Draymond Green, Andre Iguodala and Klay Thompson would've been a cheat code come to life.

    If fate forced Golden State to the 30th pick, surely it could've done better than Nedovic, whose NBA career spanned 24 games over little more than a calendar year. Flame-thrower Allen Crabbe was still on the board. So was two-way swingman James Ennis III and stretch big Mike Muscala.

    These aren't cornerstones, obviously, but they would have cushioned the blow of giving away Roberson.

Houston Rockets

11 of 30

    Bob Levey/Associated Press

    The Trade: Kyle Lowry to Toronto Raptors for Gary Forbes and 2013 first-round pick (July 2012)

    Give Houston the benefit of hindsight and it would've laughed Toronto off the phone for this offer.

    Lowry became a six-time (and counting) All-Star after this exchange, while Forbes was out of Houston (and the NBA) before the 2012-13 season started. At least the Rockets were able to use the pick (which became Steven Adams) in the James Harden deal.

    Even still, this was someone who sets an organizational identity for a late lottery pick. The Rockets needed to squeeze more out of the Raptors.

    Toronto was looking to accelerate its rebuild—it would trade for Rudy Gay the following January—and may have been more willing to part with future assets for Lowry. Give Houston more draft considerations or an intriguing prospect like Terrence Ross and maybe history doesn't remember this deal as legalized larceny.

Indiana Pacers

12 of 30

    Eric Gay/Associated Press

    The Trade: Kawhi Leonard, Davis Bertans and Erazem Lorbek to San Antonio Spurs Spurs for George Hill (June 2011)

    As much as Indiana wanted Hill—and he did fit the franchise's puzzle almost perfectly—the Pacers' spidey sense almost tingled in time for them to walk away. They had been discussing Hill with San Antonio all night, but when Leonard was still on the board as they came on the clock at No. 15, the Pacers almost saved themselves.

    "When Kawhi ended up being there, we had to think about taking him," former Pacers general manager David Morway told Zach Lowe for a 2013 Grantland article.

    Indiana had the simple fix in its hand. Had it trusted that intuition, maybe Leonard and Paul George would have a dynasty going in the Circle City right now.

    The two found each other in L.A. this past summer, but they are racing against the clock to utilize what's left of their primes. Had the Pacers followed drafting George in 2010 with getting Leonard a year later, they would have had superteam potential with an extended window.

Los Angeles Clippers

13 of 30

    Ron Schwane/Associated Press

    The Trade: Baron Davis and 2011 first-round pick to Los Angeles Cavaliers for Mo Williams and Jamario Moon (Feb. 2011)

    The Clippers were scouring for a dumping ground to unload the roughly $30 million left on Davis' contract. The Cavaliers offered to stomach the bloated salary, but only for a first-round pick then-general manager Chris Grant insisted must be unprotected, per Terry Pluto of the Plain Dealer.

    That should have been the Clippers' cue to walk away. They weren't the worst team in the NBA, but with a 21-37 record at the time of the exchange, they were clearly headed for the lottery. There are very few instances in which a lottery-bound team can justify parting with an unprotected pick. A salary dump is not at all one of them.

    The basketball gods got to work sending L.A. a karmic message about devaluing assets and helped Cleveland strike lottery gold with this pick. The Cavaliers spent it on Kyrie Irving, who grew to become an annual All-Star and clinch their first championship with the biggest shot in NBA history.

    Putting literally any protection on this pick could've saved the Clippers' rear. It was not a good group of lottery prospects—Derrick Williams was the second pick, Jan Vesely went sixth—so L.A. could've stomached any other blow on draft night. But losing Irving (who could've formed a wildly intriguing young core with Blake Griffin and DeAndre Jordan) for financial relief is an all-time faceplant.

Los Angeles Lakers

14 of 30

    Nathan Denette/Associated Press

    The Trade: Two future first-round picks and two future second-round picks to Phoenix Suns for Steve Nash (July 2012)

    The Lakers wanted to make one last push before Father Time got the best of a 34-year-old Kobe Bryant. But when they pushed their chips to the center of the table, they did so for a 38-year-old Nash. He hadn't shown signs of wearing down just yet—he was an All-Star and averaged 12.5 points with 10.7 assists the previous season—but his age alone meant L.A. was playing with fire.

    It got burned almost immediately.

    Nash broke his leg during his second game as a Laker, and injuries would define his two-plus-year tenure with the team. He only suited up for 65 regular-season games before retiring in March 2015.

    Injuries can be unpredictable, but a 38-year-old physically breaking down hardly qualifies as shocking. That begs the question: Did the Lakers really have to move all those picks to broker a sign-and-trade?

    While three never amounted to much, the fourth was spent on Mikal Bridges, who's emerging as an ace three-and-D wing (exactly what the current Lakers need) for the Suns. Parting with two first-rounders is too much for any 38-year-old, even one with Nash's pedigree.

Memphis Grizzlies

15 of 30

    Rich Pedroncelli/Associated Press

    The Trade: Tayshaun Prince and future first-round pick to Boston Celtics and Quincy Pondexter and 2015 second-round pick to New Orleans Pelicans for Jeff Green and Russ Smith (Jan. 2015)

    The grit-and-grind Grizzlies felt they were one wing away from a lengthy playoff run in 2015, so they decided parting with a future pick was a worthy sacrifice. It may well have been had Memphis found someone more interesting than Green, who had never posted an above-average player efficiency rating.

    He wasn't the only player on the Grizzlies' radar. They also made a pitch for Luol Deng, Marc Stein reported for ESPN, but the Miami Heat weren't ready to move him. Still, Memphis had time to wait before the trade deadline to see if the Heat (16-21 at the time of this trade) would change their tune.

    Deng's defense-first approach could have been a cleaner fit for the Grizzlies. Green was a disaster in the 2015 playoffs, shooting just 33.3 percent from the field and 22.2 percent from three across 11 outings. Memphis then traded him away at the 2016 deadline.

    The Celtics, meanwhile, will finally receive their pick (14th overall) this offseason.

Miami Heat

16 of 30

    Nell Redmond/Associated Press

    The Trade: Danny Granger and two first-round picks to Phoenix Suns and Norris Cole, Justin Hamilton and Shawne Williams to New Orleans Pelicans for Goran Dragic and Zoran Dragic (Feb. 2015)

    Dragic has worn many different labels over his 12-year NBA career: underrated, All-Star, All-NBA third-teamer. Here's one that probably never entered the minds of those living outside Miami: worth two first-round picks, including one that was unprotected.

    It made sense to Heat president Pat Riley, who saw this deal as "another step in getting the Miami Heat back to real championship prominence." To everyone else, it seemed especially risky.

    "There's a long history ... of NBA teams making costly mistakes by not worrying about a seemingly distant future," ESPN's Kevin Pelton noted at the time.

    The Suns later turned the picks into Mikal Bridges. The Philadelphia 76ers flipped the unprotected 2021 first-rounder in the Tobias Harris trade. The Los Angeles Clippers later used it to help acquire Paul George.

    If the Heat couldn't do this deal with only one of the picks (attached to some level of protection), then walking away was the right call. Dragic is a helpful player to have, but he's not good enough to mortgage this much of your future.

Milwaukee Bucks

17 of 30

    John Raoux/Associated Press

    The Trade: Tobias Harris, Doron Lamb, Beno Udrih and cash to Orlando Magic for JJ Redick, Ish Smith and Gustavo Ayon (Feb. 2013)

    Patience could have saved Milwaukee from making this mess.

    Why were the Bucks scrambling to bulk up a team that was 26-27 at the time of this trade? And why did they ever think Redick's catch-and-shoot game would be a fit with the ball-dominant backcourt of Monta Ellis and Brandon Jennings?

    This whole debacle cost them a shot at developing Harris, who they traded to get during the 2011 draft and was already showing promise as a 20-year-old when this deal went down. Oh, and Redick took the first flight out of town in 2013 free agency.

    Milwaukee should have been selling win-now pieces, not chasing them. If the Bucks insisted on chasing established players and dealing prospects to get them, they needed a bigger wing who could defend his position and create his own shot. Redick checked none of those boxes.

Minnesota Timberwolves

18 of 30

    Matt Rourke/Associated Press

    The Trade: Jimmy Butler and Justin Patton to 76ers for Robert Covington, Dario Saric, Jerryd Bayless and 2022 second-round pick (Nov. 2018)

    Butler's exit from the Gopher State was imminent long before the scrimmage heard 'round the world. He said he'd been asking for a way out all summer during an appearance on The JJ Redick Podcast, but then-coach Tom Thibodeau didn't want to hear it.

    "That was the disconnect," Butler said. "That was one of the hardest things I had to do. ... To tell my guy, to tell Thibs, like, 'Hey, this ain't it.'"

    By the time the Timberwolves got around to trading Butler, they had torpedoed their leverage. Complicating matters, Minnesota prioritized instant-impact offers over future-focused packages. That's how Butler, a top two-way player, was transformed into the complementary duo of Covington and Saric, a washed-up Bayless and a future second-rounder.

    There were more interesting offers available. Houston put four first-rounders on the table, per ESPN's Adrian Wojnarowski. Miami made several pitches, one including Goran Dragic, Justise Winslow and a draft pick, another featuring Josh Richardson and a first-round pick, per The Athletic's Jon Krawczynski and Shams Charania.

    Minnesota trading Butler away without getting a first-round pick might meet the legal standard for gross negligence, especially since so much of the win-now motivation seemed tied to Thibodeau, who was fired two months after this trade. If nothing else, the Wolves should have at least brightened their present and future with one of the Heat offers.

New Orleans Pelicans

19 of 30

    Gerald Herbert/Associated Press

    The Trade: Chris Paul, 2015 second-round pick and cash to Los Angeles Clippers for Eric Gordon, Chris Kaman, Al-Farouq Aminu and 2012 first-round pick (Dec. 2011)

    When an All-Star wants out, teams can ask for and receive a king's ransom. Last summer, the Pels turned a disgruntled Anthony Davis into Brandon Ingram, Lonzo Ball, Josh Hart, De'Andre Hunter (flipped for additional prospects and a future first), two first-round picks and a first-round pick swap. When Paul George wanted out of OKC, the Thunder brought back Shai Gilgeous-Alexander, Danilo Gallinari, five first-round picks and two pick swaps.

    Paul's price tag belonged in that range. He was 26 years old and already a: four-time All-Star, three-time steals leader and two-time distributing champ. He had already proved to be a transformational talent—New Orleans lost 64 games the season before he arrived and won 56 in his third year there—and established himself as an elite.

    New Orleans needed a lot more than this. At least one more first-round pick should've headed to New Orleans, along with another high-ceiling prospect like Eric Bledsoe or DeAndre Jordan. That package still would have fallen short of Paul's value, but at least it would have been in the same zip code.

New York Knicks

20 of 30

    Michael Conroy/Associated Press

    The Trade: Marcus Camby, Steve Novak, Quentin Richardson, 2016 first-round pick and two second-round picks to Toronto Raptors for Andrea Bargnani (July 2013)

    There were two letter-grade options when this deal went down: LOL or #Knicks. It's tough to tell what New York was even attempting to do here. Forget that Bargnani had already proved he was clearly overdrafted as the No. 1 pick in 2006, he was coming off a two-season stretch in which he averaged just 15.8 points on 41.6/30.3/86.4 shooting and 4.5 rebounds across 66 games.

    Oh, and he was owed $23 million for the next two seasons with very little evidence he was capable of playing up to that pay rate. Again, it's hard to see what the Knicks even wanted in him, let alone why they felt it was necessary to give up real assets to bring him south of the border.

    The only way this would've made any sense for the Knicks is if they were collecting draft considerations to take on Bargnani's salary. The Raptors, who had just given Masai Ujiri front office control that May, might've been eager for a fresh start and ready to distance themselves from their draft-night misstep.

Oklahoma City Thunder

21 of 30

    Henny Ray Abrams/Associated Press

    The Trade: Jeremy Lamb, Kevin Martin, two first-round picks and 2013 second-round pick to Houston Rockets for James Harden, Cole Aldrich, Daequan Cook and Lazar Hayward (Oct. 2012)

    This trade should've never happened. The Thunder were four months removed from a Finals appearance and had a future so bright that staring directly at it could cause serious eye damage.

    OKC put a four-year, $55.5 million offer on the table. Harden was eligible for and wanted $60 million, Chris Broussard reported for ESPN The Magazine. Somehow, that "gulf" was insurmountable, and the Thunder opted for a future that didn't involve Harden sharing the floor with Kevin Durant and Russell Westbrook.

    "We wanted to sign James to an extension, but at the end of the day, these situations have to work for all those involved," Thunder general manager Sam Presti said. "Our ownership group again showed their commitment to the organization with several significant offers."

    It's easy to say this from the outside, but the Thunder should've paid Harden, braced for some luxury-tax hits and soaked up all the benefits of employing the league's best young nucleus (by a mile). If ownership wouldn't have signed off on the luxury tax, OKC could've waited until the deadline or even the following summer, when he would've been a restricted free agent.

    Harden is now an MVP, a three-time scoring champ and arguably the greatest point producer of his generation. He still has Houston in the contending ranks, while OKC's only remaining asset from this deal is Steven Adams.

Orlando Magic

22 of 30

    Reinhold Matay/Associated Press

    The Trade: Victor Oladipo, Domantas Sabonis and Ersan Ilyasova to Oklahoma City for Serge Ibaka (June 2016)

    Before Oladipo and Sabonis helped OKC snag Paul George and turned Indiana into a playoff regular, they helped Orlando create an antiquated jumbo lineup that had no shot at thriving in the modern game.

    The Magic already had their frontcourt of the present and future with Aaron Gordon at the 4 and Nikola Vucevic at the 5, yet they chased size wherever they could find it that offseason. In the span of two weeks, they brokered this atrocious deal for Ibaka and then threw a four-year, $72 million at Bismack Biyombo.

    Ibaka was approaching the final season of his contract and was no longer a priority for the Thunder. This deal meant the Magic were selling painfully low on Oladipo, the No. 2 pick in 2013, and sacrificing a second asset in Sabonis, the 11th pick in 2016, for someone who didn't fit their roster.

    Nixing this deal seems most advisable in hindsight, but Orlando should've at least found a way to keep one of the two building blocks it sent out.

Philadelphia 76ers

23 of 30

    Rick Bowmer/Associated Press

    The Trade: No. 3 pick in 2017 and future first-round pick to Boston Celtics for No. 1 pick in 2017 (June 2017)

    All the postmortem reports that followed Philly's swift first-round exit all asked the same question: Where did it all go wrong?

    In one word, here. This trade is where everything went awry.

    The Sixers needed Markelle Fultz to hit as the No. 1 pick. Joel Embiid and Ben Simmons needed Fultz's perimeter punch and shot-creation. The front office needed Fultz to justify parting with a future first to climb up two spots (and away from Jayson Tatum, who might already be the third-best player in the East).

    When Fultz didn't pan out—for myriad reasons—Philly tried constructing a contender around Embiid and Simmons on the fly. Assets that had accumulated over the life of The Process were now dumped into two deals, the first for Jimmy Butler and the second for Tobias Harris. Fast-forward to the present, and Philly is saddling a roster that makes no sense and a payroll that can make your eyes bleed.

    If Philly would have never done this trade, Fultz could still fall in its lap, as Boston was set to draft Tatum No. 1, and L.A. was locked onto Lonzo Ball. If Fultz didn't make it to No. 3, the Sixers could've walked away with Ball (solid) or Tatum (star) and still had their extra first-round pick to add more young talent or help facilitate another trade.

Phoenix Suns

24 of 30

    Ross D. Franklin/Associated Press

    The Trade: Goran Dragic and 2011 first-round pick to Houston Rockets for Aaron Brooks (Feb. 2011)

    By this point, it's obvious Dragic has established himself as the superior NBA player in this swap. But an argument could've been made on his behalf even at the time of this trade.

    When the Suns shipped him out, he was a 24-year-old averaging 14.8 points and 6.3 assists per 36 minutes with a 49.2 true shooting percentage. The 26-year-old Brooks was at 17.5 points and 5.7 assists per 36 minutes with a 46.5 true shooting percentage. At best, this was a lateral move, but age and growth potential probably tipped the scales in favor of Dragic.

    So, why wasn't this a straight guard-for-guard swap? And if a draft pick did need to change hands, why was it going out of Phoenix and not coming into the desert? Either adjustment gets closer to fixing this trade, which the Suns tried to reverse by giving Dragic a four-year, $34 million deal in 2012 free agency.

Portland Trail Blazers

25 of 30

    Don Ryan/Associated Press

    The Trade: Will Barton, Victor Claver, Thomas Robinson and 2016 first-round pick to Denver Nuggets for Arron Afflalo and Alonzo Gee (Feb. 2015)

    Afflalo wasn't supposed to be the center of attention in Portland, but rather the second-team spark to complement one of basketball's best starting fives. But that plan went awry after Wesley Matthews suffered a torn Achilles less than one month later.

    Suddenly, Afflalo was tasked with being a primary piece for Portland, and it just never came together for him or the Blazers. They were 36-17 at the time of the trade, went just 15-14 the rest of the way and were bounced out of the opening round in five games. He battled a shoulder strain late in the season, which kept him out of the first two playoff games and left him a shadow of his self when he finally returned (five points on 2-of-12 shooting, minus-44 in 60 minutes).

    Afflalo quietly exited in the offseason, and the Blazers parted with every starter not named Damian Lillard.

    Maybe this can simply be chalked up to bad luck, but Portland got a bit aggressive in chasing a veteran rental. Giving up either the first-round pick or Barton would've been fine, but putting both together was an overpay. Had Barton stuck around, the Blazers could have long ago scratched itches for wing depth and secondary ball-handlers.

Sacramento Kings

26 of 30

    Winslow Townson/Associated Press

    The Trade: Carl Landry, Nik Stauskas, Jason Thompson, future first-round pick and two first-round pick swap rights to Philadelphia 76ers for Arturas Gudaitis and Luka Mitrovic (July 2015)

    Come on, Sacramento. Even for the Kangz, this was brutal.

    The names involved in the actual trade don't matter. Sacramento was in hot pursuit of cap space and deemed the need dire enough to ditch all of these draft considerations (plus Stauskas, who was only one year removed from being the No. 8 pick and still theoretically intriguing).

    If you're wondering why a non-destination franchise like the Kings coveted cap space, you're onto something. Sacramento knew it wasn't getting a top-tier target, so it set it sights on this trio: Wesley Matthews, Monta Ellis and Rajon Rondo, as Marc Stein reported for ESPN. That already puts this deal on a dumpster-fire trajectory, and it only gets worse when Matthews and Ellis never came, and Rondo only stayed for a single 49-loss season.

    The Sixers, who were in the asset-collection portion of The Process, shouldn't have needed more than the one first-round pick to facilitate the salary dump. If the Kings were destined to do this, they needed to keep the pick swaps out of the equation (one of which yielded Jayson Tatum).

San Antonio Spurs

27 of 30

    Ringo H.W. Chiu/Associated Press

    The Trade: Kawhi Leonard, Danny Green and cash to Toronto Raptors for DeMar DeRozan, Jakob Poeltl and top-20 protected 2019 first-round pick (July 2018)

    While the Spurs were surely less than thrilled about being forced to trade away Leonard—who wants to give up an in-prime, two-way superstar?—they should have sensed a major opportunity to reload the franchise.

    As ESPN reported at the time, the expected price for Leonard was "a massive package of young players and draft picks." The site theorized one such offer from the Lakers could include a combination of prospects (like Brandon Ingram, Kyle Kuzma and/or Josh Hart), future first-round picks and possibly a sign-and-traded Julius Randle.

    At least five teams were in the running for Leonard at the time of ESPN's report, and Toronto wasn't included in that group. The Spurs had options. Why they chose this package is bewildering.

    Theoretically, it may have been the one that allowed San Antonio to remain the most competitive, but the organization wasn't in position to chase a win-now offer. That point has been hammered home the two seasons since, as the Spurs were dispatched from the 2019 opening round and had their playoff streak snapped this season.

    The deal should've been anchored by multiple picks and prospects under the age of 25. If that kind of offer wasn't available in July, Gregg Popovich and Co. should've practiced patience until it was. Leonard has a reasonable argument as the best player on the planet and at least ranks among the top five. The history books will never believe this was all it took for the Raptors to get him.

Toronto Raptors

28 of 30

    Matt Slocum/Associated Press

    The Trade: Jose Calderon, Ed Davis and 2013 second-round pick to Memphis Grizzlies in three-team trade for Rudy Gay and Hamed Haddadi (Jan. 2013)

    In terms of talent, there's nothing for Toronto to fix. Gay has hovered around second- or third-option status for most of his career. Calderon and Davis were complementary types on their best days, and the second-rounder was used on the forgettable Jamaal Franklin, who played 24 games across two NBA seasons.

    But Gay's fit with the Raptors could not have been worse. There was too much overlap with DeMar DeRozan, another ball-dominant scorer with limited shooting range. Gay took touches from (and muted the impact of) Lowry, who averaged 13.5 points on 41.8/39.6/83.3 shooting before the trade and only 9.9 on 38.5/33.1/73.7 after it.

    Since the issue was fit and not value, this isn't a trade even hindsight can correct. Toronto's best option was staying away, either to patiently build with its young nucleus or to accelerate the rebuild with a wing who offered better shooting and wouldn't dominate offensive possessions.

Utah Jazz

29 of 30

    Kevin C. Cox/Associated Press

    The Trade: Thomas Bryant and Josh Hart to Los Angeles Lakers for Tony Bradley (June 2017)

    Utah brokered a pair of two-for-one trades during the 2017 draft and made out like bandits with the first, when it somehow turned Trey Lyles and Tyler Lydon into Donovan Mitchell. But the Jazz should've stopped while they were ahead.

    While they weren't exactly fleeced in this exchange, the whole deal felt unnecessary. Utah only climbed two spots (from 30 to 28) for Bradley and gave up the 42nd selection to do it. Neither the Lakers nor the Spurs (who picked 29th) went with a center, so the Jazz didn't seem in danger of losing Bradley. If they did, other good big men (like Bryant) were still on the board.

    Bryant is arguably superior to Bradley, and the Bryant-Hart combo is clearly the preferred side of the exchange. The Jazz should've stayed put, as Bradley appeared likely to get to No. 30, and they could've added another prospect at No. 42, like Dillon Brooks (45th pick) or Monte Morris (51st).

Washington Wizards

30 of 30

    Jim Mone/Associated Press

    The Trade: Kelly Oubre Jr. and Austin Rivers to Phoenix Suns for Trevor Ariza (Dec. 2018)

    Giving up a long-term asset for a short-term rental always carries some inherent risk, but it can be worth the plunge for a team that's one piece away from contending.

    The 2018-19 Wizards were not that team. They were 12-18 with the NBA's sixth-worst net rating (minus-4.0) at the time of this trade. They looked more like sellers than buyers, which made it mind-numbing for them to turn the 23-year-old Oubre and 26-year-old Rivers into the 33-year-old (and 37.9 percent shooting) Ariza.

    Washington won 43 games and was bounced out of the opening round the previous season. The Wizards were clearly trying to get ahead of the campaign getting derailed, but where was this supposed to lead? Why let go of Oubre, now a catalyst in Phoenix, for a non-needle-mover? Why not give it more than two months for the team to prove capable of being more than mediocre?

    The Suns, who were going nowhere fast with Ariza, were clearly looking for whatever they could get for the veteran. If Washington waited out the market, maybe Rivers and a second-rounder would have gotten this done—and it wouldn't look nearly so disastrous now.

                        

    All stats courtesy of NBA.com and Basketball Reference unless otherwise noted.

    Zach Buckley covers the NBA for Bleacher Report. Follow him on Twitter, @ZachBuckleyNBA.