Jimmy Butler and the NBA's Messiest Superstar Breakups Since 2010
Breaking up in the NBA isn't always hard to do, but even when it's not, it sure can get messy. This is especially true for superstar divorces.
Marquee names have the leverage to create awkward and contentious situations if they deem it necessary. And because the stakes are so high for jilted teams, the separation process often delivers urgent coverage and maximum chaos.
Jimmy Butler is a perfect example of just how extreme these dissolutions can become. Not only is he fresh off a contentious exit from the Miami Heat, but his Golden State Warriors are duking it out in the Western Conference semifinals against the Minnesota Timberwolves, the team he openly forced his way off back in 2018.
Because topical nostalgia is one heck of a drug, this feels like a great time to revisit the messiest, most contentious superstar breakups in recent memory. Divorces will be presented in chronological order, and the cutoff for inclusion is 2010. Shaquille O’Neal can thank us for these ground rules later.
Now, let’s journey through the “Well, that was awkward,” wormhole.
LeBron James and the Cleveland Cavaliers (2010)
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The way LeBron James announced he would be leaving the Cleveland Cavaliers for the Miami Heat as a free agent in 2010 accounts for a huge chunk of the messiness.
Airing The Decision on ESPN special was not a great look. To be fair, it did raise millions of dollars for the Boys & Girls Clubs of America, and it was absolutely fantastic theater. But keeping the Cavs in the dark for so long only to spurn them for a premeditated Superteam was considered a betrayal by many—not just to the city of Cleveland, but the integrity of the game.
Burned jerseys and hostile receptions followed The Decision. So did a scathing letter from Cavs governor Dan Gilbert, which was invariably undermined both by its contents and Comic Sans font choice.
Yet it wasn't just LeBron's actual departure that made this a feel-bad separation. It was the extended lead-up to his exit. His free agency was a talking point for years. It didn't just influence how Cleveland went about building a team, either. So many other franchises expended long-term brain power and resources structuring their cap sheets in anticipation of this chase.
On the bright side, this divorce had a happy ending for both Cleveland and Miami for the most part. The Heat won two titles with LeBron, and he then returned home in 2014 and led the Cavs to their first-ever championship two years later.
Carmelo Anthony and the Denver Nuggets (2011)
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Compared to so many of the trade-demand landmines to follow, the divorce between Carmelo Anthony and the Denver Nuggets was fairly tame. The messiness stems from the delay.
Melo was reportedly pushing for the Nuggets to send him to the New York Knicks prior to the 2010-11 season. He eventually opened up his list to incorporate other teams, including the then-Brooklyn Nets and Chicago Bulls.
Denver eventually sent him to the Knicks, but not until February 2011, more than six months after his reported trade request and more than 18 months after Chris Paul reportedly toasted to the formation of a Big Three in the Big Apple with himself, Melo and Amar'e Stoudemire.
Now retired, Anthony has insisted he didn't force a trade to the Knicks. Everyone and their next-door neighbor's third cousin's barber are understandably skeptical.
Regardless of who initiated the divorce, Denver played the situation perfectly under then-lead executive Masai Ujiri. With the Knicks (mostly) bidding against themselves, the Nuggets acquired a smorgasbord of rotation players who helped spearhead a 57-win campaign by 2012-13, as well as the pick that became Jamal Murray, who has since grown into the second-best player on a championship-winning team.
Chris Paul and the New Orleans Hornets (2011)
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Chris Paul's December 2011 trade request did not have to turn messy. He preempted it with a July 2010 toast at Carmelo Anthony's wedding, calling for the formation of a Big Three on the New York Knicks with himself, Melo and the recently Big Apple-bound Amar'e Stoudemire.
Sure enough, the Knicks topped his wish list when the trade request came in. However, the then-New Orleans Hornets did not acquiesce. General manager Dell Demps instead cobbled together a three-team deal with the Houston Rockets and Los Angeles Lakers that would have paired CP3 with Kobe Bryant in Hollywood.
Alas, the league office was in charge of overseeing the Hornets at the time. Then-commissioner David Stern decided to veto the trade, citing now-infamous "basketball reasons." New Orleans instead pivoted to a deal with the Los Angeles Clippers.
Lob City being born at the expense of their then-in-arena rival is actually hysterical—unless you're a Lakers fan, of course.
Ray Allen and the Boston Celtics (2012)
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Ray Allen bolted the Boston Celtics reportedly without much notice during 2012 free agency. That never would have gone over well. But it looked exponentially worse when he fled Beantown for the Big Three-era Miami Heat, to whom the Celtics had just lost in the 2012 Eastern Conference Finals, as well as the 2011 Eastern Conference semifinals.
Did this make Allen a front-runner? Disloyal? Was it just business?
Though it's anticlimactic to say, "just business" feels like the right answer. Allen later explained that he intended to stay with the Celtics, but they wanted to give him less money and bring him off the bench.
That didn't soften the blow among Allen and his former teammates. It took him years to reconcile with Paul Pierce, and then even longer to link back up with Kevin Garnett.
Romantics needn't worry, though. They can now all be in the same arena together again.
Dwight Howard and the Orlando Magic (2012)
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Back in March 2012, Dwight Howard seemingly positioned himself to orchestrate a trade from the Orlando Magic to the then-New Jersey Nets. Then he suddenly bailed on that plan, choosing instead to remain in Orlando because...he had fun on a team plane ride one night.
Of course, this was far from the end of it. Howard finished the lockout-shortened season in Florida, but not without drama. Most notably, he caused one of the most bizarre moments in NBA history when he party-crashed the press conference of then-Magic head coach Stan Van Gundy, who was explaining to reporters that he knew Howard wanted him fired. Awkward much?
Howard finished the season injured, laboring through back issues that prevented him from playing in Orlando's first-round exit against the Indiana Pacers. By the time that summer rolled around, he was ready to leave again.
The Magic traded him to the Los Angeles Lakers in a four-team deal that August which they actually ended up winning in hindsight. And so began Howard's tenure as the league's foremost flip-flopper.
Dwight Howard and the Los Angeles Lakers (2013)
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This is basically the Dwight Howard and Kobe Bryant breakup when you really think about it.
The Los Angeles Lakers assembled a formidable core for the 2012-13 season when they paired Kobe and Pau Gasol with Howard and Steve Nash the previous summer. What followed was anything but formidable.
Nash battled injuries. Head coach Mike Brown was fired five games into the season after the Lakers got off to a 1-4 start. Mike D'Antoni eventually took over, inheriting what appeared to be a discordant relationship between Kobe and Dwight, even if they all mocked it.
Los Angeles' season ended in mega disappointment. Kobe suffered a torn Achilles that altered the rest of his career, and Howard entered free agency facing questions about his toughness and dedication to the team.
The Lakers (re-)courtship of him was...weird. It featured a cringe "#StayD12" movement that reeked of desperation and included Kobe offering Howard to teach him how to be a champion. The end result: Howard left for Houston, from where his rocky relationship with Kobe got worse.
Years later, Dwight would say he gained a new perspective on the entire saga.
Kevin Durant and the Oklahoma City Thunder (2016)
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There is no scenario in which Kevin Durant's free-agent departure from the Oklahoma City Thunder in 2016 would have been accepted without impassioned push-back. He exacerbated the inevitable response by doing what many both inside and outside of OKC considered the worst possible decision: joining the Golden State Warriors.
These were the same Warriors that were fresh off winning an NBA-record 73 regular-season games. The same Warriors who already had Stephen Curry, Draymond Green and Klay Thompson. The same Warriors who had just erased a 3-1 Western Conference Finals deficit to beat KD's Thunder and return to the NBA Finals, where they would blow a 3-1 lead of their own to LeBron James and the Cavs.
Durant's decision has since been dissected ad nauseam. It's not hard to see why. There is no overstating the impact this decision had on the entire NBA.
The Dubs went on to win the next two championships. The Thunder were thrust into a completely different timeline. Durant suffered a torn Achilles during his final game in a Golden State jersey. The league implemented cap-smoothing in the most recent collective bargaining agreement to avoid another KD-to-the-Dubs scenario.
Oh, the nickname "Cupcake' is involved as well.
Most of all, this divorce left Durant living in the gray. He is clearly one of the greatest players in NBA history, but he's also since compiled a borderline-journeyman's resume that makes it difficult for any one fanbase to claim him as its own.
Kyrie Irving and the Cleveland Cavaliers (2017)
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Who requests a trade after making three consecutive NBA Finals, winning one title and hitting one of the biggest shots in league history? Kyrie Irving does.
This breakup seemingly came out of nowhere. It was a shock when the news broke in August 2017, not far off from training camp, that he would be landing with the Boston Celtics.
"Why would Kyrie do this?" was a default refrain. Was he aggravated with LeBron James? Did he simply want a chance to run his own team? Or did he see the writing on the wall, with many expecting LeBron to bolt the following summer, which he ultimately did?
Perhaps it was a combination of all three. At any rate, this trade altered the course of more than a few franchises.
Despite assertions that the Cleveland Cavaliers got the better end of the deal, even after red flags cropped up on Isaiah Thomas' physical, they barely made it back to the NBA Finals, where they were promptly swept by the Golden State Warriors. LeBron ended up leaving in 2018 to join the Lakers, setting the stage for an Anthony Davis trade in 2019.
Meanwhile, Kyrie was injured by the time his Celtics met the Cavs in the 2018 Eastern Conference Finals, after having what many considered the best regular season of his career. His time in Boston wouldn't last much longer.
Kawhi Leonard and the San Antonio Spurs (2018)
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"Messy" and "divorce" are not terms often associated with the San Antonio Spurs. They are among the NBA's gold standards for drama-free sustainability.
However, their breakup with Kawhi Leonard in 2018 was anything but drama-free. It was layered and weird.
San Antonio's handling of its Finals MVP's right quad injury is often cited as the driving force. There was a clear disconnect between the player and organization on his prognosis, and it spilled into the locker room, culminating in Tony Parker and Manu Ginobili confronting Kawhi about his status.
In the time since, we've also learned that Leonard perhaps wanted more preferential treatment than San Antonio offered. He also wanted to be back in California, where he was born, went to high school and attended college. And it still isn't clear how much influence was held by the now-notorious "Uncle Dennis," who became a more prominent part of Kawhi's camp following the departure of his previous representatives, Brian and Frankel Elfus.
The nail in the coffin was the Spurs' approach to Kawhi's supermax eligibility. He could have signed a five-year, $219 million deal as of July 2018. Many wondered whether the Spurs would even offer it after Leonard appeared in only nine games during the 2017-18 campaign. Others contemplated whether Kawhi would even sign it, because he may have been that determined to wind up in L.A.
A trade to the Toronto Raptors was the end result. Despite the gradual descent in the Kawhi-Spurs dynamic, the whole thing felt sudden and unsavory. It turns out there was really a relationship Gregg Popovich couldn't salvage. And San Antonio's return—DeMar DeRozan, Jakob Poeltl and the pick that became Keldon Johnson—was widely panned in the moment as well as long after. Especially when they also shipped Danny Green north of the border.
After landing in Toronto, Kawhi immediately proceeded to win another title and Finals MVP. He then left the Raptors to link up with Paul George on the Los Angeles Clippers in 2019, where he's been ever since.
Leonard has battled scattershot availability ever since, becoming one of the league's greatest what-ifs ever, in addition to being the quiet, no-nonsense star who left the quiet, no-nonsense Spurs in a loud, nonsensical-filled soap opera.
Jimmy Butler and the Minnesota Timberwolves (2018)
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Jimmy Butler's 2017 arrival in Minnesota was viewed as a hallmark moment for the Timberwolves. This was the franchise who lost stars, not acquired them. Team president and head coach Tom Thibodeau was flipping the script.
For a while, it appeared to work. The Wolves had the look and feel of a contender in 2017-18 before Butler suffered a meniscus injury that effectively derailed their season. No matter, though. There would be more time to make deep playoff runs.
Or not.
Annoyed by Minnesota's unwillingness to renegotiate-and-extend his contract, Butler embarked on one of the most public trade demands of all time. It included a "tour de force" during practice in which he reportedly taunted Wolves executives and teammates. He then gave a candid interview with Rachel Nichols, then of ESPN, and reiterated his trade request. How convenient, right?
Thibodeau loved it all, because of course he did. He truly believed the Wolves could let this situation spill into the regular season. Not surprisingly, he was wrong. Minnesota shipped Butler to the Philadelphia 76ers before Thanksgiving.
Nobody came out of this ordeal better for the wear, which makes for an interesting present-day playoff series—particularly after Jeff Teague, who was on those Wolves, recently called Butler the most hated person in Minnesota.
Anthony Davis and the New Orleans Pelicans (2019)
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Anthony Davis requested a trade from the New Orleans Pelicans right before the February 2019 trade deadline (while sidelined with a finger injury), which has since become a textbook play for superstars. He was a year-and-a-half out from free agency, a weird not-so-sweet spot in which the Pelicans couldn't necessarily drum up top-shelf offers from suitors that weren't near the top of his wish list.
Davis' trade request technically didn't backfire. But it was not granted swiftly.
New Orleans held onto him past the trade deadline, creating a beyond-awkward dynamic in which he kind of, sort of played out the season, except not really. Davis missed the Pelicans' final seven games, as they sought to jazz up their draft-lottery odds, and he showed up to their final game wearing a "That's all folks!" shirt that he definitely had no hand in selecting or, apparently, putting on.
As expected, New Orleans sent him that summer to the Los Angeles Lakers, with whom he won a title the following season. The Pelicans got plenty in return—Lonzo Ball, Josh Hart, Brandon Ingram and draft picks. They were also fresh off winning the Zion Williamson sweepstakes at the lottery, which made the teardown slightly more palatable.
However, it did perpetuate the franchise's cycle of building around injury-prone stars whom everyone believes actually want to be somewhere else.
James Harden and the Houston Rockets (2021)
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James Harden's exit from the Houston Rockets should be remembered as a slow, years-long burn.
His relationship deteriorated with Chris Paul after just two seasons, which prompted the franchise to acquire Russell Westbrook at his behest. The Rockets gave up a ton to make it happen and were rewarded with a second-round exit that nearly saw them bow out in the first round against the CP3-led Oklahoma City Thunder.
When the Harden-Westbrook dynamic fell predictably short, the writing was on the wall. And the message was written in Sharpie. Houston sent Russ to the Washington Wizards in a deal for John Wall, and Harden's attempt to extricate himself began in earnest.
The 2018 MVP skipped the start of 2020 training camp to hang out with Lil Baby in Las Vegas. Just before the start of the season, he was fined $50,000 by the league for violating its health and safety protocols while attending a party. Though he began the year by hanging 44 points on the Portland Trail Blazers (in an overtime loss), Harden's effort level came under siege fewer than five games into the season.
Eventually, after telling reporters that the Rockets were "just not good enough" after a blowout loss to the Lakers, The Bearded Wonder got his wish. The Rockets sent him to the Brooklyn Nets to form a Big Three with Kevin Durant and Kyrie Irving, completing what has since turned out to be the first of three messy exits.
James Harden and the Brooklyn Nets (2022)
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After forcing his way to Brooklyn, James Harden's time with the Nets was incredibly short-lived. And that's putting it charitably.
Injuries impacted his availability upon arriving, and he was banged up midway through the team's 2021 playoff push. He returned in time to finish the series against the Milwaukee Bucks, but Kyrie Irving was also injured, Kevin Durant has big feet, and the Nets lost.
Every member of Brooklyn's Big Three was penciled in for an inevitable extension. However, Harden began to change his tune during the 2021-22 campaign. The reasoning is still hazy, but Kyrie's refusal to get the COVID-19 vaccine led to more scattershot availability and a noticeably less-inspiring Nets window. So, you know, it's not hard to read between the lines.
This exit wasn't nearly as messy as Harden's extrication from Houston—and from Philadelphia, for that matter. In this case, he seemed more worried about the optics, resisting the urge to make a "formal" trade request out of fear for the backlash he'd receive. He inevitably got his way, reuniting with Daryl Morey in Philly, running back a partnership that would surely never end as badly. (Spoiler alert: It did.)
In retrospect, this divorce marked the official end of a Nets era. Brooklyn forked over Jarrett Allen, Caris LeVert, four first-rounders and three swaps for 89 combined regular-season and playoff appearances from Harden, only 365 minutes of which saw him line up alongside Kyrie and KD.
Even with the Nets in a better place now (because they have an actual direction), the messiness of this divorce lies in the dearth of payoff they received from their all-in investment.
Ben Simmons and the Philadelphia 76ers (2022)
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The Philadelphia 76ers traded Ben Simmons to the Brooklyn Nets in 2022, but their breakup started months earlier during the 2021 playoffs.
Coming out of a second-round loss to the Atlanta Hawks in which Simmons shot 15-of-45 at the free-throw line (33.3 percent) and then passed up a wide-open dunk during crunch time in Game 7, his status in Philly essentially imploded. Then-Sixers head coach Doc Rivers eschewed the opportunity to defend him in the aftermath. Joel Embiid minced words but not intentions, calling Simmons' Game 7 decision the "turning point."
Simmons' representatives began discussing his future with the Sixers, or lack thereof, almost immediately afterward. There were rumblings he wouldn't report to training camp. He rebuked teammates' attempts to visit him. Embiid called Simmons' approach disrespectful. The Sixers started withholding his salary.
Simmons eventually reported to the team, but he was suspended for the season-opener after being thrown out of practice by Rivers for refusing to sub in for drills.
As it turned out, Simmons would never take the floor in a Sixers uniform again. He stayed away from the team due to issues both with his back and mental health, the latter of which became grotesque fodder for discussion.
Philly refused to simply move him until it could find the best deal possible, dragging out the saga. That deal materialized in advance of the 2022 trade deadline when Sixers team president Daryl Morey finagled a reunion with James Harden, bringing one of the NBA's longest, most awkward trade-demand ordeals to a merciful end (arbitration over unpaid salary notwithstanding).
Kyrie Irving and the Brooklyn Nets (2023)
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At one point, it looked like the Big Three-era Brooklyn Nets would run roughshod over most of the NBA for a fairly extended window. So much for that.
Injuries played a role in derailing Kyrie Irving's time in Brooklyn. He played only 20 games during the 2019-20 season and missed the end of the Nets' second-round series against the Milwaukee Bucks in 2021. In 2021-22, he appeared in only 29 games amid his refusal to get the COVID-19 vaccination, which played at least a partial role in James Harden fleeing for the Philadelphia 76ers.
Jump ahead to 2022-23, and his future in Brooklyn was already in doubt. He wanted a contract extension that the Nets weren't prepared to give. Brooklyn also suspended him for propagating anti-semitic beliefs and rhetoric on social media and then refusing to apologize at first.
By the time February 2023 rolled around, Kyrie officially requested a trade. The Dallas Mavericks took a chance on him, which was working out quite well prior to his recent ACL injury.
The Nets, on the other hand, accepted a package built around Spencer Dinwiddie, Dorian Finney-Smith and draft equity. That set the stage for the Kevin Durant selloff and eventual entry into the rebuild they're working through now.
James Harden and the Philadelphia 76ers (2023)
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It is August 2023. James Harden is hosting an Adidas marketing event in China. He is asked to comment on his status with the Philadelphia 76ers, the team to which he forced a trade not even two full seasons ago.
"[Sixers team president] Daryl Morey is a liar, and I will never be a part of an organization that he’s a part of," Harden said. "Let me say that again: Daryl Morey is a liar and I will never be a part of an organization that he’s a part of.”
These comments came after the Sixers reportedly ghosted Harden in the days leading up to free agency. They were also a clear attempt by Harden to force Philly's hand following his trade request.
Morey and the Sixers held out—for a time. And generally speaking, while no one came out of this looking squeaky clean, support tilted toward the executive and organization. People never quite got over Harden's lackluster postseason(s), after which he lamented that the ball didn't find him, even though he was the team's point guard and primary ball-handler.
True to his trade-demand form, Harden did not immediately show up when the Sixers reported for training camp in October 2023. He wasn't ready to play when the season opened up, and just four games into the year, Morey acquiesced and sent him to the Los Angeles Clippers, Harden's preferred destination.
Philly made out quite well with its compensation given the lack of suitors beyond the Clippers. The return also let Morey position the Sixers for plenty of 2024 cap space, which they used to...poach Paul George from the Clippers themselves.
That trickle-down effect was celebrated in real time, but it has since become another source of uncertainty and frustration for Philly sports fans, particularly for those who like player-hosted podcasts.
Luka Doncic and the Dallas Mavericks (2025)
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Relative to pretty much every other NBA breakup ever, Luka Dončić's departure from the Dallas Mavericks is unique in its messiness. So much of the chaos and ugliness has unfolded after his exit.
Luka's relationship with Mavs general manager Nico Harrison reportedly eroded over time, if it was ever in a good spot in the first place. But even as whispers of dissent and frustration reached outer NBA circles, they never came across as "Defcon He's About To Get Traded To The Los Angeles Lakers."
Well, that is exactly what happened. The move was initially—and continues to be—viewed as perhaps the most shocking and inexplicable decision of all time. For all of his flaws, Peak Luka is a transcendent superstar. Tim Duncan and Kevin Durant are the only other players to nab as many first-team All-NBA selections (five) as Dončić before their 26th birthday.
The irrationality of it all has led to a nasty fallout. Harrison and Mavericks team governor Patrick Dumont have each given largely incoherent justifications behind the deal. Luka's weight, work ethic and lifestyle have been dragged through the mud. Mavs fans are understandably both heartbroken and irate. And Dallas seemingly remains a blob of disorder behind the scenes.
Ripple effects from this trade will be felt for years to come, if not decades. Luka's hobbled close to the season in L.A. may leave room to wonder whether Harrison was on to something and just poorly executed it. That possibility feels remote.
This decision is more likely to go down as unparalleled chaotic incompetence than anything else.
Jimmy Butler and the Miami Heat (2025)
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Jimmy Butler went from embodying Miami Heat culture to defying it seemingly overnight.
Team president Pat Riley called out Butler for trolling the Boston Celtics during the 2023 playoffs after the six-time All-Star missed Miami's own brief postseason push with a right MCL injury. "If you're not on the court playing against Boston or on the court playing against the New York Knicks, you should keep your mouth shut on the criticism of those teams," Riley said.
Beyond that, the Heat's lead executive equivocated on whether the team would extend Butler that summer, citing his age and health. In hindsight, that moment was clearly the beginning of the end.
Butler sent a warning shot by showing up to 2024 media day with "normal hair" and "no shenanigans." Before the calendar flipped to 2025, he had indicated he would rather be elsewhere. And after the New Year, he reiterated as much during a face-to-face meeting with Riley, through the media and more passive-aggressively with his play.
Miami wound up suspending him multiple times after his initial trade request. Finally, he delivered a tour-de-fart effort in a Jan. 21 loss to the Portland Trail Blazers. It was the final time he would suit up for the Heat, who flipped him to the Golden State Warriors shortly before the 2025 trade deadline.
In navigating this nightmarish stretch, Miami learned the same lesson taught to Minnesota before it: There is no such thing as an un-messy Jimmy Butler breakup.
