The 8 Ugliest Breakups in the NBA Since 2000

Breakups are hard.

That phrase typically applies to romantic relationships, but it certainly extends to the NBA. Players feud with other players, players grow bitter in the organization, ownership stops trusting coaches and basically every other combination imaginable.

In many cases, the malcontent is quietly managed or quickly forgotten. But sometimes, it becomes a very public unraveling.

Since 2000, the NBA has included its fair share of strange, spiteful and awkward separations. Ordered chronologically, let's recap some of the most cringeworthy breakups in the league.

Note: The single-most disastrous breakup is between Gilbert Arenas and Javaris Crittenton, but that 2009 confrontation is both heavily layered and included legal repercussions. It is not included.

After retiring in 1999, Michael Jordan became the president of basketball operations for the Washington Wizards in 2000. He ended up returning to the floor in 2001 with the full expectation of resuming his front-office job upon his next retirement.

But that didn't happen.

Washington owner Abe Pollin changed his mind because of three factors. At the time, an Associated Press report cited "player dissension, a franchise faltering after the years of Jordan in charge, and deteriorating relationships throughout the organization."

Years later, Abe's wife, Irene Pollin, published a memoir that detailed how MJ responded to the unexpected news.

"Michael stormed out of the room, went down to the parking garage, jumped into his Mercedes convertible with Illinois license plates, took the top down and drove directly back to Chicago."

As the final buzzer sounded in the 2004 NBA Finals, it also signaled the end of the Los Angeles Lakers' dynasty. That loss to the Detroit Pistons in Game 5 is the final moment Shaquille O'Neal and Kobe Bryant shared the floor as Lakers teammates.

Given what happened before the season, it was no surprise. Bryant criticized Shaq for being "fat and out of shape" and poor leadership as the result of trying to negotiate a contract extension.

However, this wasn't simply a Shaq-Kobe disagreement.

Not only did Los Angeles not renew Phil Jackson's contract, but the Lakers also refused to give O'Neal the contract he desired. As a result, he demanded a trade and landed with the Miami Heat.

The tension between O'Neal and Bryant ultimately subsided. Shaq spoke at his teammate's memorial service in 2020, too.

Vince Carter headlined a memorable era for the Toronto Raptors, and he remains the franchise's leader in points per game. But he didn't exactly leave on good terms.

His trust in the front office deteriorated over a long process that included the "controversy" of Carter participating in graduating ceremonies at North Carolina on the morning of a Game 7 and missing a potential winning shot that night in 2001. Carter didn't believe in team president Richard Peddie, who reportedly lied to his superstar about the search for a general manager in 2004.

The result was a blockbuster trade to the New Jersey Nets. For basically a decade, fans booed Carter whenever he returned to the Air Canada Centre.

Fortunately, this story also has a happier ending.

When the Raptors celebrated their 20th anniversary in 2014, they showed a video highlighting Carter's career. After the boos turned to a standing ovation, Carter—then a member of the Memphis Grizzlies—waved to the crowd while wiping away tears.

LeBron James arrived as The Chosen One. In seven seasons with the Cleveland Cavaliers, he lived up to the billing in every way—a Rookie of the Year, scoring champion, All-Star and league MVP—except the one that mattered most: winning an NBA title.

So in 2010, he left. James formed a Big Three in Miami alongside Dwyane Wade and fellow free agent Chris Bosh.

And, uh, the aftermath wasn't awesome.

While jersey-burning videos flooded the internet, Cavs owner Dan Gilbert published his iconic Comic Sans letter. It never mentioned LeBron by name but pointed to his "shocking act of disloyalty" and promised Cleveland fans that the organization would win a championship before LeBron did.

Long story short? LeBron won two titles in Miami. Then he returned to the Cavaliers in 2014 and guided them to a championship over the Golden State Warriors in 2016.

LeBron's departure from Cleveland for the Lakers in 2018 had nowhere near the level of animosity.

Prior to the lockout-shortened 2011-12 season, Dwight Howard publicly revealed a trade demand away from the Orlando Magic. He backed off the request at the trade deadline, waiving his opt-out clause to stay with Orlando for at least one more season.

Behind the scenes, though, unrest remained—until it was painfully, uncomfortably in the open.

During an April interview, Magic coach Stan Van Gundy said he heard "right from the top" that Howard wanted him fired. Moments later, Howard interrupted the interview and put his arm around Van Gundy, who quickly exited the scrum of reporters.

Howard denied the rumor, but neither their relationship nor individual tenures in Orlando could recover.

Orlando dismissed Van Gundy following the first-round exit and dealt Howard to the Lakers in the summer.

When the Boston Celtics won an NBA title in 2008, Ray Allen shared the spotlight with Paul Pierce, Kevin Garnett and Rajon Rondo. But when Rondo organized a 10-year anniversary celebration of that championship, Allen didn't receive an invite.

Oh, this is a big-time grudge.

In the 2012 playoffs, the Celtics lost to Miami in a seven-game series. During the summer, Allen signed with the Heat—and, according to Kendrick Perkins—didn't communicate with his teammates, either. Allen's departure pained Garnett so much he said, "I don't have Ray's number anymore" at media day before the next season.

One year later, Allen said he still hadn't spoken to Pierce and Garnett. And five years after that, the Rondo-led vacation didn't include Allen on the reunion trip.

Pierce and Allen have since reconciled, but the bitterness between him and others may still be lingering.

Four summers after Allen's exit for Miami, Kevin Durant made a similar decision. He played nine seasons for the Seattle SuperSonics and Oklahoma City Thunder, spending all eight in OKC alongside Russell Westbrook, but he left the Thunder for the Warriors.

Just as Miami had defeated Boston before Allen's signing, Golden State had eliminated OKC in the Western Conference Finals.

The timing only added to the controversy of Durant's choice. It probably didn't help Durant told Westbrook about the decision in a text, which is basically What Not To Do in A Breakup 101.

Westbrook, understandably, expressed his frustration.

The All-Star guard took an indirect shot through Instagram, posting a picture of cupcakes reportedly to call Durant soft. Durant seemingly embraced the joke, later posing with cupcakes and even designing a shoe called the KDX Red Velvet in 2017.

Durant has repeatedly silenced any questions about a feud, and there's no evidence of that anyway. But in the moment, his departure from OKC created a firestorm.

In hindsight, LeBron joining the Heat is a critical part of Cleveland's championship story. Without him, the Cavaliers plummeted from a 61-21 record to 19-63 and ended up securing the No. 1 pick in the 2011 NBA draft.

That selection? Kyrie Irving, who buried the winning shot in Game 7 of the 2016 NBA Finals against Golden State.

But after losing to the Warriors in the 2017 Finals, Irving requested a trade. Despite the Cavaliers' chances of winning more titles, he grew tired of playing in LeBron's shadow and wanted a featured role. LeBron reportedly felt "devastated" at Irving's choice.

While this breakup wasn't bitter like Allen's, the shock of Irving's request to leave a top contender made it memorably ugly.