Breakups are never fun, and it’s no different in the NBA. Entire organizations or even cities are often heartbroken thanks to the actions of one player. There is a long history of messy NBA breakups, but these are the worst ones.

Messiest NBA Breakups

3. Kevin Durant leaves the Oklahoma City Thunder

We all know the story here, as it's the most recent NBA breakup on our list. Kid gets drafted by a small-market team. He quickly becomes a folk hero for a hungry fanbase. Eventually, they become an MVP-caliber player and reach the Finals.

The Cinderella story ends when the team can’t win it all. The player starts looking around and leaves for greener pastures.

This story could fit several players, but Kevin Durant going to the already stacked, 73-win Golden State Warriors was the latest and most striking instance.

In an instant, one of the most beloved players in the league became a villain. It was a truly one-sided NBA breakup. Some called him a snake for his actions. The burning of Durant jerseys ensued.

Imagine Superman being immune to Kryptonite. That’s basically what the Warriors were with Durant. Durant’s decision to walk away from OKC changed the NBA landscape for years.

2. Kobe Bryant and Shaquille O’Neal split

While there have been many messy NBA breakups, there are even more NBA what-ifs. What if Derrick Rose never got hurt? What if the Detroit Pistons didn’t draft Darko Miličić over Dwyane Wade, Carmelo Anthony, and Chris Bosh?

One of the biggest ones, however, is what if Kobe Bryant and Shaquille O'Neal stayed together longer in LA? The duo was absolutely dominant playing together.

O’Neal on his own was already a bad dream for opponents, but paired with an athletic Kobe and his fearless drives, they were a nightmare to play against.

This pairing and the roster around them won three straight championships for the Purple & Gold from 2000 to 2002.

Kobe and Shaq made their now famous NBA breakup after falling short in the 2004 Finals against the underdog Detroit Pistons. The two had an ongoing beef and clashing egos. Eventually, O’Neal was traded to the Miami Heat.

In an episode of the “All The Smoke” podcast, Lakers owner Jeanie Buss set the record straight on this matter. She said that Shaq was moved for money reasons.

1. LeBron James takes his talents elsewhere (the first time)

For most of the 90s, the Cleveland Cavaliers were a mediocre team. Sure, they would get to the playoffs, but everyone knew they weren’t a real threat. Also, it didn’t help that a certain number 23 was around in Chicago at the time.

Then Cleveland's fortunes changed when the NBA Draft lottery went their way. They now had the first overall pick and the right to select the most hyped NBA prospect ever, another number 23 – LeBron James.

The Cavs quickly became must-watch basketball. It was the start of a fairy tale. The team was led by the Chosen 1 (reference to LeBron’s back tattoo), the hometown kid.

Somehow, James exceeded the high expectations placed on him. In just his fourth season, he carried Cleveland and its unimpressive roster to the NBA Finals.

LeBron would do some more heavy lifting in the coming years, but he always coming up empty-handed when it came to rings, leading so perhaps the messiest NBA breakup the league has ever seen.

James had to make a decision in 2010 about his future, ultimately taking his talents to South Beach to win a championship. He successfully did so twice.

The Cleveland franchise and its fanbase were devastated. Just like that, Ohio’s favorite son was no more.