Top 15 Most Awkward Breakups in NBA History

One of the major facets of success in the NBA is teamwork. A franchise has to work together on all fronts to win a championship. The owner, general manager, the coaches and, of course, the players all

One of the major facets of success in the NBA is teamwork. A franchise has to work together on all fronts to win a championship. The owner, general manager, the coaches and, of course, the players all need to be on the same page to get to the biggest prize in the sport. One flaw in the system can insert negativity into the mix, which harms a team's chances of success. Of all the relationships on a successful team, the players have to get along with each other. If you can’t trust the person you’re sharing the ball with, things will get ugly very fast.

There have been plenty stories of players failing to get along and ruining a good thing. Many good teams will see egos get into the picture and cause issues to flare up between star players. This is every general manager and coach’s nightmare. There are also the times when a franchise, fan base or coach gets sick of a player’s attitude. It is extremely easy in professional sports for a star to go from fan favorite to public enemy number one at the drop of a dime. The money, power and fame associated with sports causes these situations to come up often.

This list will look at interesting relationships that ended on an awkward note. There are many players that have been traded, left in free agency, were brought out or just got told the team no longer wanted them. The NBA is the most star driven league in sports and that will allow players to have more influence. This has led to the stories we’re looking at and we’ll examine the fifteen NBA relationships that ended on awkward notes.

Continue scrolling to keep reading

Click the button below to start this article in quick view

Start Now

15 LeBron James and the Miami Heat 

Steve Mitchell-USA TODAY Sports

The relationship between LeBron James and the Miami Heat was a definite success. Miami made the Finals in all four seasons with James as their superstar and won two NBA Championships. James became an even bigger superstar there and was a polarizing figure in the sports world. Entering free agency again, James decided to leave the Heat to return home to the Cleveland Cavaliers. The problem is he didn’t inform the Heat until the day of the decision. They allegedly drafted Shabazz Napier to appease him and made a few veteran signings to plan for another season with James, but he left them high and dry.

14 Dwight Howard and the Orlando Magic 

Dwight Howard is one of the greatest players in Orlando Magic history. He gave them some solid years of success as the best center in the NBA. As Howard was entering free agency, there were rumors of him wanting to go to the Brooklyn Nets or Los Angeles Lakers in the summer. Orlando convinced him to sign an extension, but he immediately regretted it. There was a situation where Stan Van Gundy told the media that Howard wanted him fired, before Howard walked up and awkwardly hugged his coach. Howard wanted out and was eventually traded to the Lakers, where he was also unhappy.

13 DeAndre Jordan and the Dallas Mavericks 

Kevin Jairaj-USA TODAY Sports

A relationship that never technically started had one of the most awkward endings in recent sports memory. DeAndre Jordan agreed to sign with the Dallas Mavericks on a long-term contract this past summer and Mark Cuban was celebrating finally getting a big free agent name. The problem was that Jordan went back on his word before signing the actual contract and decided to go back to the Los Angeles Clippers. The opening free agent week passed and the Mavericks missed out on all other credible options. Cuban was rumored to be driving around Texas looking for Jordan’s home to try to get him back, but it was for nothing. Naturally, there’s still bad blood between the two sides.

12 J.R. Smith and the New York Knicks 

Anthony Gruppuso-USA TODAY Sports

J.R. Smith was an instant hit with the New York Knicks, as his exciting style of play and hot streaks captured the fan base. New York achieved a little success with Smith as a sixth man off the bench but things started to fall apart quickly. Smith’s play declined and the Knicks went into a terrible slump. Phil Jackson decided to trade Smith and Iman Shumpert to the Cleveland Cavaliers for very little in return. Smith went on to help the Cavaliers reach the NBA Finals but he has no love for the Knicks organization. Jackson claimed Smith’s love life troubles played a part in his poor play and Smith was frustrated that Jackson would even discuss that.

11 Dion Waiters and the Cleveland Cavaliers  

David Richard-USA TODAY Sports

Dion Waiters was drafted by the Cleveland Cavaliers to become one of their core stars of the future. When LeBron James decided to come home and sign with Cleveland, Waiters boasted that he and Kyrie Irving would become the best starting backcourt in the NBA. Unfortunately for Waiters, he could not live up to that billing the way Irving did. The Cavaliers traded Waiters after a couple of months and Waiters wasn’t happy about the way it went down. Waiters claims he didn’t hear from LeBron James following the trade and implied James’ power in the organization influenced the move. There was also various rumors about Waiters having issues with Kyrie Irving.

10 Deron Williams and the Brooklyn Nets 

Brett Davis-USA TODAY Sports

The Brooklyn Nets are in a horrible place right now in the NBA and the main reason for that is Deron Williams. On the precipice of moving from New Jersey to Brooklyn, the Nets traded for Williams in hopes of becoming a contender and a relevant franchise with a new superstar. Brooklyn would trade many more assets and draft picks to acquire big name talent to place around Williams. Sadly for the Nets, Williams failed to ever live up to his massive contract and ended up harming the team. Williams requested a buyout last summer and Brooklyn agreed to pay him $25 million to disappear. Both parties showed negativity towards each other and fans will be ready to boo him in his first game back in Brooklyn.

9 Larry Sanders and the Milwaukee Bucks 

Tom Szczerbowski-USA TODAY Sports

Due to his physical gifts and defensive skills, Larry Sanders was one of the most promising young big men in the NBA. The Milwaukee Bucks seemed to strike gold with the league's best shot blocker and signed him to a four year, $44 million contract. Things went downhill between the two parties after that peak with Sanders getting injured in a nightclub fight and later getting suspended for violating the NBA's drug policy. Sanders decided to leave the NBA to get his life on track and enjoy the small things in life. The Bucks reached a buyout and will be paying him $1.9 million over the next few years. Imagine having to pay your ex in multiple payments over seven years...

8 Patrick Ewing and the New York Knicks 


Many would argue that Patrick Ewing is the greatest New York Knicks star in franchise history. Ewing delivered greatness for many years but was met with criticism for failing to lead the team to a championship. Still, Ewing had the career of someone that should have spent his entire time in the NBA with one team. After injuries and age started to get the better of him towards the end of his career, New York made the unpopular decision to trade their legend to the Seattle SuperSonics for Glen Rice and role players. Ewing played another two seasons but it felt bizarre seeing him outside of the blue and orange uniform. A popular team getting rid of their franchise player is always extremely awkward to watch play out.

7 Phil Jackson and the Los Angeles Lakers (first time) 

The story between head coach Phil Jackson and the Los Angeles Lakers has been bizarrely full of ups and downs. Following a dynasty with three championships and plenty of success, the Lakers decided to part ways with Phil Jackson. Most stories indicate that Kobe Bryant was gaining power in the organization and used it to get Jackson removed from the position. Jackson wrote a book criticizing Bryant and it seemed like their relationship was done for good. Wrong. Los Angeles rehired him just one year later and he coached them to another pair of NBA Championships. The story ended well, but his first departure and return is one of those weird stories you can’t make up.

6 Ray Allen and the Boston Celtics 


Ray Allen was one of the best pure shooters in NBA history but he didn’t win his first Championship until being traded to the Boston Celtics. Along with Kevin Garnett and Paul Pierce, Allen was a member of the original “big three” and they won a title in their first season together. The unit would compete and have other memorable runs but Allen eventually decided to leave Boston. That was bad enough, but he chose to sign with their enemy, LeBron James and the Miami Heat. Garnett and Rajon Rondo didn’t speak fondly of his decision to leave and Garnett didn’t even want to shake his hand or give him a high-five when the teams met for the first time.

5 Gilbert Arenas and the Washington Wizards 


Gilbert Arenas became a star out of nowhere for the Washington Wizards. As he emerged as one of the best scorers in the NBA, Arenas led the Wizards back to relevancy with his exciting style of play and unique personality. This was all until one infamous incident that saw Arenas and teammate Javaris Crittenton bring guns into the locker room and have an argument about gambling debts. Arenas was suspended and served time in a halfway house before returning to the Wizards. While he played for them again, they traded him as quickly as possible to the Orlando Magic. There’s no doubt the gun incident played a role in the once wonderful relationship ending.

4 Dwight Howard and the Los Angeles Lakers 

Richard Mackson-USA TODAY Sports

As mentioned earlier on the list, Dwight Howard had an awkward departure from the Orlando Magic and was traded to the Los Angeles Lakers. It seemed like a perfect fit for the Lakers, as they looked to make a title run with Howard, Steve Nash and Kobe Bryant leading the way. Howard was unable to get along with his teammates and developed a terrible reputation in the NBA. Bryant viewed him as soft, Nash was seen yelling at him in a game and fans didn’t appreciate him. Just one season into the experiment, Howard decided to explore his free agent options and left for the Houston Rockets. Bryant and Lakers fans took shots at Howard in one of the more embarrassing ways a star has left an NBA team.

3 LeBron James and the Cleveland Cavaliers 


All that ends well is forgiven? Perhaps, but it isn’t forgotten. LeBron James created quite a spectacle when he brought “The Decision” to ESPN television and announced on national television that he would be leaving the Cleveland Cavaliers for the Miami Heat. The choice to form a super team with two close friends was one thing, but leaving the city that worshiped him in such fashion caused a negative reaction. Cleveland fans burned his jerseys and anointed him as their biggest enemy. Eventually, James decided he wanted to come back home and he’s now loved again, so I guess this awkward breakup has a happy ending.

2 Michael Jordan and the Chicago Bulls (first time) 


Many of the stories of NBA relationships ending awkwardly have been due to bad blood between the two parties but Michael Jordan leaving the Chicago Bulls in 1993 was a different case. Jordan decided to leave the Bulls and retire from the NBA to pursue a career in the MLB. There are many theories out there about why Jordan decided to do this but no one really is certain of his reasons. The only things that are certain is that an iconic athlete left a dynasty at the peak of his career to try a different sport and that it was one of the strangest things to happen in sports history. Jordan returned to the Bulls in 1995 and delivered another three-peat before retiring once again.

1 Shaquille O’Neal and the Los Angeles Lakers 


No NBA relationship ended as awkwardly as the one between Shaquille O’Neal and the Los Angeles Lakers, or rather O’Neal and Kobe Bryant. The two superstars formed one of the best duos in NBA history. O’Neal was the established iconic center and Bryant was the rising star guard creating his legacy. The two delivered three consecutive championships together but they simply couldn’t get along. Shaq’s humorous personality and Bryant’s strict demeanor caused the two to have clashes and their differences turned into a personal hatred. The Lakers decided to invest in the younger Bryant and traded O’Neal out of town to the Miami Heat. Shaq won a title on his own first but Bryant would get another two later without him. Both men have respect for each other now, but their hatred caused the most awkward NBA breakup.

Give TheSportster a Thumbs up!

Looking for an AD FREE EXPERIENCE on TheSportster?

Get Your Free Access Now!

More in Wrestling

Top 15 Most Awkward Breakups in NBA History