No matter the condition or circumstance, NBA organizations and their players are the heart and soul of the league. With that being said, organizations strive real hard to get ahead of the pack with their decisions and choices. Unfortunately, even the NBA’s most successful model organizations cannot escape the inevitable failure.

Despite the failure, there are teams that easily bounce back from a blunder. Sadly for some, the regretful consequence takes seasons to recover.

Here are five of the most regretful decisions an NBA team has made over the last 20 years.

adam silver

David Kahn running a team

It is still a baffling question on how or even why David Kahn was given an upper management position up to this day. His reign of terror lasted from 2009 to 2013, but his timeless tale is stuff of legend which is going to last forever.

Despite being the sole benchmark for his crazy roster moves, there is nothing that can compare to the crazier reasons behind them.

We can partially blame Glen Taylor for handing the reigns over to someone who clearly lacks NBA executive experience, but as a former NBA sports writer and a person who is familiar with movement in the league, it would be safe to assume that he would get better progressively.

Warriors, Stephen Curry, Timberwolves

The 2009 NBA draft will notoriously be known as a preview of things to come. Armed with four first round picks, two in the top ten, a splash was needed for an underwhelming 24-58 the season prior.

With the 4th and the 5th pick they selected two point guards in Ricky Rubio and Jonny Flynn, which was confusing choice both being non-shooters which would pose a positional problem. Moreover, they completely whiffed on the talent available with the likes of Stephen Curry, DeMar DeRozan, and Jordan Hill who were still on the board that time.

In the same Kahn-like manner, the 2010 draft was a step back for the Timberwolves. They took a 23-year-old athletic prospect with decent three-point range, Wesley Johnson was the 4th overall pick. DeMarcus Cousins, Gordon Hayward, and Paul George were some of the names picked after him.

paul george

Kahn was also in the business of trying to redeem former lottery talents, namingly Michael Beasley and Darko Milicic. The former was a logical move as Beasley fell out of the rotation while averaging 14.8 rebounds and 6.4 rebounds during the 2010 season.

While the same cannot be said about the latter, it was one of Kahn’s delusions that senselessly dubbed him that he could be one of the top centers in the league.

Kevin Love could’ve been locked with the Timberwolves till 2017?! Apparently, Kahn did not think the All-star was good enough to garner a five-year max contract. They signed him up for four with a player option for the third, making him a free agent for 2015.

His four-year tenure was arguably the worst in NBA history. The Timberwolves went 89-223 during that span.

Hiring Isiah Thomas

As a basketball player, his Hall of Fame career boasts of 12-time All-star appearances, five-time All-NBA selections, a Finals MVP, and two NBA championships, a feat worthy of Isiah Thomas’ legend.

However, that kind of Hall of Fame success did not necessarily translate into success off the court. Regrettably, success is the last word that would ever come to mind regarding Isiah Thomas the executive.

James Dolan, Knicks

Thomas’ starting gig as an NBA executive wasn’t too bad. The first GM of the Toronto Raptors, he had some pretty good picks in Tracy McGrady, Marcus Camby, and Damon Stoudemire. There was potentially a bright future in the North.

Consequently, Thomas had other plans for the future of the Raptors. He tried to make a power play with his ownership stake in the team. With his nine percent stake and discontent, he tried to usurp power and pull some strings to be the team’s majority owner. Once it failed in 1997, he sold his stake and bailed on his GM obligations.

The team had a hard time to bounce back with damage he had done. Starting disastrously with 1-19 and ending the season with 16 wins, it seemed that the franchise was doomed.

James Dolan, Kristaps Porzingis, Frank Ntilikina, Tim Hardaway Jr.

His departure was a stroke of luck for the Raptors. Despite the rebuild in his absence, they made the playoffs three straight years from 2000-02. They never made the playoffs in Thomas’ tenure.

The fabled lore of his countless fiascoes were just beginning.

After his shot at GM, he got his first coaching gig as the head coach of an early 2000s Pacers team. A powerhouse in the East with the likes of ace shooter Reggie Miller, a prime Jermaine O’Neal, and a legitimate scoring threat in Jalen Rose.

jalen rose, draymond green, charles barkley

A perfect scenario for Thomas, this was the same team which was ripe for the picking coming from a playoff Finals showdown with the mighty Lakers. Taking the coaching reigns from a then-tired Larry Bird, this was something too good to be messed up.

In Thomas-like fashion, he miraculously messed things up. While they did manage to make the playoffs in the first two years of his coaching as the eighth seed, his inexperience was evident and led to their downfall.

Although they managed to be third in his final year with a 48-34, it still was not enough for them to overcome their playoff matchup with the Celtics. In his three years as head coach, they never managed to squeak out the first round. Upon his departure, the Pacers were back to its winning ways. The 2004 season with Rick Carlisle now at the helm, they got to 61-21 for the number one seed in the East.

Isiah Thomas, Spencer Haywood

The thought of Thomas screwing up a team’s potential success is cringeworthy. For all those years lost, he was the biggest mistake the Pacers never really saw coming.

If you thought things could not get any worse, Isaiah Thomas just manages to surpass those expectations.

He took over the Knicks GM job in 2003 and added head coach to his list of responsibilities on 2007. He was completely relieved of all his duties on 2009.

During his administration, he drafted some pretty good talent in David Lee, Trevor Ariza, and Wilson Chandler. He had an undaunted track record for impressive draft acquisitions, but were completely irrelevant due to him single-handedly tanking the Knicks.

isiah thomas

To this very day, the questionable trade for underwhelming Bulls center Eddy Curry for two unprotected first round picks will be the very definition of his tenure. Unnoticed by most, he screwed over the Knicks finances by the end of the 2006 season by having the league’s highest salary with nearly $120 million for paying an underwhelming 23-59 team.

Aside from his tragic basketball moves, his off the court battle with sexual harassment charges made it worse than it should be. 2007, a jury found the Knicks general manager and head coach liable for aiding and initiating in sexual and verbal abuses of a fellow female executive.

Thomas insists and claims that he is innocent.

James Dolan, Kristaps Porzingis, Frank Ntilikina, Tim Hardaway Jr.

Despite the media circus and the embarrassment, Thomas survives this and manages to still be on top of basketball operations for the Knicks after the controversy.

To sum things up, Thomas spent a lot of the team’s money, sunk the roster, lost a ton of games, and got tolerated with everything that he did.

Lakers trading Shaq

The Los Angeles Lakers emerged as a dominant force in the NBA once again during the early 2000s. With the one-two punch of Laker duo Shaquille O’Neal and Kobe Bryant plus the tutelage of the legendary Phil Jackson, a dynasty was born in Hollywood.

At the center of the brewing success, a feud was about to stir things up for the Lakers.

Grant Hill, Shaquille O'Neal

Two of the most well-documented personalities in league history, Shaq and Kobe were on a league of their own. No force in the league could stop the duo during that time.

Shaq was the more candid one. A jokester and an entertainer by heart, his rare combination of talent, physical gifts, and theatrics was rarely rivaled in the league. His size made it impossible for his supremacy to go unnoticed.

On the other end, Kobe was the more cerebral of the two. Born with a Jordan-like domineering personality, he strives to be the best in any scenario. With an insatiable hunger for success, it was clear Kobe wanted to be alpha.

Despite the differences in personality, they managed to win three NBA titles from 2000-2002.

Kobe Bryant, Shaquille O'Neal


Things went south at the start of 2003 as O’Neal seemingly went to camp overweight and out of shape. Paired with toe and foot injuries, it was not a good combination for the once dominant giant. However, Bryant took the situation negatively as he saw O’Neal lazy and uncommitted.

The situation was all that Bryant needed to get out of Shaq’s shadow. He flourished and the offense ran mostly through him. Despite the controversies and verbal jabs between the two, it did not stop the Lakers from reaching the playoffs.

Unsurprisingly, the Lakers lost to fellow western powerhouse the San Antonio Spurs in the same year. The year after, their trip to the Finals was cut short in 5 games by the defensively elite Detroit Pistons for the championship.



In the summer of 2004, the drama escalated to an all-time high, which saw Shaquille O’Neal shipped to the Miami Heat for Caron Butler, Lamar Odom, Brian Grant, and a future first rounder.

As a result, Shaq won his fourth ring in 2006 as he played sidekick to Heat star, Dwyane Wade, while Kobe brought the Lakers back to its winning ways in 2008-2010 by nabbing two consecutive championships.

Looking back, a duo that dominant should have been nurtured and cultivated by the organization. The NBA is clearly a player driven league, but for the success of the franchise, things should not go spiraling as easy as it should have been.

Shaquille O'Neal

If they diffused and managed the situation in a manner that would’ve made O’Neal and Bryant stick together the results would have been historic. If they stuck it out for three years more, a six-peat could have been in the conversation.

At 33-years-old, Shaq still had enough left in the tank to power it out with Wade. Imagining a prime Kobe instead of Wade would have made a case for the most dominant duo ever in NBA history.

Shame on Mitch Kupchak for robbing the league of the greatest thing that could have been and the possible greatest streak of championships in NBA history. Regrettable not only for the Lakers, but for the entire league without a doubt.

kobe bryant, shaquille o'neal

The Worst NBA trade ever

When Russian billionaire Mikhail Prokhorov bought the then-New Jersey Nets, it must have felt like one step towards world domination.

Never the one to lack confidence, he audaciously claimed a comeback of epic proportions under his ownership. From being a league cellar-dweller, to a playoff team in one season, to a championship in no longer than five years, the Russian Oligarch went all in as they were moving the franchise to Brooklyn.

Just like that, from new ownership to win now mode instantly, quick fixes would be the underlying tone of the Nets for years to come.

Mikhail Prokhorov, Joe Tsai

Three-time All-star and two-time All-NBA, during his heyday Deron Williams was a shoe-in for the conversation of resident Point God in the league. It was no surprise that the Brooklyn Nets went for the then-26-year-old dynamic point guard during his prime.

Derrick Favors, Devin Harris, two first rounders, and cash were sent to the Jazz in 2011 for his services. It seemed like the Prokhorov’s declaration would come to come to fruition, a glimmer of hope for the Nets faithful.

Accelerating the process, the Nets went all out for former Atlanta All-star Joe Johnson the year after. A five-man trade along with a first and second rounder was enough to pry him away from the Atlanta franchise.

paul pierce

The Brooklyn based franchise had its first taste of playoff action in 2013 against a tenacious Chicago Bulls team. They got dropped in the first round in seven games.

Having a successful enough season prior, 2014 was the year they totally broke the bank for the sake of winning. The Nets took a chance on high profile rookie coach and Hall of Fame point guard, Jason Kidd. Furthermore, the franchise believed that they needed more established players to compliment the trio of Williams, Johnson, and Brook Lopez.

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In a desperate attempt to do just that, they cleared their cupboard for five players and three first rounders which they sent to Boston for two future Hall of Famers, Kevin Garnett and Paul Pierce, along with Jason Terry and DJ White.

Kevin Garnett

A bold playoff chasing move, it would have also been brilliant if Garnett weren’t 37 and Pierce 36-years-old during that time. The payroll that ballooned to more than $120 million was more than enough to be half-hearted on the roster overhaul.

Nonetheless, the championship promise looked viable this time.

The 44-38 Nets were good enough for sixth seed in the weaker Eastern conference. Squeaking by 4-3 to the Raptors, they advanced to the Semifinals. Unfortunately, they could not get past an overwhelming Miami Big 3 led by LeBron James.

After head coach Jason Kidd took the bullet and was fired for the underwhelming playoff run, they managed a first round exit versus the Hawks the year after. Stuck in limbo without their picks, the roster was gutted for spare parts in 2016.

charles barkley, kevin garnett

This time in Nets history serves as a cautionary tale of broken promises, senseless win-now aspirations, and improper knowledge of running an NBA team.

The saddest part are the unprotected picks that turned out to be James Young, Jaylen Brown, and Jayson Tatum. Thanks to the Nets, the Celtics are contenders and now have an amazing pool of talent at their disposal.

Regrettably, spending an absurd number of millions of dollars won’t get you an NBA championship, but it can get you invested in an underwhelming washed up roster that will lock your future in debt. To player salaries, luxury taxes, and lost picks, if they could, they would definitely go back in a heartbeat.

Two minutes too late

derrick rose, jabari parker

The post-Jordan Chicago Bulls were a mediocre bunch to watch. Not too bad, but not too good either, with no real star power to keep you glued, their relevance was fading in the league.

A Chicago kid named Derrick Rose changed all that. The 1st overall pick of the 2008 NBA draft was a real athletic specimen. He may not have the three-point stroke like most guards do, but his otherworldly speed and athleticism made him an unstoppable slasher to the basket.

The 2009 Rookie of the Year, a three-time All-star, an All-NBA selection, and a season MVP, Rose was on his way to be one of the all-time greats. He averaged 25 points, 4.1 rebounds, 7.7 assists, and 1 steal in his lone MVP season. He was the youngest player to win at 22-year-old.

Derrick Rose

His MVP brilliance fell short to Miami’s mighty Big 3 in the Eastern Conference Finals of 2011 Playoffs. Despite the setback, the Bulls were primed to be contenders once more with Rose at the helm.

2012 would dictate a different story for Rose and the Bulls. They had their best season in a long time, finishing 50-16. Headed to the playoffs they were the top seeded team. A dangerous Sixer team led by Andre Iguodala and Elton Brand were primed for an upset.

Game 1 of the series ended in tragedy for the Bulls. Although they won the opener, they lost Rose on a torn ACL with less than two minutes in the game. His knee gave out on a landing.

Derrick Rose


The Bulls were up 99-87, it was a questionable call leaving him in the game knowing they had a decent lead to cruise on. Bulls head coach Tom Thibodeau who called the shots, was known around the league to heavily lean on his top players to grind the games out.

Aside from losing the series to the Sixers, the real gut punch was the injury of Rose who the league saw as a fast rising star, came crashing to earth in an instant. Even with his rehabilitation and comeback, the explosive and dominant Derrick Rose was a mere shell of himself.

Along with his injury, Rose brought the championship hopes and dreams of Chicago with him. Fans can only dream of the possibilities of what a healthy Rose can do.

Derrick Rose


Although he was already battling injuries early in the season, the regret of making those small cumulative decisions that added to the wear and tear to his knees, those must have haunted the team thinking about those possible championships.

If they focused more on the preservation or longevity of Rose’s production than the maximum output that he could dish out, we might have seen more greatness from the former Bull.