Every NBA Team's Most Regretful Trade

NBA teams can change their franchise forever with a big trade. Many teams to win the NBA Championship have either made a huge trade to gain a Superstar or a minor one to find a missing piece. The Houston Rockets acquired NBA legend Clyde Drexler towards the end of his prime to win the 1995 NBA Championship. The Cleveland Cavaliers recently trading for Kevin Love and formed a new big three that helped the franchise win their first title. Big moves can truly change the landscape of a franchise. Those two examples show how much success can come from a good trade.

The opposite side of this features negative moves that damage the short term and long term of a franchise. A bad trade can truly sink a team for many years as we'll look at with the following deals. These specific deals are remembered in heartbreaking fashion for fans of these franchises. Every team has made various bad moves due to the nature of basketball being predictable. These however stand out as the worst of the worst. We'll take a look at each specific franchise’s most regrettable trade in team history that still haunts the fan base to this very day.

30 Atlanta Hawks: Trading away Bill Russell

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Bill Russell will always be remembered as one of the greatest winners in NBA history. The center won a shocking eleven NBA Championships with the Boston Celtics. Boston however had to trade for the future legend following the 1956 NBA Draft. The St. Louis Hawks (now Atlanta Hawks) traded Russell after drafting him in exchange for Ed Macauley and Cliff Hagan.

Russell went on to dominant the NBA with the Celtics dynasty and is still a beloved figure in the game. The Hawks missed out on a potential legend rocking their uniform. Russell may not have won as many rings outside of Boston, but he still would have been a great player. Talent like that being sent away will always provide regret for a franchise. Atlanta fans could only wish to see Russell’s retired jersey and presence in the franchise today.

29 Boston Celtics: Trading away Joe Johnson

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The Boston Celtics have benefited from many trades in their storied history. The franchise’s worst trades are often minor but one clearly showed poor judgment. Boston traded Joe Johnson during his rookie season to the Phoenix Suns in exchange for Tony Delk and Rodney Rogers. The two role players did very little to improve the Celtics and Johnson went on to become a Superstar.

Many people overlook the success of Johnson during his time on the Suns, Atlanta Hawks and Brooklyn Nets, but the incredible seven All-Star appearances says it all. Johnson would have been an even bigger star playing for a high profile franchise like Boston. This isn’t a trade that haunts the Celtics given their success. It still is the worst move they’ve ever made by giving up a future star for nothing.

28 Brooklyn Nets: Trading for Kevin Garnett and Paul Pierce

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The worst trade in recent memory featured the Brooklyn Nets completely ruining their franchise. Brooklyn desperately wanted to make an impact by contending for a title. The Nets made a massive trade acquiring veterans Kevin Garnett and Paul Pierce to form an impressive starting lineup with fellow former All-Stars Joe Johnson, Deron Williams and Brook Lopez.

Lopez suffered a season ending injury and the Nets were disappointed by the aging of Garnett and Pierce. Brooklyn sadly gave up three unprotected first round picks and the right to swap this recent draft pick. The Nets ended up winning the draft lottery sending the top overall pick to the Celtics. It will take quite some time for Brooklyn to be a playoff team again thanks to the long term effects of this trade.

27 Charlotte Hornets: Trading away Kobe Bryant

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Kobe Bryant has been a Los Angeles Laker for the entirety of his NBA career, but they weren’t the team to actually draft him. The Charlotte Hornets selected Bryant with the 13th overall pick in the 1996 NBA Draft out of high school. Charlotte wasn’t sold on the idea of having a player with no college experience on their team and specifically drafted him for trade purposes.

The Lakers sent center Vlade Divac in exchange for Bryant. Divac was a very good center but had nowhere near the talent or potential of Kobe. To make matters worse, Divac left the Hornets after a few seasons to join the Sacramento Kings. Bryant went on to become an iconic player and the second best shooting guard in the history of the NBA after Michael Jordan.

26 Chicago Bulls: Trading away LaMarcus Aldridge

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The Chicago Bulls have made a few terrible moves following the Michael Jordan era as they looked to become a contender again. One horrible mistake featured them trading away an extremely talented rookie. Chicago drafted LaMarcus Aldridge with the second overall pick in the 1996 NBA Draft. Aldridge however ended up on the Portland Trail Blazers his rookie season due to the horrible trade.

Chicago missed out on a top tier power forward and returned the combination of Tyrus Thomas and Viktor Khryap in return. If you know what Thomas and Khyrap are doing today, you're a better basketball fan than 99.9% of the world. The Bulls could have had their next big star with Aldridge but instead received two busts in return.

25 Cleveland Cavaliers: Losing out on James Worthy

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Another all-time terrible trade that revolved around draft night featured the Cleveland Cavaliers missing out on James Worthy. Cleveland gave up their first round pick in the 1982 NBA Draft along with a few other assets to the Los Angeles Lakers for the services of Don Ford. The pick that the Cavaliers traded away ended up being the first overall pick of Worthy.

The Lakers once again caught a huge break by drafting a future Hall of Famer. Worthy spent his entire career in Los Angeles racking up the accomplishments. Seven All-Star appearances, three NBA Championship wins and one NBA Finals MVP perfectly sums up the greatness of Worthy. Cleveland could have had the superb play of Worthy for their franchise if not for overestimating the value of Ford.

24 Dallas Mavericks: Trading away Jamal Mashburn

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This may be a surprising pick for the worst trade in Dallas Mavericks history due to the popular belief of it being the loss of Jason Kidd. The Kidd trade actually saw them receive Michael Finley in return. Finley was a great Mavericks star that helped contribute to much success. The true worst trade saw Dallas send impressive scorer Jamal Mashburn to the Miami Heat for Sasha Danilovic, Kurt Thomas and Martin Muursepp.

Mashburn had a highly underrated career and contributed to the success of multiple teams. Sure, he wasn’t a Superstar but his presence would have helped the franchise find success before the Dirk Nowitzki era saved them. The names the Mavericks got back in exchange for Mashburn is absolutely embarrassing and a terrible trade they regretted.

23 Denver Nuggets: Trading away Carmelo Anthony

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Every NBA team needs at least one Superstar to contend. The Denver Nuggets had their man with playoff appearances every season during Carmelo Anthony’s tenure on the team. Anthony even led them to the Western Conference Finals before falling short to the Los Angeles Lakers. The talent of Anthony was obvious but his attitude saw him become a pain to deal with.

Denver and Anthony both mutually agreed it was best to trade him. The problem is the Nuggets got very little back when sending the star to the New York Knicks. Denver got Wilson Chandler, Raymond Felton, Danilo Gallinari, Timofey Mozgov and draft picks. It looks fine on paper due to the number of players but the franchise suffered for it. Many years later and the Nuggets are still trying to find a star for the future.

22 Detroit Pistons: Trading Chauncey Billups for Allen Iverson

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The 2004 NBA Championship run of the Detroit Pistons is one of the most shocking title wins in NBA history. Chauncey Billups was the leader of that team and became the face of the franchise leading them to playoff success for many years. Detroit made a shocking move in 2008 when dealing the beloved Billups and Antonio McDyess to the Denver Nuggets for Allen Iverson.

The Pistons hoped Iverson still had Superstar years left in him but instead saw a decline. Iverson could still score but it just didn’t lead to winning any longer. Billups found more success in Denver helping take the team to the Western Conference Finals. The fact that Billups played with such heart and led the franchise to their most recent ring just hurt the fan base’s desire to support the team. The Pistons have been an afterthought ever since the trade.

21 Golden State Warriors: Trading away Wilt Chamberlain

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The Golden State Warriors have the most dominant team in NBA history today, but they once actually sent away the most dominant player in league history. Center Wilt Chamberlain spent a few years on the Philadelphia/San Francisco Warriors putting up iconic numbers on a yearly basis. The Warriors made the foolish decision to trade him to the 76ers in exchange for Connie Dierking, Paul Neumann and Lee Shafer.

Chamberlain scoring a record breaking 100 points in a single game wasn’t enough to earn the loyalty of the Warriors. The career of Wilt would only improve as he's still viewed as one of the all-time greats. Warriors fans are clearly over it today with their potential dynasty. It still doesn’t erase the fact that the franchise actually traded away Wilt Chamberlain for little in return.

20 Houston Rockets: Trading away Moses Malone

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Moses Malone is one of the most underrated NBA legends of all time with the numbers, reputation and winning all being in his favor. The Houston Rockets had Malone in their lineup but wanted to deal the center. Malone would get traded from Houston to the Philadelphia 76ers for Rodney McCray and Caldwell Jones.

The trade instantly flopped for the Rockets when Malone led the 76ers to a NBA Championship the next season. Malone continued to play well leading the league in rebounds per game over the following three years. Philadelphia fans still remember the good ol’ days of Malone leading the franchise. Houston would rebound by drafting Hakeem Olajuwon a few years later but they ditched a proven star for nothing in return. You can’t erase that no matter how successful you would be a little while later.

19 Indiana Pacers: Trading for Stephen Jackson

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A rare franchise worst trade came for the Indiana Pacers when they acquired Stephen Jackson. The trade actually was a talent upgrade as they just sent Al Harrington in exchange for Jackson’s services. Indiana however saw chemistry issues and many other negative changes come from the addition of Jackson. The memorable brawl in Detroit featured Jackson among other Pacers fighting with fans in one of the all-time low NBA moments.

Jackson’s attitude definitely changed the team for the worst and he played a huge role in the brawl. The Pacers would see their time as an Eastern Conference contender end here. Harrington was a better fit that helped the Pacers look like slight contenders for a ring. The decision to trade him for Jackson ended the positive momentum for a long time.

18 Los Angeles Clippers: Losing out on Kyrie Irving

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One of the worst instances of a franchise being cheap featured the Los Angeles Clippers making a franchise-worst trade under the ownership of Donald Sterling. The Clippers were desperate to unload the contract of veteran guard Baron Davis. Los Angeles traded Davis and an unprotected first round pick for Mo Williams and Jamario Moon. Williams and Moon went on to do nothing for the Clippers.

The bad luck reached a new peak when the Clippers actually won the draft lottery that year and were forced to send the top overall pick to the Cleveland Cavaliers. Cleveland selected Kyrie Irving with the pick. The talent of Irving helped bring LeBron James back to the Cavaliers and they won a championship together. Their luck has been better these past few years but moves like this made you wonder if the Clippers were cursed.

17 Los Angeles Lakers: Trading for Steve Nash

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The Los Angeles Lakers looked to form a new super team in 2012 by acquiring two Superstars. Los Angeles first acquired Dwight Howard and later Steve Nash. The Howard trade saw them give up very little in return calling it even. However, the deal for Nash ended up hurting the franchise. The Lakers sent four total draft picks to the Phoenix Suns in exchange for the Superstar point guard to join Howard and Kobe Bryant.

Nash sadly saw his body start to break down early into his Lakers career. Before the injuries, there was no chemistry on the Los Angeles super team and they struggled to even make the playoffs. Nash barely played for the rest of his career due to the injuries and the Lakers were forced to pay him to sit on the bench.

16 Memphis Grizzlies: Trading away Pau Gasol

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One trade that helped make the Los Angeles Lakers a super team was acquiring Pau Gasol in exchange for junk. The Memphis Grizzlies sent Gasol to form a new dynamic duo with Kobe Bryant for Kwame Brown, Javaris Crittenton, Aaron McKie and draft picks. Many people forgive the Grizzlies for making this trade due to the fact that one of the picks/rights transferred secured them Marc Gasol.

At this time, Marc was a second round draft pick and the Grizzlies only saw any value in him due to scouting him as the brother of Pau. They could have easily gotten more from any other team, including the Lakers. The Lakers won another two rings due to getting Pau without having to sacrifice any of their assets. You know a trade is awful when Kwame Brown is the biggest name on one side.

15 Miami Heat: Trading away Steve Smith

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The Miami Heat have been one of the better run franchises during their NBA existence. Their most regrettable trade was a forgettable one that sent talented shooting guard Steve Smith to the Atlanta Hawks along with Grant Long for Kevin Willis. Smith contributed greatly to the Hawks for the following five seasons averaging over 18 points.

Miami surely could have used Smith during their iconic battles with the New York Knicks during their bitter rivalry. The presence of Smith also would have improved their chances at contending when Alonzo Mourning and Tim Hardaway took the team to the next level. The Heat were one player away from truly making an impact in the Eastern Conference and that player could have been Smith to make up the difference.

14 Milwaukee Bucks: Trading away Kareem Abdul-Jabbar

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Everyone debates Michael Jordan, LeBron James and Kobe Bryant when it comes to who is truly the greatest NBA player of all time. The biggest snub from that conversation sparked from today’s generation is the legendary Kareem Abdul-Jabbar. Fans of the Milwaukee Bucks in the 1970s were treated to one NBA Championship with him. An unfortunate trade would rob them out of more.

Milwaukee traded Abdul-Jabbar to the Los Angeles Lakers for Elmore Smith, Brian Winters, David Meyers and Junior Bridgeman. Abdul-Jabbar led the Lakers to another five NBA Championship runs. The career of Abdul-Jabbar is remembered today for being the all-time leading scorer in franchise history. Kareem dominated the NBA during his time on the Lakers and you could see how great he was in Milwaukee. The Bucks sadly missed out on his greatness for the majority of his career.

13 Minnesota Timberwolves: Trading away Al Jefferson

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The Minnesota Timberwolves have at least been able to get good talent back in past Superstar trades losing Kevin Garnett and Kevin Love. One great talent they failed to benefit from moving was Al Jefferson. The center had a few great seasons of tremendous offensive play. Many pundits expected the Timberwolves to get a great star or multiple young prospects in a trade.

Minnesota only received Kosta Koufos and a couple of forgettable draft picks from the Utah Jazz in exchange for the talented center. Timberwolves fans aren’t too upset due to the play of Jefferson diminishing shortly after leaving the franchise. It's still a regrettable trade given the value Jefferson held during his tenure in Minnesota. The Timberwolves took a very weak offer proving they just wanted to move on to new talent.

12 New Orleans Pelicans: Trading away Chris Paul

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Chris Paul is one of the top Superstars of his era. You’ll be hard pressed to find many point guards with an overall career with as many great years as Paul. The New Orleans Hornets/Pelicans realized Paul was no longer happy and looked for a trade partner.

Los Angeles Lakers fans were ecstatic about the rumored trade of Paul joining them in exchange for Kevin Martin, Luis Scola, Lamar Odom, Goran Dragic and a first-round pick. David Stern and NBA officials shut the deal down claiming it was unfair. New Orleans instead traded Paul to the Los Angeles Clippers for Eric Gordon, Chris Kaman, Al-Farouq Aminu and a first round pick. They received nothing relevant from the three players and the trade ended up being a bust for such a star. The Lakers trade at least offered future star Dragic and then star Odom.

11 New York Knicks: Trading away Patrick Ewing

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Some trades hurt a franchise beyond the court or contending for a title. The New York Knicks have made many atrocious trades over the past two decades but the worst one featured the franchise turning their back on a beloved legend. Patrick Ewing carried the Knicks during his tenure there from the late 80s through the 90s.

Knicks fans grew to adore him as the man they associated with the blue and orange. New York traded Ewing to the Seattle Super Sonics receiving the trio of Luc Longley, Glen Rice and Travis Knight. None of the three improved the Knicks and fans missed the aging Ewing. The franchise has been hated by the fans since the Ewing trade. It all started with the disrespecting treatment of a franchise icon for a pointless trade.

10 Oklahoma City Thunder: Trading away James Harden

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The Oklahoma City Thunder drafted one of the greatest cores of four top stars. Kevin Durant, Russell Westbrook, James Harden and Serge Ibaka all spent their first few years in the NBA together. They made the 2012 NBA Finals before falling short to the Miami Heat. Oklahoma City then realized they didn’t want to sign all four to max contracts.

Harden would be the odd man with a premature trade one season before he hit the free agent market. The Thunder sent Harden to the Houston Rockets for Kevin Martin, Jeremy Lamb and draft picks. No one would help Oklahoma City improve and they never returned to the NBA Finals. Harden took the next step forward after the trade. If the Thunder kept Harden and paid the big four, they likely would have won multiple times by now and Durant would have never left to form his own big four in Golden State.

9 Orlando Magic: Serge Ibaka

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Former Oklahoma City Thunder Serge Ibaka was the second of the four to get traded. The Orlando Magic acquired Ibaka by giving up Victor Oladipo and Domantas Sabonis. Neither Oladipo nor Sabonis have been great for the Thunder and Ibaka is a very good power forward. The trade could have worked out in their favor but another bad decision ended it.

Orlando traded Ibaka less than one season into his tenure. The Magic sent Ibaka to the Toronto Raptors for Terrence Ross and a first round pick. There was no point to the original trade giving up their two young assets. Orlando has no clue what they're doing. The two trades acquiring and then giving up Ibaka completely embarrassed them. Free agents will not be lining up to join this franchise looking at their recent track record.

8 Philadelphia 76ers: Trading away Charles Barkley

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Charles Barkley is arguably the greatest power forward of all time. The Philadelphia 76ers enjoyed his talent for many years before the star requested a trade. Barkley wanted to find a better team forcing Philadelphia’s hand. Sadly, the 76ers did not make the most of Barkley’s value. You have to get a star or multiple assets back when dealing such a Superstar.

Philadelphia only received Jeff Hornacek, Tim Perry and Andrew Lang back in return for their top name in a trade with the Phoenix Suns. Barkley added to his legacy in Phoenix by getting to the NBA Finals before falling short to Michael Jordan. The 76ers struggled for many years following this trade until drafting Allen Iverson. Barkley being traded away for little to nothing remains the most regrettable trade in Philadelphia franchise history.

7 Phoenix Suns: Trading away Isaiah Thomas

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Isaiah Thomas is one of the most underappreciated stars in recent NBA history. The talent and production of Thomas have shown just how great he is. Multiple teams have however failed him due to not believing in the player. Thomas being one of the shortest stars in the NBA led to teams thinking he would not have a long term future.

The Phoenix Suns completely dropped the ball by believing this. Phoenix traded Thomas to the Boston Celtics in exchange for Marcus Thornton and an irrelevant draft pick. Thomas went on to become a Superstar in Boston leading the franchise to the best record in the Eastern Conference. The Suns have been one of the worst teams in the NBA since then. You have to laugh at them for disrespecting Thomas by trading him for nothing.

6 Portland Trail Blazers: Trading away Clyde Drexler

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A franchise trading away veteran players to contenders is a nice gesture but you should get something good in return. The Portland Trail Blazers learned this the hard way when the legendary Clyde Drexler wanted to be traded in 1995. Drexler would get dealt to the Houston Rockets in exchange for Otis Thorpe and late round draft picks.

Houston went on to win their second consecutive NBA Championship. Drexler played a few more seasons for the Rockets contributing to their success. Portland struggled to find relevance for a couple of years. The fact that they got nothing back for one of their few stars was a huge mistake. It was still very respectful of them to give their former face of the franchise an opportunity to end his career on his own terms. Sadly, they got nothing for it.

5 Sacramento Kings: Trading away Isaiah Thomas

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Isaiah Thomas is on this list for a second time as franchises just don’t appreciate him. The Sacramento Kings struck gold when drafting Thomas with the last overall pick in the second round of the 2011 NBA Draft. Thomas delivered three great seasons for the Kings and averaged 20.3 points before getting traded away unceremoniously. All Sacramento wanted in return for the dynamic scorer was Alex Oriakhi and a trade exception.

The Kings have been a complete disaster and badly need a point guard. Thomas has to be laughing witnessing their failures as he shines as an All-Star today. Sacramento recently trading away DeMarcus Cousins could top this, but time will tell. As of now, losing one of the premiere point guards due to poor judgment is the worst move they’ve pulled off.

4 San Antonio Spurs: Trading away Dennis Rodman

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The San Antonio Spurs have very few poor trades in their history. One regretful trade that stands out featured them trading Dennis Rodman to the Chicago Bulls for Will Perdue. Rodman’s incredible rebounding and dominant defense helped the Bulls three-peat in the late 90s. San Antonio dealt Rodman because they could not put up with his poor attitude.

Kenny Smith recently stated on an episode of NBA Open Court that his Houston Rockets team had a celebration when they found out the Spurs traded Rodman. The Rockets believed Rodman on the Spurs made them the biggest threat in the West. San Antonio may have made an NBA Finals appearance earlier than their eventual dominant years. It still all worked out and no Spurs fan can ever complain.

3 Toronto Raptors: Trading away Vince Carter

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Vince Carter became the face of basketball in Canada as the first Superstar on the new Toronto Raptors franchise. The incredible scoring, highlight dunks and must-see style of play made Carter a household name. Unfortunately, the relationship between Carter and the Raptors started to sour. A trade was obvious but you expected Toronto to get a great haul for such a star.

The New Jersey Nets acquired Carter by sending Alonzo Mourning, Eric Williams, Aaron Williams and draft picks to the Raptors. Mourning never reported to Toronto and none of the other names did anything of note. Carter went on to have many more impressive seasons with the Nets and other teams. Raptors fans have hated him to this very day partly due to how poorly they did in the trade.

2 Utah Jazz: Trading away Enes Kanter

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The Utah Jazz strangely have not been involved in many poor high profile trades. A regretful one revolves around ditching the talent and youth of big man Enes Kanter. Utah sent Kanter to the Oklahoma City Thunder in return for Grant Jerrett, Kendrick Perkins, Tibor Pleiss and a draft pick. Basically, they gave away a valuable asset for absolutely nothing.

Kanter is still a member of the Thunder as they hope to make him one of the top players to build around as a support system for Russell Westbrook. The Jazz have rebounded to become an impressive team in the Western Conference. They still could be in a better place if they managed to get something of note back for Kanter. Gordon Hayward’s free agency will make every Utah fan question the franchise’s poor moves.

1 Washington Wizards: Trading away Chris Webber

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Chris Webber is underappreciated when discussing the great power forwards in NBA history. The talent and results of Webber have led to a potential Hall of Fame worthy career. The Washington Wizards actually had Webber as he entered his prime. At the age of 25, they made the horrible decision to trade him to the Sacramento Kings for an aging Mitch Richmond and Otis Thorpe.

Washington continued to be a joke and Webber led the Kings to title contention. If not for crooked referees in 2002, Webber may very well be a NBA Champion and NBA Finals MVP today. The Wizards gave it all up for two guys that you barely remember even played for them. It's difficult to find a trade that looked as bad at the time as it still does today.

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