Every NBA Team's Biggest Mistake of the Last 20 Years

Greg Swartz@@CavsGregBRCleveland Cavaliers Lead WriterMay 28, 2020

Every NBA Team's Biggest Mistake of the Last 20 Years

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    Everybody makes mistakes, even (especially?) NBA front offices.

    From failed draft picks to trades gone wrong, missteps can end up crippling franchises for years. Bloated contracts and passing on eventual stars on draft night have haunted teams as well.

    Since 2000, these are the biggest mistakes every NBA team has made.   

Atlanta Hawks: Signing Joe Johnson to $124 Million Deal

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    The summer of 2010 featured one of the most star-studded free-agent classes in NBA history.

    Even with LeBron James, Dwyane Wade, Chris Bosh, Dirk Nowitzki, Amar'e Stoudemire, Paul Pierce, Ray Allen and Rudy Gay signing new deals, it was Joe Johnson who came away with the largest contract.

    His six-year, $124 million deal to stay with the Atlanta Hawks was roughly $14 million more than James' six-year contract with the Miami Heat. The salary cap for the 2010-11 season was just $58 million, meaning Johnson's deal then would be the equivalent of a six-year, $234 million contract today.

    While Johnson was coming off five straight seasons of averaging 20-plus points, he'd never again reach that mark after signing his megadeal.

    Just two seasons in, the Hawks traded Johnson to the Brooklyn Nets in a salary dump that also netted them a 2013 first-round pick.

    Johnson spent three-and-a-half seasons with the Nets before being waived in February 2016, making over $20 million in the last year of his deal.     

Boston Celtics: The Kyrie Irving Experience

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    The Kyrie Irving trade in 2017 initially seemed like a home run for the Boston Celtics.

    Irving was just 25 years old, coming off a season in which he averaged 25.2 points and 5.8 assists per game and still had two guaranteed years remaining on a five-year, $94.3 million contract (2019-20 player option). Getting him off the Cleveland Cavaliers meant severely damaging the Celtics' biggest threat in the Eastern Conference as well.

    Boston was on the rise with Al Horford, Jaylen Brown, Marcus Smart, Avery Bradley and Terry Rozier, and it had just selected Duke forward Jayson Tatum No. 3 overall. Point guard Isaiah Thomas had a serious hip injury, with his date to return for the 2017-18 season unclear. Losing Thomas to a major injury would kill the team's momentum.

    In the end, the Celtics gave up Thomas, Jae Crowder, Ante Zizic, an unprotected 2018 first-round pick from the Nets and a 2020 second-round pick for Irving. Thomas and Crowder were valuable starters, and the Brooklyn selection had real potential to be No. 1 overall. But Boston was loaded with draft picks, and it looked like Irving could help them win right away.

    While Thomas' hip injury made it necessary for the C's to find a new point guard, Irving's time in Boston was a disaster. Injuries forced him to miss the entire 2018 postseason, and his verbal commitment to re-sign with the Celtics quickly deteriorated as he called out the team's young players and split up the locker room.

    Irving left as an unrestricted free agent in 2019, while the Cavaliers used the Nets pick to select Collin Sexton. Cleveland later traded Thomas and Crowder in deals that would help land Kevin Porter Jr. and Larry Nance Jr.

    The Celtics would replace Irving with Kemba Walker in free agency, but losing Thomas, Crowder, Zizic and two draft picks for just one postseason run with Irving hurt.   

Brooklyn Nets: Trading for Paul Pierce, Kevin Garnett

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    Perhaps the worst trade of the millennium, the Nets went all-in in 2013, wanting to pair Kevin Garnett and Paul Pierce with Deron Williams, Joe Johnson and Brook Lopez.

    The Celtics sent a package of Garnett, Pierce, Jason Terry, DJ White, a 2017 first-round pick and a 2017 second-rounder for Gerald Wallace, Kris Humphries, Keith Bogans, MarShon Brooks, Kris Joseph and a treasure trove of draft picks (unprotected first-round selections in 2014, 2016, 2017 and 2018).

    While the Nets didn't expect those first-rounders to be that valuable given their strong roster, they quickly fell apart given the ages of Pierce and Garnett.

    Pierce played just one season in Brooklyn at 36 years old, while Garnett lasted a year-and-a-half over his age-37 and 38 campaigns before the team traded him to the Minnesota Timberwolves.

    The picks Brooklyn traded began landing at the top of the draft, ending in the selections of Jaylen Brown, James Young, Markelle Fultz (by the Philadelphia 76ers in a pick swap that landed Jayson Tatum in Boston) and Collin Sexton (by the Cleveland Cavaliers in a trade that brought Kyrie Irving to the C's).

    Even making the picks top-three protected would have kept the Brown and Fultz selections in Brooklyn. While the 2017 first-rounder acquired by Brooklyn would turn into Kyle Kuzma, the Nets traded the pick to the Los Angeles Lakers with Lopez for D'Angelo Russell and Timofey Mozgov.

    The Nets have since done a fantastic job of rebuilding the franchise despite not having their own first-round picks to do so, but this was one of the worst trades of the past few decades.          

Charlotte Hornets: Paying Terry Rozier over Kemba Walker

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    While the Hornets organization has made some awful draft selections over the past 20 years (Adam Morrison, Frank Kaminsky, Noah Vonleh, Michael Kidd-Gilchrist, Malik Monk), the 2019 offseason was a critical turning point.

    Knowing that team icon Kemba Walker would command a major raise from his four-year, $48 million deal, Charlotte chose not to trade its best player before he hit unrestricted free agency.

    After making the All-NBA third team, Walker was eligible to sign a five-year, $221 million supermax deal. Walker was even willing to accept "slightly less" than the regular five-year, $190 million max to stay in North Carolina, according to Shams Charania of The Athletic.

    The Hornets offered neither. 

    Their best offer was for less than $160 million over five years, per Charania.

    It would have been better for Charlotte to watch Walker leave for nothing, but instead, it worked out a sign-and-trade with the Celtics to bring in backup point guard Terry Rozier on a three-year, $58 million deal.

    The Hornets didn't want to pay Walker $38 million a season, but they gave Rozier over $19 million. Walker was named an All-Star starter this season, while Charlotte has been 10.1 points per 100 possessions worse with Rozier on the floor.             

Chicago Bulls: Trading 2 First-Round Picks for Doug McDermott

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    Heading into the 2014 NBA draft with the Nos. 16 and 19 overall picks, the Bulls were targeting a shooter to add to their core of Derrick Rose, Joakim Noah, Jimmy Butler and Taj Gibson.

    Doug McDermott was one of the best players in men's college basketball, and Chicago didn't feel the Creighton product would be available at their draft spot.

    In order to move up, the Bulls traded both of their 2014 first-round picks and a 2015 second-rounder to the Denver Nuggets for the rights to McDermott at No. 11.

    The Nuggets used the two firsts to take Jusuf Nurkic and Gary Harris, while players like Nikola Jokic, Clint Capela, Spencer Dinwiddie, Joe Harris and Jordan Clarkson were still on the board.

    While Nurkic and Harris have become valuable starters for the Portland Trail Blazers and Nuggets, respectively, McDermott averaged just 8.2 points per game in two-and-half seasons in Chicago.

    His trade from the Bulls may have been even worse than the one bringing him in. In February 2017, Chicago sent McDermott, Gibson and a 2018 second-round pick that would later become Mitchell Robinson to the Oklahoma City Thunder for Cameron Payne, Anthony Morrow and Joffrey Lauvergne.

Cleveland Cavaliers: The Entire 2013 Offseason

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    It would be easy to say that drafting Anthony Bennett No. 1 overall in 2013 was the worst move that the Cleveland Cavaliers have made over the past 20 years, but everything about that offseason was a train wreck.

    Heading into the 2013-14 campaign with real playoff hope thanks to the rise of players like Kyrie Irving, Dion Waiters and Tristan Thompson, the Cavs made mistake after mistake—all the way from the draft, to free agency to their head coaching hire.

    Drafting Bennett was obviously a mistake. He missed all 15 field-goal attempts over his first four games before going 1-of-5 in his fifth. The power forward finished his rookie season averaging 4.2 points, 3.0 rebounds and 0.3 assists in 12.8 minutes per game before being traded to the Minnesota Timberwolves in the summer in a deal for Kevin Love.

    Bennett wasn't the only mistake, of course.

    Cleveland gave Mike Brown a five-year, $20 million deal to return to the team just three years after the organization had fired him. Brown's defense-first approach and lack of an offensive system stunted the growth of players like Irving, and Brown even advocated that the Cavs should trade their young star.

    According to ESPN's Brian Windhorst, the Cavaliers fired Brown after just one season partly because of fear that Irving wouldn't agree to a contract extension.

    Free agency was a disaster as well. Andrew Bynum and Earl Clark didn't even last a full season before being traded before the deadline. Jarrett Jack played just one year in Cleveland after signing a four-year, $25 million deal and was dumped in the summer of 2014 to clear salary-cap space for LeBron James.

    The Cavs even traded for Luol Deng and Spencer Hawes during the season in a feeble attempt to make the playoffs, a mission that ultimately failed before both veterans left the team in free agency that summer.  

Dallas Mavericks: Not Matching the Suns' Offer for Steve Nash

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    In 2004, Steve Nash faced the difficult decision of whether to stay with Dirk Nowtizki, Michael Finley, Josh Howard and the Dallas Mavericks or become the face of the Phoenix Suns.

    When the Suns gave him a six-year, $65 million contract offer, Nash asked if the Mavs would match. Dallas was offering a deal worth around $45 million, and Mavs owner Mark Cuban had concerns about the 30-year-old point guard's durability.

    Nash then agreed to join Phoenix, where he would spend the next eight seasons.

    During that time, he averaged 16.3 points, 10.9 assists and 3.4 rebounds while shooting 51.0 percent overall and 43.7 percent from three. He won back-to-back MVPs, led the NBA in assists five times and made six All-Star teams.

    In 2016, Cuban said not re-signing Nash was the biggest mistake he's made as team owner, as Nash and Nowitzki would have been one of the greatest duos in the league.

Denver Nuggets: Trading Donovan Mitchell to Jazz During 2017 Draft

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    As good as the Nuggets are with Nikola Jokic, Jamal Murray, Paul Millsap and Michael Porter Jr., imagine adding Donovan Mitchell to the mix.

    Denver drafted Mitchell with the No. 13 overall pick in 2017 before agreeing to trade him for power forward Trey Lyles and the No. 24 overall pick, Tyler Lydon.

    Although the Nuggets couldn't have known Mitchell would immediately become a star, the trade didn't make much sense at the time. Lyles averaged only 6.2 points on 36.2 percent shooting as a sophomore. The Nuggets should have demanded a better sweetener to drop back 11 spots in the first round.

    Mitchell arrived in Utah at the perfect time, as Gordon Hayward left for the Boston Celtics in free agency that summer. The Louisville product kept Utah in the playoff picture and has averaged 22.7 points, 4.1 rebounds, 4.0 assists and 1.3 steals in his first three seasons.

    Lyles backed up Millsap for two seasons in Denver before signing with the San Antonio Spurs last summer. Lydon logged only 96 minutes over two seasons with the Nuggets.

Detroit Pistons: Drafting Darko Milicic over Wade, Melo and Bosh

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    While the Pistons' trade for Blake Griffin may go down as one of their biggest mistakes of the past two decades, their selection of Darko Milicic back in 2003 is an even bigger blunder.

    The Cleveland Cavaliers took LeBron James, giving the Pistons their choice of Carmelo Anthony, Dwyane Wade or Chris Bosh. Anthony was the favorite fresh off his spectacular freshman season at Syracuse, where he won a national championship.

    Anthony claims the Pistons would have won two or three rings had they drafted him, although former Detroit center Ben Wallace says Anthony would have messed up team chemistry and they never would have won the title in 2003-04.

    Even if the Pistons were satisfied with their roster heading into the 2003 draft, they could have gotten a haul for the pick had they traded trade it.

    Milicic will forever be one of the NBA's greatest busts, especially since multiple future Hall of Famers were selected directly after him.

Golden State Warriors: Ostracizing Kevin Durant

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    The Golden State Warriors were nearly unstoppable with Kevin Durant, going 8-1 overall in back-to-back NBA Finals victories in 2016-17 and 2017-18 before injuries ultimately led to their downfall in 2018-19.

    With Durant's upcoming free agency looming over the team throughout the 2018-19 season, some of the Warriors did an awful job of making him want to come back.

    Whether it was Draymond Green calling Durant a "b---h" and daring him to leave in free agency or general manager Bob Myers awkwardly joking that he hadn't earned whatever contract he wanted like Stephen Curry had, the Warriors continually shot themselves in the foot when it came to making Durant happy.

    Durant later admitted that the altercation with Green factored into his leaving the Warriors for the Brooklyn Nets.

    "I mean, your teammate talks to you that way, you think about it a bit," Durant said on ESPN's First Take. "Like I said, we talked about it. But definitely, for sure [it was a factor]. I'm not going to lie about it."

    The Warriors likely would have been the favorites to win the Finals again this year with a healthy Durant, Klay Thompson, Curry and Green. Instead, they'll now count on Andrew Wiggins to take Durant's place.

Houston Rockets: Ryan Anderson's $80 Million Contract

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    Looking to continue their modernization of the NBA, the Rockets gave Ryan Anderson a four-year, $80 million contract in the summer of 2016.

    Keeping the floor spread for James Harden was important, and Anderson was one of the better stretch 4s in the league.

    Still, $20 million per year was a lot for someone who didn't do much more than stand and shoot. Anderson wasn't a good rebounder despite his 6'9" size, nor did he pass or defend much.

    His time in Houston lasted only two seasons, where he averaged 11.6 points on 42.3 percent shooting and 4.8 rebounds. In August 2018, the Rockets sent him to the Phoenix Suns in a swap of bad contracts for Brandon Knight, and the Suns later sent to the Miami Heat for Tyler Johnson.

    Miami eventually waived him in July 2019 and stretched the final season of his contract, spreading his guaranteed $15.6 million out over three years.

Indiana Pacers: Trading Kawhi Leonard for George Hill

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    By 2011, George Hill had become one of the NBA's better backup point guards for the San Antonio Spurs. He was a talented three-point shooter and defender who seemed to be ready for a starting role.

    Needing a point guard, the Indiana Pacers agreed to trade the 15th and 42nd picks along with the rights to Erazem Lorbek for Hill.

    With the 15th pick, San Antonio took San Diego State forward Kawhi Leonard.

    While Hill served as a quality starter for some good Pacers playoff teams, Leonard slowly developed into an All-Star, Defensive Player of the Year and Finals MVP. Bertans, whom the Spurs selected with the 42nd pick, spent three good years in San Antonio, shooting 40.4 percent from three in his 220 games.

    While Leonard and Paul George have since teamed up on the Los Angeles Clippers, the pair almost became teammates on the Pacers in 2011.

Los Angeles Clippers: Trading 1st-Rounder to Dump Baron Davis' Contract

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    Looking to get off the remaining two years and $28.8 million on Baron Davis' contract, the Los Angeles Clippers agreed to send the veteran guard and an unprotected first-round pick to the Cleveland Cavaliers for Mo Williams and Jamario Moon in February 2011.

    The Cavs needed all the draft picks they could get with LeBron James having left the summer before, and the Clippers' pick was projected to fall somewhere in the top 10.

    While the Cavaliers' pick had the second-best odds of landing at No. 1 overall, it ultimately fell to fourth. The Clippers had the eighth-best odds and only a 2.8 percent chance at winning the lottery, yet the basketball gods punished them for giving up a fully unprotected pick.

    The Cavs would take Kyrie Irving at No. 1 overall and use their amnesty provision on Davis, while the Clippers missed out on the opportunity to pair Irving with Blake Griffin and DeAndre Jordan.

Los Angeles Lakers: Not Fixing the Shaq-Kobe Relationship

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    Kobe Bryant and Shaquille O'Neal are one of the greatest duos in NBA history, yet they could have accomplished so much more.

    During their eight seasons as teammates, the Los Angeles Lakers made eight playoff trips, four Finals appearances and won three championships. While O'Neal led the way during the Lakers' three-peat, Bryant seemed poised to take over as the No. 1 option as O'Neal entered his 30s.

    However, an ongoing feud between the two superstars ended with O'Neal being traded to the Miami Heat in 2004 for Caron Butler, Lamar Odom, Briant Grant, a 2006 first-round pick and a 2007 second-round pick.
    While Odom would play a key role in the Lakers' titles in 2008-09 and 2009-10, the Lakers didn't get a true superstar in return for O'Neal and failed to even make the playoffs in the first season without him.

    In Miami, the Hall of Fame center transitioned into the role he was meant to play beside Bryant, helping Dwyane Wade and the Heat win a championship in 2005-06.

    Had Bryant and O'Neal stayed together for longer, they could have gone down in history as the greatest duo of all time.

Memphis Grizzlies: Drafting Hasheem Thabeet

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    The Memphis Grizzlies quickly came to regret signing Chandler Parsons to a four-year, $94 million contract in 2016 even after he had suffered multiple knee injuries. However, selecting Hasheem Thabeet with the second overall pick in 2009 was an even worse mistake.

    With Blake Griffin going No. 1 overall to the Los Angeles Clippers, the Grizzlies wound up passing on multiple future MVPs by taking Thabeet.

    A defensive force at UConn, the 7'3" center looked like he would at least be a capable rebounder and rim protector in the NBA. Instead, his lack of offensive game caused the Grizzlies to trade him in February 2011.

    Memphis ultimately passed on James Harden, Stephen Curry, Jrue Holiday and DeMar DeRozan, all of whom would have paired nicely with Mike Conley in the backcourt.

    The Grit-and-Grind Grizzlies would have looked far different with a player like Curry or Harden on board, and they might have won a title or two had they not erred during the 2009 draft.

Miami Heat: Selecting Michael Beasley over Kevin Love, Russell Westbrook

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    Like the Memphis Grizzlies, the Heat probably wish they had made a different choice with a No. 2 overall pick.

    Michael Beasley had a monster college season at Kansas State in 2007-08, averaging 26.2 points and 12.4 rebounds as a freshman. With Derrick Rose going No. 1 overall to the Chicago Bulls, Beasley looked like a natural choice for Miami.

    While Beasley wasn't bad—he averaged 14.3 points and 5.9 rebounds over his first two NBA seasonshe wasn't developing into the star the Heat had drafted him to be.

    The Heat wound up dumping him on the Minnesota Timberwolves for two second-round picks to carve out enough cap room for LeBron James and Chris Bosh in free agency.

    While it worked out for Miami regardless, imagine what a Big Four of James, Bosh, Dwyane Wade and either Kevin Love or Russell Westbrook would have looked like if the Heat found a way to make the money work.

Milwaukee Bucks: Drafting Jabari Parker over Joel Embiid

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    Joel Embiid and Giannis Antetokounmpo have both been All-Star starters for the past three seasons. They were almost teammates on the Milwaukee Bucks, too.

    The Bucks had the No. 2 overall pick in 2014, and Andrew Wiggins, Jabari Parker and Embiid were projected as the top three overall picks.

    Embiid looked like the most talented of the three, but he suffered a foot injury right before the draft. According to Bleacher Report's Yaron Weitzman, the Cleveland Cavaliers would have selected Embiid with the No. 1 overall pick had he been completely healthy.

    When the Cavs instead took Wiggins, the Bucks were left to choose between Parker and Embiid at No. 2.

    Parker seemed like the safe choice, as he was coming off a sensational freshman season at Duke, although Embiid had the higher upside. The Bucks went with Parker, although he wound up tearing his left ACL twice over the ensuing seasons. Milwaukee eventually let him walk in free agency as soon as his rookie contract expired.

    Embiid has shaken off a few major injuries to become arguably the best all-around center in the NBA. Combined with Antetokounmpo, the Bucks could have boasted the league's most dominant frontcourt.

Minnesota Timberwolves: Not Drafting Stephen Curry, Twice

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    The 2009 NBA draft will forever haunt the Minnesota Timberwolves.

    The Timberwolves owned the Nos. 5 and 6 overall picks in the draft, and Blake Griffin, Hasheem Thabeet, James Harden and Tyreke Evans came off the board with the first four picks, respectively.

    Minnesota needed guard help, which made Stephen Curry the seemingly obvious choice. After putting himself and Davidson on the national radar during the 2008 NCAA tournament, he averaged 28.6 points per game the following season as a junior.

    The Wolves did take a guard, but they passed on Curry to select Ricky Rubio and Jonny Flynn instead. 

    Although Rubio has gone on to have a successful NBA career, Flynn was out of the league after only three seasons. Meanwhile, Curry has won two MVPs, three NBA titles and revolutionized the league with his three-point shooting ability.

    Minnesota missed out on pairing him with Kevin Love, which would have laid the blueprint for one of the best outside-shooting teams in the league.

New Orleans Pelicans: Trading for DeMarcus Cousins

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    Pairing two dominant big men was a great idea in the NBA...25 years ago.

    In today's era of pace and space, it's better to surround an All-Star power forward or center with perimeter threats, not load up on another All-Star big with an overlapping skill set.

    That's precisely what the New Orleans Pelicans did when they traded for DeMarcus Cousins to pair with Anthony Davis.

    While Cousins put up monster numbers with the Pelicans (25.0 points, 12.7 rebounds and 5.0 assists in 65 games), the team missed the playoffs in 2016-17, and Cousins missed the 2017-18 postseason with a torn Achilles tendon.

    Without Cousins, the Pelicans still swept the Portland Trail Blazers in the first round of the playoffs before losing to the eventual champion Golden State Warriors.

    Had New Orleans not made the trade, a backcourt of Jrue Holiday and Buddy Hield would have been an outstanding fit next to Davis. The Pelicans then would have had their choice of Donovan Mitchell, Bam Adebayo, John Collins, Jarrett Allen or OG Anunoby with the No. 10 overall pick in 2017.

New York Knicks: The Isiah Thomas Years

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    At this point, it might be easier to make a list of the things the Knicks have done right over the last 20 years.

    While they've had plenty of coaching changes, failed draft picks and awful contracts, the Isiah Thomas era in New York may be the worst in the past few decades.

    Thomas served in a plethora of roles including team president, general manager and eventually head coach. His time in New York included bringing in past-their-prime guards on bloated contracts and providing other teams with valuable cap space.

    At one point, Thomas compiled a backcourt of Stephon Marbury, Steve Francis, Nate Robinson and Jamal Crawford, four ball-dominant guards who were far more interested in getting their own shots up rather than setting up teammates.

    Thomas handed head coach Larry Brown a five-year, $50 million contract in 2005 and then fired him after only one season. Brown and the Knicks would eventually settle on a $18.5 million payout, meaning Thomas paid him $28.5 million for 23 total wins.

    Thomas' solution was to then make himself the head coach, but the Knicks went 33-49 in 2006-07 and 23-59 in 2007-08.

    The Knicks finally relieved Thomas of all of his duties following the 2007-08 season, although they reportedly considered him for the team president position again nine years later.

Oklahoma City Thunder: Not Offering James Harden an Extra $5 Million

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    Despite losing the 2012 NBA Finals, the Oklahoma City Thunder looked like a blossoming dynasty with Kevin Durant, Russell Westbrook and James Harden. All were in their early 20s and were already some of the most talented scorers in the league at their respective positions.

    But when it came time to pay Harden, the Thunder got cheap. OKC offered Harden a four-year extension worth around $55 million extension, according to ESPN's Brian Windhorst, which was $5 million short of a max deal.

    The Thunder warned Harden that they would trade him if he didn't agree to the extension they offered. They eventually dealt him to the Houston Rockets for Jeremy Lamb, Kevin Martin, first-round picks in 2013 and 2014 and a second-round pick in 2013.

    While the Thunder used that 2013 first-rounder to select Steven Adams, this was still a horrible trade. It elevated Houston into a playoff regular and weakened the Thunder, who never reached the NBA Finals again following his departure.

    Had the Thunder offered Harden just $1.25 million more per year, there's no telling how successful they would have become.

Orlando Magic: Trading for Serge Ibaka and Trading Away Serge Ibaka

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    It's easy to forget Serge Ibaka's tenure with the Orlando Magic, which lasted only 56 total games.

    The Oklahoma City Thunder traded Ibaka to the Magic in 2016 in a deal that landed them 2013 No. 2 overall pick Victor Oladipo, Domantas Sabonis and Ersan Ilyasova. It was a tremendous deal for OKC, who would later send Oladipo and Sabonis to the Indiana Pacers for Paul George.

    Giving up on Oladipo that early seemed like a mistake for Orlando, as he was developing into a two-way force who provided a good balance with Nikola Vucevic and Aaron Gordon. The Magic weren't a playoff team, so getting a veteran like Ibaka was pointless.

    With Ibaka in the final year of his contract and Orlando not in playoff contention, the Magic flipped him to the Toronto Raptors halfway through the 2016-17 season for Terrence Ross and a first-round pick.

    It's hard to explain why the Magic traded for Ibaka in the first place. It looks far worse now that Oladipo and Sabonis both turned into All-Stars after leaving Orlando.

Philadelphia 76ers: Trading Up for Markelle Fultz

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    The Philadelphia 76ers' Process was by no means seamless.

    While losing season after losing season resulted in some high draft picks, those picks weren't guaranteed to hit. Taking Jahlil Okafor with the third overall pick in 2015 stings, especially with players like Kristaps Porzingis and Devin Booker still available at that point.

    But no player has caused as much frustration and disappointment among Philly fans as Markelle Fultz.

    The 76ers had to trade the No. 3 overall pick in 2017 along with a 2019 first-rounder to move up to No. 1 and select Fultz, a move that now hurts on a number of levels.

    Fultz averaged only 7.7 points, 3.4 rebounds and 3.4 assists over two injury-plagued years before the Sixers traded him to the Orlando Magic for Jonathon Simmons, a top-20 protected 2020 first-round pick and a 2019 second-round pick. Fultz is now averaging 12.1 points and 5.2 assists as Orlando's starting point guard.

    Staying put at No. 3 would have allowed the Sixers to draft Jayson Tatum, who's now an All-Star with the Boston Celtics. Tatum, Joel Embiid and Ben Simmons would have made for one of the NBA's best young Big Threes, and Philly would have gotten to keep its 2019 first-round pick.

Phoenix Suns: Not Taking Luka Doncic No. 1

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    Deandre Ayton is averaging 17.1 points on 57.2 percent shooting, 10.8 rebounds, 1.2 blocks in his first two NBA seasons. While those are impressive numbers, the Phoenix Suns should still regret taking him over Luka Doncic with the No. 1 overall pick in 2018.

    Doncic has not only established himself as the best player in the draft class, but he's already knocking on the door of being one of the league's top overall stars.

    A backcourt of Doncic and Devin Booker would have devastating for opponents, as the two are combining for 54.8 points per game this season with the Dallas Mavericks and Suns, respectively.

    Doncic already has the Mavericks in line for a playoff spot this season, while Ayton, Booker and the Suns are likely headed for a 10th straight trip to the lottery.

    The best the Suns can hope for is a 1984 draft situation, where the Houston Rockets took Hakeem Olajuwon with the No. 1 overall pick while Michael Jordan slipped to the Chicago Bulls at No. 3.

    As good as Ayton is and will be, Doncic will always be better.

Portland Trail Blazers: Picking Greg Oden over Kevin Durant

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    The No. 1 overall pick in 2007 came down to Ohio State center Greg Oden and Texas forward Kevin Durant, both of whom had just dominated the college basketball season.

    Oden was a 7'0" two-way force who could dominate the paint on both ends. Durant was an elite scorer, using his 7'5" wingspan to shoot over opponents with ease.

    The Portland Trail Blazers even put up billboards asking fans to honk for whichever player they wanted the team to draft.

    Oden won out at the end, although knee surgery caused him to miss his entire rookie season. Meanwhile, Durant averaged 20.3 points per game with the Seattle SuperSonics.

    Oden played only 82 total games in Portland because of injuries, although he was productive when he was healthy enough to suit up (9.4 points, 7.3 rebounds and 1.4 blocks in 22.1 minutes).

    However, Durant became one of the NBA's best players, an MVP who's led the league in scoring four times.

Sacramento Kings: Almost Every Draft Pick Since 2000

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    Not much has gone right for the Sacramento Kings in the past two decades. 

    The primary reason? The draft.

    While DeMarcus Cousins, De'Aaron Fox, Kevin Martin and Tyreke Evans were quality picks, the rest of Sacramento's draft history this millennium is brutal.

    The Kings picked in the top eight for four straight years from 2012 to 2015, only to come away with Thomas Robinson, Ben McLemore, Nik Stauskas and Willie Cauley-Stein. Not only are all four no longer in Sacramento, but Robinson and Stauskas are out of the NBA entirely.

    The jury is still out on 2018 No. 2 overall pick Marvin Bagley III, as injuries have limited him to only 75 games over two seasons so far. When he does return to the court, he'll have a lot of ground to make up to catch Luka Doncic, the player who went directly after him in the 2018 draft.

San Antonio Spurs: Trading Kawhi Leonard

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    The Spurs haven't made many mistakes since the mid-1990s, but trading Kawhi Leonard to the Toronto Raptors was a rare exception.

    Moving Leonard was bad enough, but including starting shooting guard Danny Green in the deal seemed excessive. While DeMar DeRozan was fresh off three straight All-Star nods, the combination of him, Jakob Poeltl and a 2019 first-round pick for both Leonard and Green didn't come close to being equal value.

    During his lone season in Toronto, Leonard led the Raptors to their first-ever championship and captured Finals MVP honors. Even though he and Green both departed in free agency last summer, the Raptors should have no regrets about what they gave up to win a ring.

    DeRozan has continued to put up numbers in San Antonio, albeit on a Spurs team that looks destined to miss the playoffs for the first time this century. He's also reportedly "not happy" in San Antonio, according to CNBC's Jabari Young, and could become an unrestricted free agent this offseason by declining his $27.7 million player option for the 2020-21 season.

    The Spurs needed to get a superstar back from Leonard, or at least some significant young talent and draft picks to kick off what's looking like an inevitable rebuild. They failed at both.

Toronto Raptors: Trading Vince Carter

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    Before DeMar DeRozan, Kyle Lowry and even Kawhi Leonard, Vince Carter was the Toronto Raptors.

    The high-flying shooting guard averaged 23.4 points per game in six-and-a-half seasons with the Raptors, quickly becoming the best and most popular player in the franchise's short history.

    With Carter's production dropping and the Raptors struggling in 2004-05, Toronto made the difficult decision to trade him to the New Jersey Nets. He went on to average 23.6 points in four-and-a-half years with the Nets.

    The Raptors needed a monster haul to justify trading Carter, but they instead received Alonzo Mourning (who never reported to them), Aaron Williams, Eric Williams and first-round picks in 2005 and 2006 that became Joey Graham and Renaldo Balkman, respectively.

    Carter and second-year forward Chris Bosh could have formed a tremendous one-two punch. If nothing else, Toronto should have gotten a better collection of talent back for Carter to place around Bosh.

Utah Jazz: Not Giving Gordon Hayward a 5-Year Deal in 2014

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    Instead of signing Gordon Hayward to an extension in 2013, the Utah Jazz allowed him to become a restricted free agent the following summer.

    That decision wound up backfiring on them.

    While the Jazz liked Hayward, they weren't willing to give him a full five-year, $80 million max deal. Instead, they let him sign an offer sheet elsewhere, which they would have the right to match.

    Hayward ended up signing a four-year, $63 million offer sheet with the Charlotte Hornets, which the Jazz agreed to match. While that kept Hayward in Utah for three more seasons, the fourth year of the contract was a player option that he decided to decline.

    Had the Jazz signed Hayward to a five-year max extension when they had the chance, Hayward wouldn't have become a free agent until after the 2018-19 season. Instead, he left to sign with the Boston Celtics in the summer of 2017.

    The trio of Hayward, Donovan Mitchell and Rudy Gobert would have been a tremendous core to build around had Utah given Hayward a five-year deal instead of allowing him to test restricted free agency.

Washington Wizards: Giving Gilbert Arenas $111 Million

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    The Washington Wizards' decision to sign Gilbert Arenas to a six-year, $111 million contract was bad enough, but it could have been even worse.

    According to the Associated Press, the Wizards originally offered Arenas a six-year, $127 million max deal, but he decided to take less so the team had more money for Antawn Jamison.

    While Arenas was one of the NBA's top players when he signed his mammoth deal in July 2008, his body soon betrayed him. Knee injuries and a suspension for bringing a gun into the Wizards’ locker room limited Arenas to only 121 total games over the next four years.

    Arenas bounced around from the Wizards to the Orlando Magic and Memphis Grizzlies while still trying to earn his massive contract. He averaged only 13.0 points on 38.6 percent shooting overall over those four seasons, easily becoming the worst contract in the NBA at the time.

    The Wizards can only hope John Wall doesn't follow in Arenas' footsteps.