The Worst Lose-Lose Trades in Modern NBA History

Greg Swartz@@CavsGregBRCleveland Cavaliers Lead WriterJune 14, 2020

The Worst Lose-Lose Trades in Modern NBA History

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    While there's typically a clear winner in most NBA trades, this isn't always the case.

    Ideally, both teams come away feeling like they won the deal, especially after enough time has passed. While there's been plenty of instances of win-win trades over the past few decades, the opposite has also proved true.

    These are some of the worst deals that have gone down over the past four decades for all teams involved.


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    The Trade: Los Angeles Clippers traded Bill Walton to Boston Celtics for Cedric Maxwell and 1986 first-round pick on Sept. 6, 1985.

    Walton's trade from the Clippers to the Celtics in 1985 was far from glamorous, although the story of how it went down remains one for the ages.

    Walton was nearly 33 and had already missed three full seasons with foot injuries, as his body was breaking down following All-Star campaigns with the Portland Trail Blazers. With the Clippers, Walton was still productive (11.9 points, 9.0 rebounds, 2.3 blocks per game) when he could get on the court.

    The future Hall of Famer wanted to play for Boston so badly he called Celtics president Red Auerbach and convinced him to negotiate with Clippers owner Donald Sterling.

    Even though the deal eventually went through, Walton had to pass a physical after piling up years of injuries. As the big man told Adrian Wojnarowski, then of Yahoo, this was no guarantee (h/t Henry McKenna of

    "And then I got to the Boston Celtics, and the biggest problem was that I still had to pass a physical because there's no way I'd ever been able to pass a physical. But Red Auerbach, he showed up at the hospital. And the doctors are all looking at my X-rays. And I could hear them talking. And I had just left everything back in California, and I'm coming here, moving to Boston, with no idea how it was all going to play out. And so I could hear the doctors talking among themselves: 'What are we going to tell Red? We can't pass this guy. Look at his feet. Look at his knees. Look at his hands and wrists. Look at his spine. Look at his face. There's no way we can pass this guy.'"

    Auerbach ignored the team doctors and approved the deal anyway.

    Walton would go on to play in just 90 regular-season games over the next three years, averaging 7.0 points and 6.4 rebounds. Although he filled a backup center role on the 1985-86 Celtics championship team, Walton was far from his prime and would retire after playing his last game in 1987.

    For the Clippers, Maxwell, the 1981 Finals MVP, lasted just a year-and-a-half before being traded to the Houston Rockets in 1987 for draft picks.

    The pick that Los Angeles got for Walton eventually turned into Arvydas Sabonis, which would have made the Clippers winners in this deal had the team not traded it just four months later.


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    The Trade: Atlanta Hawks traded Dominique Wilkins and 1994 first-round pick to Los Angeles Clippers for Danny Manning on Feb. 24, 1994.

    After spending nearly 12 seasons in Atlanta and becoming a superstar with the Hawks, Wilkins was still playing at a high level when he was traded to the Clippers in 1994.

    In his age-34 campaign, Wilkins was averaging 24.4 points per game for a Hawks team that was 36-16 and was looking to make major noise in the playoffs after Michael Jordan switched to professional baseball.

    Instead, Atlanta traded Wilkins and a first-round pick to the Clippers for Manning, a power forward who was six years younger but about to hit free agency.

    It was a terrible trade all around, as the Hawks lost the best player in franchise history, gave up a first-round pick and saw Manning leave for the Phoenix Suns as a free agent. Before he did, Atlanta fell to Reggie Miller's Pacers in the second round.

    The Clippers couldn't convince Wilkins to stay either, as he played just 25 games in L.A. before signing with the Boston Celtics.


    The Trade: Chicago Bulls traded Scottie Pippen to Houston Rockets for Roy Rogers and 2000 second-round pick on Jan. 22, 1999.

    While Pippen was heading out the door after Jordan's second retirement in 1998, this was still a bad trade for both the Bulls and Rockets.

    Pippen had played well in a leading role during Jordan's first retirement in 1993, finishing third in MVP voting while leading Chicago to the playoffs. Building around him in 1998 at age 33 may not have been the right choice, but not even trying to work things out (even with the intention of finding a trade partner later) seemed like a wasted opportunity for the second-best player in franchise history.

    Chicago waived Rogers almost immediately. Jake Voskuhl was taken using the second-round pick but would only play 16 games as a rookie before the rebuilding Bulls traded him to the Phoenix Suns a year later. The Bulls should have at least leveraged Pippen's sign-and-trade into better draft picks, a la what the Cavaliers and Raptors did with the Miami Heat in 2010 for LeBron James and Chris Bosh, respectively.

    Pippen would only play one year in Houston before being traded to the Portland Trail Blazers, failing to get along with Charles Barkley, as both stars were past their primes. The former would later say that Barkley owed him an apology for coming to play with his "sorry fat butt," and that he wouldn't even apologize to Barkley if held at gunpoint.

    Overall, neither team won this deal.


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    The Trade: Sacramento Kings traded Chris Webber, Matt Barnes and Michael Bradley to Philadelphia 76ers for Kenny Thomas, Brian Skinner and Corliss Williamson on Feb. 23, 2005.

    Webber was the best player on some really good Kings teams in the early 2000s and was still averaging 21.3 points, 9.7 rebounds and 5.5 assists per game when Sacramento traded him to Philly in 2005.

    The goal for the Sixers was to pair Webber with Allen Iverson to make another run at the Finals.

    While the attempt was noble, Webber just wasn't the same in a sidekick role. His production fell across the board, with his shooting percentage dropping to 42.1 percent in 114 games in Philly. The Sixers won just a single playoff game over parts of three seasons with Webber, eventually agreeing to a buyout with the five-time All-Star in January 2007 after foot and ankle injuries piled up.

    It was the beginning of the end for the Kings as well, as they only received a trio of role players in return. Since the trade 15 years ago, Sacramento has made just two trip to the playoffs, including zero in the past 13 seasons.


    The Trade: Miami Heat traded Shaquille O'Neal to Phoenix Suns for Shawn Marion and Marcus Banks on Feb. 6, 2008.

    While Miami pulled off a brilliant move by bringing in O'Neal from the Los Angeles Lakers in 2004, trading him to the Suns in 2008 helped no one.

    Phoenix had built a run-and-gun offense led by Steve Nash and needed players with speed and athleticism. Instead, the Suns traded for a 35-year-old O'Neal who weighed in excess of 320 pounds.

    Suns general manager Steve Kerr later admitted his mistake to The Ringer's Bill Simmons:

    "I was a young GM. It's the kind of move that, yeah, you go for it, but you're compromising the long-term health of the franchise. That was a mistake. The reasons for making it were not sound. We knew we weren't good enough to win the whole thing. We'd been in it for several years. Kept losing to the Spurs. But it was a rushed, sort of home run swing that we struck out with. We went for it, which is admirable, but I just think we compromised our identity."

    Getting Marion, a 29-year-old four-time All-Star, seemed like a win for Miami, but the Heat traded him just 58 games later to the Toronto Raptors in a deal for an aging Jermaine O'Neal.


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    The Trade: Phoenix Suns traded Steve Nash to Los Angeles Lakers for 2013, 2015 (later conveyed in 2018) first-round picks and 2013, 2014 second-round picks on July 11, 2012.

    No one could blame the Lakers for trading for Nash.

    Even at age 38, he had averaged a double-double of 12.5 points and 10.7 assists per game with the Phoenix Suns the season before. Since the Lakers didn't possess the cap space to sign Nash outright, they agreed to a sign-and-trade in which the two-time MVP received a three-year, $28 million contract.

    Trading for Dwight Howard a month later, the Lakers looked like title contenders with Kobe Bryant, Nash, Pau Gasol and Howard.

    The result was a first-round exit in 2013 and a 15-game season from Nash in 2013-14 before injuries forced him to retire.

    Even with four draft picks to show for Nash, the Suns ended up with nothing of significance in their rebuild. Eight years after trading the Hall of Fame point guard, the Suns have yet to reach the postseason.


    The Trade: Cleveland Cavaliers traded Kyrie Irving to Boston Celtics for Isaiah Thomas, Jae Crowder, Ante Zizic, 2018 first-round pick, 2020 second-round pick on Aug. 30, 2017.

    Getting Irving for a hobbled Thomas seemed like a great deal for the Celtics at the time, especially since the severity of their 5'9" point guard's hip injury was unclear. Boston had stockpiled draft picks from the Brooklyn Nets and Memphis Grizzlies from previous trades, so even giving up an unprotected first from the Nets seemed worth it.

    What transpired was two years of injuries and poor leadership from Irving, who missed the entire 2018 playoff run before leaving as a free agent in 2019.

    The Thomas experiment couldn't have gone any worse for Cleveland, as even his return in January didn't last long. Given that his hip was never surgically repaired, Thomas was a disaster on defense and posted a 36.1 percent shooting percentage when asked to score. He lasted just 15 games before the Cavs traded him to the Los Angeles Lakers in a cap-clearing move for L.A., which sent Jordan Clarkson and Larry Nance Jr. the other way.

    Crowder was traded to the Utah Jazz after 53 games, and Zizic has battled injuries and been buried on Cleveland's bench for three years.

    While the Cavs at least got Collin Sexton via the Nets' first-round pick, they still lost one of the best players in franchise history in Irving, helping to open the door for LeBron to also leave in 2018.


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