Ranking the Worst NBA Midseason Trades Since 2000

David KenyonFeatured ColumnistFebruary 26, 2021

Ranking the Worst NBA Midseason Trades Since 2000

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    One horrible midseason trade helped the Cavaliers land Kyrie Irving.
    One horrible midseason trade helped the Cavaliers land Kyrie Irving.Bill Kostroun/Associated Press

    Every NBA trade has good intentions. If bolstering the roster means giving up a promising young player or a draft pick, that's simply the cost of doing business.

    Hindsight is often unkind, however.

    In the last 20 years, NBA teams have engineered some disastrous trades after a season began. Whether it was merely a few days into the campaign, like the Allen Iverson/Chauncey Billups swap in 2008, or around the February deadline, these agreements didn't pan out as hoped.

    The order is subjective but considers future production of the players and draft picks involved, as well as team performance.

8. Suns Trade Isaiah Thomas to Celtics

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    Brandon Dill/Associated Press

    In the 2014-15 season, the Phoenix Suns had a perimeter logjam. They carved out minutes for Eric Bledsoe, Goran Dragic and Isaiah Thomas but decided to make a change at the Feb. 19 trade deadline.

    That marked a horrible day in franchise history.

    Phoenix sent Dragic to the Miami Heat after he demanded a trade. In exchange, the Suns got two first-rounders that they used to acquire Mikal Bridges from the Philadelphia 76ers shortly after he was drafted in 2018. Bridges' strong start to the 2020-21 season may still redeem that particular deal. Acquiring Brandon Knight from the Milwaukee Bucks didn't help or hurt anyone, really. But moving Isaiah Thomas to the Boston Celtics for Marcus Thornton and a first-round pick proved costly.

    Thomas developed into an All-Star in Boston, while Thornton managed just nine appearances with the Suns. Phoenix later packaged the first-rounder with Bogdan Bogdanovic in a trade to the Sacramento Kings that landed Marquese Chriss.

    Within a year, then-general manager Ryan McDonough admitted it was a mistake. It can't be pinned entirely on the Thomas trade, but Phoenix didn't win 30 games again until the 2019-20 season.

7. Bucks Send Ray Allen to Seattle

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    LUCY NICHOLSON/Associated Press

    As tension grew between Ray Allen and head coach George Karl, the Milwaukee Bucks had a decision to make. Keep the player, or keep the coach? They chose...poorly.

    "That was our most unfortunate moment, letting Ray Allen leave town," former team owner Herb Kohl later said.

    Milwaukee sent Allen, Ronald Murray, Kevin Ollie and a first-round pick (Luke Ridnour) to Seattle for Gary Payton and Desmond Mason. Payton appeared in 28 games but immediately bolted as a free agent, and Mason—well, he wasn't Ray Allen.

    The sharpshooter averaged 24.6 points in four-plus seasons with the SuperSonics and eventually broke the NBA record for career three-pointers made.

6. Carmelo Forces His Way to New York

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    Darron Cummings/Associated Press

    After adding Amar'e Stoudemire in July 2010, the New York Knicks took aim at a title. Midway through 2010-11, they traded for Carmelo Anthony, who had made it clear he wouldn't re-sign with the Denver Nuggets. The diverging paths resulted in a mammoth three-team deal involving the Minnesota Timberwolves.

    In short, Carmelo went to Denver, and the Nuggets returned a haul of young players and picks.

    In short-short: Nobody won the trade.

    Carmelo stayed for six-plus seasons, but New York won a single first-round series in three playoff trips. Denver had a great run in 2012-13 before Danilo Gallinari's ACL tear, which ultimately sparked a rebuild. Minnesota never threatened for a playoff bid.

5. Pistons Collapse After Iverson, Billups Swap

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    David Zalubowski/Associated Press

    During the 2000s, few Eastern Conference teams enjoyed more success than the Detroit Pistons. They appeared in six Eastern Conference Finals, won two and celebrated one NBA title.

    But the seven-year streak of 50-plus victories ended when the Pistons sent Billups to Denver in 2008.

    In order to acquire Allen Iverson, Detroit parted with Billups and Antonio McDyess. Iverson had a Hall of Fame career, but he experienced a massive drop in production that season. Billups, meanwhile, thrived in Denver and helped the Nuggets to the Western Conference Finals for the first time in 24 years.

    Detroit edged into the playoffs at 39-43, exited in a first-round sweep and failed to crack 32 wins in the next six seasons.

4. Boston Deals a Young Joe Johnson

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    DAVID J. PHILLIP/Associated Press

    "Championship contention" is a dangerous thing. Winning a title is the ultimate goal, but the short-term gain can result in a long-term sacrifice. And the Celtics know it awfully well.

    At the 2002 trade deadline, Boston believed it could make a deep playoff run. The team traded rookie Joe Johnson and a first-round selection to Phoenix for Tony Delk and Rodney Rogers, who joined the rotation but were simply complementary pieces.

    The Celtics fell to the New Jersey Nets in the Eastern Conference Finals, and then Rogers left for New Jersey in free agency that summer. Boston traded Delk to the Dallas Mavericks ahead of the 2003-04 season.

    Johnson, on the other hand, became a versatile offensive weapon in Phoenix and a six-time All-Star with the Atlanta Hawks.

3. Raptors Lose Vince Carter for Little

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    BILL KOSTROUN/Associated Press

    When the relationship between Vince Carter and the Toronto Raptors soured, a trade became inevitable. Even in that situation, though, the franchise losing its superstar wants a decent return.

    Unfortunately for Toronto, that didn't happen here.

    Carter went to the Nets, who sent back Alonzo Mourning, Aaron Williams, Eric Williams and two first-round selections. Mourning refused to report, landing a buyout. Neither of the Williams made a substantive impact, and the Raptors turned the draft capital into four-year reserve Joey Graham and the last eight games of Antonio Davis' NBA career.

    New Jersey managed two postseason series wins in Carter's tenure, so it's important to not overrate the result.

    Still, Carter averaged 23.6 points in his four-plus seasonsand scored more points in 2006-07 than Graham and Davis contributed overall to the Raptors after the trade.

2. Nets Add Gerald Wallace, Gift Damian Lillard to Blazers

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    Jim Mone/Associated Press

    New Jersey clearly won the Carter deal, but the franchise's Brooklyn era started with a couple of complete duds.

    As the Nets prepared for the inaugural Brooklyn season in 2012-13, they attempted to build a contender around Deron Williams. Despite their lottery-bound record, they packaged Mehmet Okur, Shawne Williams and a first-round pick for Portland Trail Blazers wing Gerald Wallace.

    Not only did Wallace have a mediocre stay in Brooklyn, but Portland also selected Damian Lillard in the 2012 draft. He's now a six-time All-Star and five-time All-NBA selection.

    And somehow, it gets worse.

    The ensuing offseason, Brooklyn moved Wallace to the Celtics as part of the infamous Paul Pierce and Kevin Garnett trade. While it resulted in a long rebuild for the Nets, Boston used the draft capital to become an Eastern Conference contender.

1. Clippers Lose out on Kyrie Irving

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    Mark Duncan/Associated Press

    After nearly two decades of losing, the Los Angeles Clippers saw a bright future with Blake Griffin, Eric Gordon, DeAndre Jordan and Eric Bledsoe. They viewed the 2011 deadline as an ideal moment to clean up the books and dump salary.

    If only they had waited six months.

    However, the 21-37 Clips attached a first-round pick to Baron Davis' pricey contract and found a suitor in the Cleveland Cavaliers. Still reeling from LeBron James' departure, Cleveland welcomed the chance to add a near-certain lottery pick for starting guard Mo Williams and backup Jamario Moon.

    Despite finishing with the NBA's eighth-worst record, the Clippers endured the ultimate draft lottery pain: the pingpong balls awarded them the No. 1 slot, but Cleveland now owned the pick.

    The Cavs drafted Kyrie Irving, who merely won 2011-12 Rookie of the Year, made four All-Star teams in Cleveland and buried the winning shot in Game 7 of the 2016 NBA Finals.