10 most gutsy NBA trade deadline deals that didn't pay off

03/31/2025 03:30 PM

The trade deadline is a golden opportunity for all NBA teams to make some roster improvements. In fact, earlier this year we saw a chaotic deadline that saw various contenders make blockbuster moves for a superstar. While those deals are usually risky, they don’t always pay off in the end. Here is a look at the 10 most gutsy trade deadline deals that didn’t pay off.

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Suns trade for Kevin Durant (2023)

The Phoenix Suns were the center of the attention at the NBA’s trade deadline in 2023 when they managed to acquire Kevin Durant from the Brooklyn Nets. In order to get Durant, the Suns gave up a huge chunk of their draft capital filled with first-round draft picks coupled with important young core pieces in Cameron Johnson and Mikal Bridges.

However, surrendering their future has finally caught up as even with a big three of Durant, Devin Booker, and Bradley Beal, the team doesn’t have a clear path to a championship let alone making the postseason this year.

Knicks land Carmelo Anthony (2011)

The New York Knicks came away from the 2010 free agency a little bit disappointed, as they failed to lure LeBron James. While they did manage to land Amar’e Stoudemire, Knicks fans felt they could use a little more star power. With Carmelo Anthony disgruntled with the Denver Nuggets, the team didn’t wait until his contract expired at the end of the season. Instead, the Nuggets, Knicks, and the Minnesota Timberwolves engaged in a three-team trade that landed Melo in New York.

Landing the 10-time NBA All-Star was supposed to power the Knicks back to relevancy. However, Melo was too selfish to be a championship player. Although he electrified Madison Square Garden with his individual performances, the team was nowhere near a playoff threat. Furthermore, the Knicks basically gutted their roster just to get him.

The Ray Allen-Gary Payton swap (2003)

Trades are often one-sided. However, there are times when a trade doesn’t benefit both parties at all. The Seattle Supersonics wanted to get younger, so they traded their face of the franchise in Gary Payton for a 26-year-old sharpshooting Ray Allen. Allen transformed into a star. However, he wasn’t the player who would bring a title to Seattle. On the other hand, the Bucks had problems of their own with Payton and coach George Karl’s relationship.

Sixers swap disgruntled stars with the Nets (2022)

The Philadelphia 76ers and Brooklyn Nets had one common issue during the 2021-22 season. They both dealt with disgruntled superstars. As a result, it only made sense that both teams engaged in a blockbuster deal at the trade deadline.

The Nets traded James Harden and Paul Millsap for the Sixers’ Ben Simmons, Andre Drummond, Seth Curry, and a pair of first-round draft picks. Harden failed to mesh well with 2023 NBA MVP Joel Embiid in Philly while Simmons continued to stay out of action for the most part of his tenure in Brooklyn.

Nets pry away Deron Williams from the Jazz (2011)

Deron Williams established himself as a star in Salt Lake City. However, a long-awaited fallout with Jerry Sloan finally happened, leading the Utah Jazz to send him to the Brooklyn Nets. The Jazz got Derrick Favors, Devin Harris, and a pair of first-round draft picks in return. The Nets finally landed their first superstar since relocating to Brooklyn. However, Williams’ stints with the Nets was marred with injuries and early playoff exits.

Heat gamble on Victor Oladipo (2021)

Fresh from an appearance at the 2020 NBA Finals, the Miami Heat knew they needed to bolster their roster to make a return trip. As a result, at the trade deadline, the Heat swung for two-time NBA All-Star Victor Oladipo, who was supposed to add more shot creation to the team.

In exchange, they gave up depth and veteran presence, surrendering Kelly Olynyk and Avery Bradley to go along with a first-round draft pick. Shortly after, Oladipo suffered a season-ending surgery. The former NBA Most Improved Player never really found his groove in Miami.

Pacers land Evan Turner (2014)

The Indiana Pacers were no doubt dark horses of the Eastern Conference, especially with Paul George at the helm. At the trade deadline, they intended to fortify their playoff hopes by trading their former face in Danny Granger in exchange for Evan Turner and Lavoy Allen. Unfortunately, the move backfired as it hampered the team’s already established chemistry. Furthermore, it also didn’t help that Lance Stephenson and Evan Turner hardly got along in Indiana.

Cavaliers land aging defensive star Ben Wallace (2008)

After suffering a sweep at the hands of the San Antonio Spurs at the 2007 NBA Finals, the team knew they needed more star power to supplant LeBron James. As a result, they decided to pursue a familiar former Pistons rival in Ben Wallace. Unfortunately, Wallace was already way past his best years.

Nonetheless, the Cavs still pulled the trigger by shipping out Drew Gooden, Larry Hughes, Shannon Brown, Cedric Simmons, Donyell Marshall and Ira Newble. Despite sacrificing a lot, the Cavs never returned to the Finals stage before James took his talents to South Beach.

Lakers move on from Russell Westbrook by reuniting with D’Angelo Russell (2023)

The Russell Westbrook experiment with the Lakers was easily a failure. As a result, the Purple and Gold tried to salvage their season by trading the 2017 NBA MVP All-Star Russell Westbrook for onetime All-Star guard D’Angelo Russell along with some key rotational pieces like Jarred Vanderbilt.

On the bright side, the move did propel the Lakers to a Western Conference Finals appearance despite a disastrous start to the season. However, Russell’s playoff woes prevented the Purple and Gold from kicking it to a higher gear. Moreover, the Denver Nuggets often exploited their weaknesses.

Thunder makes last-minute veteran addition in Gordon Hayward (2024)

The Oklahoma City Thunder could’ve used a veteran for their playoff push. As a result GM Sam Presti capitalized at the trade deadline by making a move for former NBA All-Star Gordon Hayward. To get him, the Thunder didn’t exactly give up significant pieces, but it was relatively a lot for a star on his last legs. Oklahoma gave up Vasilije Micic, Tre Mann, Davis Bertans, and two second-round picks. Hayward failed to buy in to the Thunder’s system, forcing Presti to regret the move. 

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