Ranking The NBA's Biggest Regret Trades Of The 2020s

NBA front offices are judged on what they do. It only takes one trade to turn a franchise around, just like it only takes one wrong move to undo years of planning.

Some blockbuster trades gone wrong in the 2020s have left teams with depleted rosters, lost draft picks or the regret of giving up elite talent.

Here are five of the worst trades in the NBA so far in the 2020s

Luka Dončić traded from the Dallas Mavericks to the Los Angeles Lakers in 2025.

There are few trades in NBA history that have been more maligned than the Mavericks sending Luka Dončić to the Los Angeles Lakers. In return, the Mavericks got Anthony Davis, Max Christie and a 2029 first-round pick.

Dončić was just entering his prime after leading Dallas to the 2024 NBA Finals and Davis was still one of the best defenders in the league even in his 30s.

But it’s so unusual for a franchise player at Dončić’s age and talent to be traded

It’s already being viewed as one of the largest gambles and, possibly one of the biggest mistakes, in the history of the league.

The Phoenix Suns fully commit to Kevin Durant in 2023

The Phoenix Suns’ acquisition of Kevin Durant from the Brooklyn Nets was seen as the final piece in a championship puzzle.

The Suns pulled off a blockbuster trade, shipping Mikal Bridges, Cameron Johnson, four unprotected first-round picks and a first-round pick in 2028.

Durant continued to be an elite player, but the Suns were unable to reach the NBA Finals during his tenure in Phoenix.

Injuries, a shallow roster and a lack of financial flexibility kept the franchise from surrounding him with a sustainable contender.

Jaylen Brown traded from Boston Celtics to Philadelphia 76ers in 2026

Two years later, Jaylen Brown, who was the MVP of the 2024 NBA Finals when he led the Celtics to the championship, was traded to the Philadelphia 76ers in a surprising move.

In return, Boston got two first-round picks, two second-round picks and veteran forward Paul George. Many questioned why the Celtics would trade a 29-year-old All-NBA player in his prime.

George is 36 years old with one of the biggest contracts in the league and a long history of injuries. Brown will now play alongside Joel Embiid and Tyrese Maxey, bolstering one of Boston's most formidable rivals.

Russell Westbrook traded to the L.A. Lakers in 2021

The Lakers traded Kyle Kuzma, Kentavious Caldwell-Pope, Montrezl Harrell and the No. 22 pick in the 2021 NBA Draft to the Washington Wizards for Russell Westbrook, believing they were adding a superstar to extend their championship window.

The Lakers had problems with turnovers, spacing and chemistry. The loss of valuable role players hurt the team’s overall depth, and Westbrook’s ball-dominant style was never the right fit.

Westbrook's first year with the Lakers ended with the team missing the playoffs and the team traded him in 2023, making it one of the franchise's most expensive mistakes.

Damian Lillard traded to the Milwaukee Bucks in 2023

The Bucks traded for Damian Lillard in a three-team trade with the Portland Trail Blazers in one of the biggest trades of the decade. Milwaukee sent away Jrue Holiday, Grayson Allen, Toumani Camara, an unprotected first-rounder and future picks

The deal was set up to give Giannis Antetokounmpo the best chance to win a title, but it didn’t work out.

Injuries and defensive struggles kept Milwaukee from another deep playoff run, and Holiday quickly became a crucial piece of Boston’s 2024 NBA championship.

The NBA has always been a place that rewards boldness, but these trades prove that aggression can be a dangerous game

Those trades will probably become cautionary tales of how one decision can shape the fortunes of a team for years to come