1. Ditching Garnett still in his prime
Trading your best player in franchise history is never easy. Kevin Garnett's name was synonymous with the Timberwolves throughout the late 1990s and early-to-mid 2000s. Minnesota made a playoff appearance in Garnett's sophomore season and continued the postseason streak for eight consecutive seasons.
Unfortunately for the Wolves, mediocracy began to set in after a Western Conference Finals appearance in 2004. Minnesota retained a similar core in the 2004-05 season, but an aging roster only mustered 44 wins after 58 the year prior.
Minnesota ultimately punted on a 30-year-old Garnett after suffering sub-35-win seasons for consecutive years. The assets the Wolves acquired for the superstar big man were extremely average. Sure, Jefferson impressed in a limited time, but Gerald Green, Theo Ratliff, and Sebastian Telfair were below average (shoutout to Ryan Gomes—he averaged 12.3 points in Minnesota).
In addition to the players Minnesota acquired, they also received two first-rounders. The first-round picks ended up being Johnny Flynn and Wayne Ellington in 2009. Neither Flynn nor Ellington lasted long in Minnesota. Both guards played less than 200 games for the Wolves.
What makes the trade questionable is the lack of draft assets Minnesota acquired for Garnett. For instance, in 2022, the Wolves dealt five first-rounders in exchange for Rudy Gobert. The French big is fantastic and helped Minnesota tremendously, but Garnett is one of the best power forwards of all time and was exchanged for just two draft picks.
The Celtics were right to jump on Garnett and his acquisition led immediately to an NBA Championship. As for Minnesota, the franchise won less than 30 games for five seasons following the Garnett mega-deal. Even though the Hall-of-Famer eventually returned, it would have been nice to see Garnett play his entire career in Minnesota a la Kobe Bryant or Dirk Nowitzki.