9. So long, Jimmy Buckets
Upon taking a peek at this trade, it looks horrendous. However, the circumstances surrounding the 2018 trade made it necessary. After a single season in Minnesota, Jimmy Butler wanted out of the Twin Cities.
The former Chicago Bulls' forward came to training camp bothered and lasted only 10 games before departing for Philadelphia. He made it known that he wanted out, eliminating any hope of recouping solid assets from a trade partner. The Wolves dealt the disgruntled All-Star to the 76ers in exchange for Robert Covington, Dario Saric, Jerryd Bayless, and a 2022 second-rounder.
After it was all said and done, the Butler experiment fared horribly in Minnesota. The Wolves received a strong season from the five-time All-NBA wing, but the trade to acquire Butler was extremely detrimental in the long run (more on that later).
Furthermore, Covington, Saric, and Bayless hardly spent any time in Minnesota. Covington played 70 games for the franchise, Saric appeared in 68, and Bayless only suited up for 34. Even though the Wolves' hands were forced, the return was abysmal. Covington and Saric were better players than fits on Minnesota's roster.
Of course, requesting a trade never bodes well for the team of the trade requestee, but there have been far better returns than this one. For instance, after Kyrie Irving requested a trade from the Brooklyn Nets in 2019, they still received an unprotected first-rounder from the Dallas Mavericks.