19. Utah Jazz trade Deron Williams to New Jersey Nets
Sorry Nets fans, but you’ve got back to back places on this list… Usually when a star player is traded for prospects, the team giving up the star is the one that ends up regretting it. But with the case of Deron Williams being dealt to the New Jersey Nets from the Utah Jazz, it was actually the Nets that ended up regretting things.
At the trade deadline in 2011, the Nets sent Derrick Favors, Devin Harris, and draft picks that would turn into Enes Kanter and Gorgui Dieng to Utah in exchange for the guard. He quickly dropped from his status as one of the best point guards in the game, and ended up being waived by the Nets in 2015. Hardly the return you’re looking for when you trade your best young players along with multiple first round draft picks.