1. Dwight Howard
In the summer of 2016, five-time First Team All-NBA big man Dwight Howard declined his player option with the Houston Rockets and chose to instead join his hometown team in Atlanta. The Hawks signed Howard on a three-year, $70 million contract entering the 2016-17 NBA season.
The signing was considered to be good but not earth-shattering. Dwight’s best years with the Orlando Magic were behind him. He was still a decent starting center, but not quite the game-changer he used to be. In his one season with Atlanta, Howard averaged a solid 13.5 points and 12.7 rebounds on 63% shooting.
But at the end of the first year of his contract, the Hawks opted to trade Dwight to Charlotte for Miles Plumlee, Marco Belinelli, and a second-round pick. Considering both those players were out of the league three years later, it is not a trade that reflects positively on the Hawks. But the real kicker was what Howard accomplished after leaving Atlanta.
Dwight never returned to All-Star form, but he showed he was still a championship-level role player in helping the Lakers win the 2020 NBA Championship in the Orlando bubble. He averaged career-high field goal percentages in both the regular season and postseason for Los Angeles.
Seeing how Howard continued to flourish and extend his career after leaving the ATL has to be sickening for Hawks fans. Letting the hometown hero go for the price they did is one move the organization definitely wishes it could do over.