2. Gordon Hayward
The signing of Gordon Hayward is arguably one of the biggest signings in Celtics history. Hayward was coming off an All-Star season with the Jazz averaging 21.9 points, 5.4 rebounds, and 3.5 assists per game. Boston managed to lure Hayward away to reunite with his former college coach, Brad Stevens, signing the forward to a four-year, $128 million deal.
In his very first regular-season game wearing Celtics green, Hayward suffered one of the most gruesome injuries in sports following a failed alley-oop attempt. It would take him over a year to recover from his injury before returning to the team. When the Butler product managed to return to the lineup, he understandably struggled to return to his former self. Hayward averaged 13.4 points, 5.4 rebounds, and 3.6 assists in 125 games during his time with the Celtics.
Following the Celtics’ loss to the Miami Heat in the Eastern Conference Finals in 2020, Hayward decided it was time for a change of scenery. Despite the injury, Hayward managed to sign yet another max deal just years later. The dynamic player landed a four-year, $120 million deal with the Charlotte Hornets.