Ainge's playing style embodied hustle and heart. Undersized yet relentlessly competitive, he earned the nickname "The Microwave" for his ability to instantly heat up a game with his scoring bursts. While never averaging over 20 points a season, his clutch performances in high-pressure situations were legendary. He famously hit a game-winning three-pointer against the Milwaukee Bucks in the 1984 playoffs, a shot that cemented his place in Celtics lore.

Following his playing career, Ainge's shrewd basketball mind shone through. He transitioned seamlessly into the role of executive, first with the Phoenix Suns and later returning to his beloved Celtics as General Manager in 2003. He quickly gained a reputation for his bold trades and strategic maneuvering. Ainge masterminded the acquisitions of Kevin Garnett and Ray Allen, forming a "Big Three" that brought the 2008 NBA championship back to Boston, ending a 22-year title drought.

Throughout his tenure, Ainge continued to wheel and deal, accumulating draft picks and building a sustainable contender. He drafted future stars like Paul Pierce, Rajon Rondo, and Jayson Tatum, ensuring the Celtics remained competitive for over a decade. Even after stepping down as GM in 2021, Ainge remained with the organization as President of Basketball Operations, guiding the franchise through yet another rebuild.