The Danny Ainge era in Boston came to an inglorious end Wednesday when the team announced, a day after it was bounced from the playoffs, that he was stepping down. Brad Stevens, the Celtics coach for the past eight seasons, is leaving the sidelines to replace Ainge as president of basketball operations.

Celtics fans might feel a certain way about how things have unfolded in the franchise’s front office recently—the Kyrie Irving jokes are flying around and that situation certainly represented a low point. But Ainge’s legacy as an executive—after a successful stint as a player in Boston from 1981-89 where he won two titles and earned his only All-Star nod—was filled with more successes than failures. Most notably, he gets credit for building the 2007-08 team that won the organization’s first NBA title in 22 years. 

Even if the Celtics were a mess this past season, grossly underachieving for a variety of reasons, Ainge leaves his post after 18 seasons with a reputation as one of the most respected roster builders and decisions makers in the NBA.

While Ainge will forever be lauded for acquiring Kevin Garnett and Ray Allen to complement Paul Pierce on that title team and fleecing Brooklyn in the deal that sent an aging KG and Pierce to the Nets for picks that eventually netted them their current cornerstones (Jayson Tatum and Jaylen Brown), he did not always land the players he coveted. 

Every team has plenty of woculdas, couldas, shouldas and Ainge, with all his wheelings and dealings over the nearly two decades he ran the Celtics, whiffed on a number of top players. On his way out of Boston here are Ainge’s most notable trades he couldn’t consummate.