Ranking the best trades the Boston Celtics ‘almost’ made under Danny Ainge

3. Kawhi Leonard

When the San Antonio Spurs began shopping Kawhi Leonard during the 2018 offseason, the Celtics appeared ready to pounce.

They were “among [the] teams” who made offers to the Spurs for him, according to ESPN, and Wojnarowski noted “Boston has long had the assets that the Spurs most covet in a potential Leonard trade.” However, he added that the Celtics were being “extremely cautious on [the] Leonard front” because of the uncertainty with his future, and they had “no intention” of making a risky trade.

In early July, Wojnarowski said the Celtics had made their “top five players off-limits” and preferred to “do a deal that’s pick-heavy,” but the Spurs wanted “good players back.” The Toronto Raptors eventually swooped in and sent DeMar DeRozan, Jakob Poeltl and a first-round pick to the Spurs for Leonard and Danny Green.

The Raptors went on to win that year’s NBA title, while some people within the Celtics organization ended up feeling regret about “not pulling the trigger” on a Leonard trade, according to Chris Mannix of Sports Illustrated.

“Assuming what we know (about their pursuit) is true, it was questionable at the time,” one rival executive told The Athletic’s Jay King about the Celtics’ failure to land Leonard. “Now, it looks worse.”