Among several teams who had to watch Toronto hoist that Larry O'Brien trophy, the Boston Celtics have to be feeling the most regret. They entered the season with a promising roster mixed with young talent and veteran stars. In the end, it ended up being a bad combination of guys who wanted a little bit more of the spotlight than the Celtics had room for.
They might have been hoisting the trophy themselves though had they made a deal for Kawhi Leonard last summer.
"If there is a team feeling Leonard regret now, it is Boston. The Celtics had the coveted young players and draft picks to outbid Toronto. Boston larded up its offer with draft picks, but declined to include Jayson Tatum or Jaylen Brown without gaining more assurance than was possible about Leonard's health and interest in re-signing, sources said at the time of the trade.
Boston's fretful waffling was understandable in the moment. Brown appeared on track to be an All-Star. Maybe more important, Boston believed it had a championship team already. The Celtics had just taken James and the Cleveland Cavaliers to Game 7 without Kyrie Irving and Gordon Hayward. Was it worth trading a key piece of what appeared then to be both a championship present and future to rent Leonard and watch him leave?
Acquiring Leonard also would have left Boston with four max-salary players in Irving, Hayward, Leonard and Al Horford -- untenable for long. Boston was saving its chips for Anthony Davis. Everyone around the league -- including the Raptors -- wondered if Leonard's health would ever allow him to be the player he was in 2017.
In retrospect, Boston was both too cautious and too optimistic about its existing core.
If you have a chance to win the title and a healthy culture, believe in that culture enough to take a risk that meaningfully boosts those title chances -- even for just one season. Every chance is precious. Even teams that appear set up to contend for five or 10 years are delicate organisms. Lesson learned."
The Celtics probably would have fared much better had they gave up some of their young core for Kawhi. Sometimes, taking the risk is worth giving up current assets. Question is, will they hold to that philosophy when it comes to Anthony Davis?
Davis is on a one-year deal and will become a free agent in the summer of 2020. Currently, Boston has enough assets to get the deal done -- so long as they are willing to pay the price. Have they learned their lesson from the Kawhi sweepstakes, or are they going to tighten their grip around Jayson Tatum?