Manning: Celtics Missed Out on Kawhi Leonard as Raptors reach NBA Finals

Boston enters the offseason in search of their next big move. It's unlikely they'll be able to outdo the Kawhi trade they had a chance to make.

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One 20-inch TV in the corner of a packed bar drew the eyes of an inspired Raptors fanbase optimistic they could challenge the King. In one swift motion, LeBron James scaled the court, threw up an off-balance layup and put Toronto down 0-3. Kawhi Leonard was not a dream then.

They fired Dwane Casey, the coach of the year. Even with James leaving the east, the prospect of the Raptors usurping what the Celtics accomplished in the next round seemed slim. Title-contending basketball in Toronto ended for the foreseeable future in one play.

The Celtics thought so too. Danny Ainge stood pat on a group returning Kyrie Irving and Gordon Hayward. Leonard hit the trade market, normally a develop that spurs Ainge into action. Especially when Leonard once made LeBron shiver watching him enter a Finals game. Four years later, he had an expiring contract and a mysterious injury that must have limited Ainge’s offer to a pick dump. The Raptors happily dove into the “risk” with their franchise cornerstone while Boston stayed away.

Ainge made a rare, drastic mistake to hold back in acquiring the best player in these NBA playoffs. Toronto is four wins from a NBA championship. They have a core that supersedes almost any roster the Celtics can bring back. Leonard looks better than Anthony Davis.

Leonard clinched Toronto’s first NBA Finals berth on Sunday in one of the great ECF performances of all time. He scored 27 points and grabbed 17 rebounds along with seven assists, two steals and two blocks. Exhausted and down 13, he flipped the game by nearly 20 points in under 10 minutes. He also overcame a leg injury in the series and held Giannis Antetokounmpo to 12-for-34 shooting.

The Celtics need to make the Davis trade to clean up a messy year and regain contention. If Ainge trades for him, it could require the C’s to move both Jayson Tatum and Jaylen Brown to limit how much else they give up, and to beat other offers.

A Davis trade will cost more than they would have paid for Leonard. It’ll carry the same amount of contract-year risk. Terry Rozier is no longer in the picture as a trade chip and the youth regressed this year. Kyrie Irving’s commitment is uncertain.

The caveat is that Leonard can still leave Toronto and the Warriors remain prohibitive title favorites. Given where the Celtics ended up, that uncertainty sounds better than the one the team faces. Leonard may be a hard personality to read, but any doubt about his on-court abilities was wild in retrospect.

Greg Popovich favored trading Leonard to the east. He made the most of Jakob Poetl, and DeMar DeRozan gave them a known commodity. Still, that being the best offer shows more teams than Boston overlooked Leonard. Toronto remarkably kept OG Anunoby, Paschal Siakam and pried Danny Green from the Spurs. It could become one of the best trades in NBA history.

Boston could have organized a package around Brown, Rozier and picks. If that didn’t break the fear of dealing with Ainge, Boston could have imagined a contract-year swap of Irving and Leonard with some filler. That Celtics team beats out this year’s, though it’s easy to include Irving in all these trades in retrospect.

What did not require foresight was seeing Leonard’s superstardom, capable of carrying a team. He won Finals MVP, two defensive player of the year awards and made two All-NBA First teams before any of his Toronto achievements. By missing on him, the Celtics cost themselves a chance at both a title and more flexibility than they currently have.