Did Celtics miss opportunity with Kawhi Leonard? How will it impact this summer?


Kawhi Leonard’s preposterous postseason play, which on Thursday night delivers the Toronto Raptors to an uncharted championship stage and Game 1 of the NBA Finals against the Golden State Warriors, has left a lot of Celtics fans wondering whether the team missed an opportunity to land a top NBA talent last summer.

This, however, reeks of hindsight.

For as fantastic as Leonard has been, reaffirming his status as one of the league’s elite two-way players, and leaving Doc Rivers on the borderline of tampering as he made Michael Jordan-level comparisons recently, it’s astounding to see how quickly many have forgotten just how much of a high-risk situation the pursuit of Leonard was seen as last summer.

Leonard was coming off a year in which he played only nine games due to a quad injury, and his inability to get back on the court — coupled by the drama it caused for the largely drama-free Spurs — raised caution flags on its own. That Leonard had only one year remaining on his contract and was seemingly ticketed for Los Angeles in the summer of 2019 might have been even more frightening for potential suitors.

Remember, too, that the Celtics were in a drastically different space. Jaylen Brown and Jayson Tatum had just unexpectedly propelled the Celtics to the fringe of the NBA Finals and there was unbridled optimism about Boston’s potential with the impending return of a healthy Kyrie Irving and Gordon Hayward.

League sources insisted at the time that Boston’s talks with San Antonio centered heavy on draft assets with the team likely not willing to mortgage their young talent for the many risks associated with Leonard.


Of course, we all know what happened the past eight months. The Celtics stumbled their way through one of the most disappointing seasons in recent memory. A team dripping with obvious talent proved unable to figure out how to properly harness it all. What’s more, Boston’s talent glut seemed to conspire against it and, when young players like Terry Rozier underperformed, all while Boston’s prime draft assets like the Sacramento Kings first-round pick plummeted in value, it was too easy to wonder if the team missed a sell-high opportunity.

Meanwhile, in Toronto, Leonard was spectacular, even as the team employed a load management strategy to preserve his health. The Raptors finished second in the Eastern Conference — nine games ahead of Boston — and Leonard landed on the All-NBA second team (about as close as he ever came to teaming up with Irving). 

It’s much too easy now to examine how the year played out and lament how Boston should have been more willing to include players like Brown and Tatum in a deal. Heck, even those players might not have been enough to sway Gregg Popovich and the win-now Spurs, who clearly valued getting an established four-time All-Star in DeMar DeRozan.

The Celtics simply weren’t in a position last summer where it made sense to roll the dice on Leonard. While Danny Ainge has said that players with only one year remaining on their contracts wouldn’t completely scare him away (we’ll get to you in a minute, Anthony Davis), it seems fair to suggest he’s treaded slightly more carefully with the likes of Leonard and Paul George given flight-risk potential.

Remember, too, that the Raptors were in need of a shakeup. Even with LeBron James fleeing west, Toronto was seemingly stuck in a rut of second-round playoff exits with that DeRozan/Kyle Lowry core and could more confidently take a flyer on Leonard in hopes of the jackpot they struck.

There is, of course, still the very strong chance that Leonard will flee for warmer climes this summer. The Raptors, knowing how this season played out, might still do the trade again knowing what exactly this postseason run has meant to the franchise in the bigger picture. They’ll cling to the hope that indelible moments like Leonard’s Game 7 winner against Philadelphia will force him to more strongly consider an extended stay up north.


The question that’s more prudent to ask from a Celtics perspective is whether the Leonard situation might encourage Ainge to be even more aggressive this summer in the team’s quest to land Davis.

Given that only one year remains on Davis’ current deal, the Celtics have to balance the risk that Davis might only be here one season. Maybe that’s not as much of a concern if a Davis acquisition encourages Irving to re-sign long term, ensuring the team isn’t left holding the bag if Irving was to bolt for a new situation and the team had to throttle down on the Davis pursuit.

The price tag for Davis will undoubtedly induce far more sticker-shock than Leonard did. New Orleans landing the No. 1 pick and the rights to choose Zion Williamson only further enhanced their leverage. 

Ainge must balance the risk. But the Celtics' situation has changed, too, in a year’s time. They cannot bring back the same core, and might need another reason for Irving to consider a long-term stay. They are far from desperate but it’s fair to wonder if the Leonard situation will make them think just that much harder about stomaching a bit more risk.

If nothing else, it’s a reminder that elite NBA talent does not become available that often — though maybe that’s changing in an NBA that will see a lot of laundry turnover this summer — and teams might simply have to be more willing to roll the dice given that windows seem to be closing faster than ever around the league.

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