The Toronto Raptors just punched their first-ever ticket to the NBA Finals by defeating the Milwaukee Bucks in six games in the Eastern Conference Finals. Naturally, that makes one wonder if the Boston Celtics should have made a run at Toronto’s MVP, Kawhi Leonard.
In the summer of 2018, one of the league’s main storylines was where Kawhi Leonard would be traded to. The Boston Celtics, owners of the most expansive set of assets in the league, were one of the 2014 Finals MVP’s rumored suitors.
Unfortunately it was the Toronto Raptors that hit the jackpot by landing the “Klaw”. All it took was DeMar DeRozan and a draft selection (and Jacob Poetl) to land the services of a top-5 player who admittedly had questions surrounding his health.
The Boston Celtics have been in the conversation for just about every All-Star that demands a trade from his team in the past four years. Since the team swindled the Brooklyn Nets in 2013 and then the Philadelphia 76ers in 2017, their collection of assets has gotten them into the conversation for just about any player looking for greener pastures via trade.
Leonard is a free agent after this Raptors run is over, and that perhaps gave the Boston Celtics pause about trading their young assets. Danny Ainge was reportedly unwilling to part with Jaylen Brown or Terry Rozier for Leonard’s services. Looking back, it seems foolish that Ainge wouldn’t give up two guys that ended up being bench players for much of the year anyway.
That being said, you never know how trade assets are going to go. The San Antonio Spurs ended up getting a better haul after DeMar DeRozan fit alongside fellow mid-range specialist LaMarcus Aldridge. While Rozier and Brown seemed like a better haul back then, both are ticketed for hefty raises in the next two off seasons (Rozier is a restricted free agent this year while Brown is set to hit the market next summer).
Ainge likely always had Anthony Davis in mind as his big ticket free agent anyway. Davis has fewer health question marks now than Leonard had last year. Plus rumors that Leonard has wanted to return to play in his home state of California we’re rampant. Toronto had less to lose on a one-year rental than Boston did.
It’s tough not to think of Leonard in green and white and fantasize about what could have been. The Celtics are still in a good spot now though, especially if Toronto flames out and Leonard leaves the Atlantic Division.
Which is to say that while you could look back at what could have been, you’re better off looking forward.