Facing familiar story after playoff elimination, Raptors may be best turning to a familiar face: Kawhi Leonard

The Raptors took two notable steps to address their last handful of playoff losses to Cleveland. The first was a coaching change. Don't count on another. Darko Rajaković impressed in both the regular season and playoffs. He proved strategically adaptable against Cleveland and installed a motion offense that made the most of Toronto's limited shooting. He shouldn't go anywhere.

The second move? That one's a bit more repeatable. They traded for Kawhi Leonard.

We all remember how it went last time. Toronto, stuck in a regular-season rut with a LeBron-shaped playoff ceiling, broke up its Lowry-DeRozan pair to add Leonard on an expiring contract. James moved West, but Leonard proved productive enough to carry Toronto through a newly deep Eastern Conference and ultimately past LeBron's frequent Finals foe, the Warriors, to give the Raptors their first championship.

Leonard left soon after to sign with the Clippers, who are now under investigation for circumventing the salary cap to overpay him. Whether that investigation forces Leonard out of Los Angeles or not, the Clippers are already moving in another direction. They traded James Harden for Darius Garland at the deadline, then swapped Ivica Zubac for Bennedict Mathurin and picks. They're getting younger, preparing for whatever the next iteration of their team looks like. Leonard, who will turn 35 this offseason, no longer fits that vision.

Why trading for Kawhi Leonard makes sense despite the risks

Trading for Leonard this time around would probably be a bit more costly, at least in terms of picks. Ingram likely doesn't hold the trade value DeRozan did at the time, when the Spurs were just trying to remain competitive. The Clippers tend to prioritize championship equity, and a floor-raiser like Ingram is better-suited to a team like this year's Raptors, who are just trying to get in the dance. They'll want picks and they'll probably want Toronto's young big, much like San Antonio did. Jakob Poeltl was a worthwhile sacrifice for Leonard in 2018. Murray-Boyles is not. He will surely be untouchable in any Toronto offseason dealings unless perhaps they take a run at Giannis Antetokounmpo.

Hence, more picks. The Raptors have picks to spend. They control all of their own moving forward and, given Leonard's age, their picks deep into the future would probably appeal to the Clippers. Pinning down his exact value is tricky. He's coming off one of his best and healthiest seasons, but at his age, he's a risk moving forward. Regardless, there will be a market for him. Too many teams need wing defense and high-level playoff shotmaking. He's not netting the massive, four- or five-pick hauls that younger wings have been getting in recent years. It's probably taking multiple picks, though.

The Raptors will explore alternatives. They were linked to just about everyone at the deadline. Maybe they'll take another look at a buy-low candidate like Ja Morant. They'd probably love to add someone on Barnes' timeline, but young stars tend to be picky about markets, and few ever seem eager to cross the border. If, through some unlikely turn of events, the Nuggets broke up, a native Canadian like Jamal Murray would of course make more sense. He just probably isn't going to be available. Toronto, by virtue of its cold weather and the inconveniences of playing in another country, tends to have a hard time selling the sort of prime-aged, incredibly desirable stars they'd prefer to pair with Barnes on actually playing for them. The Raptors usually have to take some risks.

Leonard would still be a risk on a few levels. It's not just his age and injury history. He chose to leave Toronto. He wanted to play closer to home. Even if the Clippers made it clear they plan to move him, he still does have some agency, both through his expiring contract and the basic fact that having a moody Leonard on your team does you little good. If he has a specific destination (or a few) in mind, that complicates matters.

Of course, the Raptors could mitigate any concerns by offering a contract extension. Doing so would be tricky given how many bad contracts are already on their books. In a perfect world, they'd get off of Poeltl in the deal, but don't count on the Clippers or anyone taking him without getting assets for doing so. Maybe they could turn Quickley into a cheaper guard? If point-Barnes is a viable strategy moving forward, that could help. But getting off of Quickley's hefty contract wouldn't be easy either, and besides, you need as many ball-handlers as you can get to survive the 82-game grind. The Raptors would either need to get creative or potentially let Barrett walk after next season, a tough pill to swallow given his heroics against Cleveland.

The basketball fit is straightforward. The Raptors were an average half-court offense that lived in transition. Leonard tends to play slowly. If the young, athletic Raptors can generate easy points and Leonard can score the hard ones, their overall offense should soar. The combination of a great transition offense and an apex shotmaker tends to work out fairly well. That's how the Thunder are built, after all.

Leonard is by no means the defender he was at his peak, but he wouldn't need to be playing on this roster. Barnes is going to make an All-Defensive team this season. Murray-Boyles looks like he'll have a chance to do so down the line, and Shead and Walter were relentless against Cleveland. Leonard can scale up when needed, and he's still a stellar generator of turnovers, which would only help his younger teammates get out on the break.

There's an argument to be made against making any sort of short-window investment as a mid-tier playoff team right now. The Thunder and Spurs are so good that the optimal roster-building path is a long window, giving your team as many chances as possible at an unexpected outcome rather than betting it all on fewer, lower-odds opportunities. The very Warriors team Toronto beat in 2019 drew similar arguments at the time. The Warriors were better than the Raptors at that point, but the Raptors put themselves in a position to benefit from Golden State's injuries. That's the real debate here. You can waste an entire era waiting for the perfect move, or you can take your swing when the moment presents itself and let the chips fall where they may.

Barring something unforeseen, it is unlikely that a player better than Leonard becomes available to the Raptors in the near future. If one does, he will almost certainly cost more than the older Leonard would. The Eastern Conference is getting better. Indiana will be back in the mix next season. Charlotte, Atlanta, and even the 60-win Pistons should get better through sheer aging. There's no guarantee the Raptors can replicate this year's success a year from now.

In 2018, they didn't view replicating a season like this as a particularly desirable outcome. It's not enough to make the playoffs. The goal is to win there. Toronto's best path to doing so is the one they took eight years ago. The Raptors just suffered a familiar defeat. Now it's time for a familiar response.