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Looking ahead to the good, bad, and ugly of the Raptors’ trade for Kawhi Leonard

Let’s review the good, the bad, and the ugly future timelines of these Kawhi Leonard-led Toronto Raptors.

NBA: Toronto Raptors at Brooklyn Nets Brad Penner-USA TODAY Sports

The Raptors have completed a massive trade that will see the most talented player to ever don a Raptors jersey come to Toronto.

But, wait, will Kawhi Leonard actually come to Toronto? According to NBA Reporter Chris Haynes, Kawhi has “no desire” to play here. And it’s not like DeMar is too pleased either, feeling that Masai Ujiri and the Toronto front office lied to him about whether he’d be traded. (This is an undiscussed side effect of running such a tight ship. You may have to lie to your players to make sure news doesn’t come out of their camp).

And does Masai actually want to keep Leonard? Could this just be a savvy businessman spotting an arbitrage? A prelude to the long promised “culture change” (more on that later).

With so much strangeness rolling around I thought I would dive into a Clint Eastwood-inspired look at what this trade might do to the future of the Raptors. (Plus I had been working on one of these based on what assets might be in an actual trade — suffice it to say, this was closer to the Good than the Ugly of those scenarios).

The Good

Kawhi gets over his petty “desires” and decides to rehabilitate his image by balling out hard in the 6ix. He and Kyle Lowry establish a strong working relationship — with even a dash of the “straight man/acerbic clown” pairing that Kyle and DeMar DeRozan had.

Pascal Siakam and OG Anunoby both take leaps, which justifies Masai keeping them both out of the deal. The net effect is a Raptors team that not only wins the East, but gives Golden State a legitimate battle in the Final. (They lose in five games, instead of a clean sweep.)

Kawhi decides to take the max-money extension the Raptors can give (knowing that he can always force a trade later if things stall out in the future). Toronto looks ahead to a future of building around a core of Kawhi, OG, and Siakam. Not bad at all.

The Bad

Kawhi plays, but not more than 60 games. He shows some flashes of the player he was, but only flashes, as a reluctance to hurt himself for this Raptors team, and his unhappiness, shines through.

Kawhi ends up unable to go in the playoffs — claiming he’s having Zaza-inspired flashbacks — and the Raps bow out in five games to the Wizards. The only bright side here: at least it’s not another Cavaliers sweep.

At the end of the year, Kyle Lowry wants out, and the Raps have to trade him for pennies on the dollar. Then, a year later, Toronto is just good enough to keep the protections on the pick from triggering and they’re out the pick.

The Ugly

Kawhi refuses to report to Toronto. Instead he spends the rest of the year rehabbing. He gives the Lakers, and only the Lakers, his medical records, and then signs the $140 million max with them in the off-season, giving up the $50 mil from a sign and trade scenario as a final FU to anyone in the league who thought they could keep him from what he wanted.

Lowry forces his way out of Toronto in a messy-mid season divorce. Meanwhile DeRozan savagely rips the Raptors from afar. Those actions, combined with Kawhi’s refusal to report, brings back the “nobody wants to play in Toronto cloud” with a vengeance.

Jakob Peoltl blossoms into a 15-10-2.5 blocks a game guy for coach Gregg Popovich — and becomes one of the league’s most versatile defenders in the middle because of his speed. On the other side, Masai’s rebuild starts slowly as OG and Siakam regress under too heavy a workload — and after he seemingly misses on his 2020 first rounder Masai is fired.


Whew, that is the darkest timeline. Fortunately, we have a bonus one on offer, which is actually my secret hope. Buckle up for...

The Whacko

In this world, Masai sees what everyone else sees — a star player who is hellbent on heading to Los Angeles. But unlike the Spurs, Masai doesn’t feel the need to bludgeon the Lakers in a deal.

In this world, the trade was just the first in a two-step process. Ujiri’s real goal is to accelerate Toronto’s rebuild, which means flipping Kawhi to the Lakers.

Or maybe: the Clippers.

You see, there’s been enough chatter out there that Kawhi isn’t as hot on the Lakers as he once was, because he doesn’t want to be “LeBron’s little brother.” This might be BS, and, of course, the Clippers, will never ever be the Lakers.


Could Steve Ballmer and Doc Rivers sell Kawhi on the idea of him going toe-to-toe with LeBron for the city’s supremacy? Could Kawhi be seduced by playing in the same building, and city as LeBron, but making, for as long as he was there, the blue and white of the Clips the cool colours?

Do the Lakers want to take the chance that if the Clips get Kawhi for a full season they can sell him on the idea that the extra $50 million they could offer him in the off-season is worth the Laker’s legacy?

I think it’s possible the Clips are a legit dark horse. That gives Masai some leverage.

He’s still not getting Brandon Ingram or Lonzo Ball, plus Kyle Kuzma, plus picks with that leverage, but what about Ingram, plus Luol Deng’s awful contract, plus Summer League MVP Josh Hart, plus a future first (likely near the end of the round)? Perhaps Toronto takes on Rajon Rondo, or Lance Stephenson and gets out from under Norman Powell’s contract to boot?

Or maybe the Clips make a legit offer — Canadian wunderkind Shai Gilgeous-Alexander plus Tobias Harris, and a lightly protected future first?

Both teams have an incentive to deal — if (when?) Masai engages it’ll become obvious that he’s going to trade Leonard to either one of them — for the best, reasonable, return.

Either deal makes the Raps young core more interesting, gives them more future assets, cleans up the cap, and makes the future clear: find the best trades for Kyle Lowry and Serge Ibaka, either this season, or more likely, next year when they are expiring contracts.

A move like this would shatter the Raptors chance to make a run now — but the Warriors still exist now — and maybe with an Anunoby-Siakam-and say, Ingram core, still great depth, and $20+ million to chase any stars that shake lose (Draymond Green is the consummate underdog, and as a Michigan guy might not have any weird anti-Canada biases). Toronto could suddenly seem just as young and interesting as the Celtics and the Sixers.

Your move, Masai.