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The Ka-Why Leonard is Staying in Toronto Bracket: The First of 32

Everybody likes brackets. Everybody wants Kawhi Leonard to stay in Toronto. With this in mind, join in as we settle the Ka-Why Leonard is Staying Tournament.

Toronto Raptors v San Antonio Spurs Photo by Ronald Cortes/Getty Images

We all know Kawhi Leonard is definitely staying. It’s hilarious think any other outcome is even possible this summer. The Clippers can talk a big (and creepy) game, and project themselves as this grand franchise just waiting to steep itself in newly-accrued history, but they’re still the goddamn Clippers, man. The Knicks? Ha. Brooklyn? We all know how to fill in that blank. The Lakers are the exact kind of self-aggrandizing shit show Kawhi seems to despise. It’s gonna be Toronto. It just is.

But for a second let’s just pretend we don’t have such accurate foresight. A lot of things have happened to and near Kawhi Leonard during his first (of many) season(s) in Toronto, each of which helping to build the the “He’s Staying” case. But which screen-grab, quote or fact of life has been the most convincing piece of evidence pointing toward Kawhi’s decision to stay put in Toronto? That’s what we’re here to determine.

Rather than exploiting teens and pretending like we know what collection of unpaid labourers will triumph over all the other unpaid labourers, Sean Woodley and Jay Rosales are here to talk about the cold hard facts behind the soon-to-be handsomely paid member of the Canadian work force. In the The Bracket of Ka-Why Leonard is Staying, 32 nuggets of information will be pitted against one another, with just one being chosen as the most convincing reason for Kawhi’s impending decision to become a dual citizen.

We begin with the first eight match-ups of the round of 32.


(1) Celebrating Pascal’s Winner against Phoenix vs. (8) All-Star Game Dancing

SW: There was a time early in the season when Kawhi wasn’t even sitting courtside on his load management nights. That wasn’t a problem, per se — by all accounts those absences from the bench were in the name of treatment and stuff — but it was still a little jarring! With word of the Clippers being hella creepy stalkers lurking in the bowels of the arena, and the general fan base-wide paranoia over the state of Kawhi’s day-to-day mood, it’s always been just a little more comforting to see him in the periphery of the screen than not when he’s out.

Pascal Siakam’s winner against the Suns came with Leonard out for rest. And it was one of the first times I can recall seeing Leonard exude genuine glee in response to something the team had done. It was so exciting, in fact, that is inspired this dumb idiot to do this dumb tweet.

Kawhi dancing at the All-Star game wasn’t really Raptors-related, which explains the low seed. But damn it was fun to see the NBA’s biggest recluse attempt to show that he’s open to exuberance, however much his dance move looked like an NBA 2K glitch. My girlfriend would also like me to mention that this was the moment she realized that Kawhi was worth fully investing in. Are the Raptors responsible for cracking open the shell Kawhi was once encased in? Who’s to say. What say you, Jay — is there an upset in the works here for you? Or are we going chalk?

JR: The effort it probably took for Kawhi to utilize his dance software — on a national stage and in the presence of his peers, no less — calls for an upset scare. But I’m going chalk with this match-up.

He could be celebrating because the Raptors won. He could be celebrating because his friendship with Siakam is growing and he’s happy for his buddy. He could be celebrating because Nurse may have unlocked another end-of-game play that, in turn, opens up the floor for Kawhi. He could be celebrating for a multitude of reasons. But he’s celebrating — and staying (at least in the bracket for another round).

SW: Yep, I’m with you. Pascal Siakam is cool. Kyrie Irving and KD are not. I’m picking the clip that does not feature the latter wo.

“Celebrating Pascal’s Winner vs. Phoenix” advances

(4) KLOE & The Klaw: Best Pals vs. (5) LA Media is Bad

JR: I was recently on the Rolling Thunder podcast with Ben Mertens, and asked him how Oklahoma City was able to get Paul George — the supposed one-year rental who everyone expected to sign with his hometown of Los Angeles (sound familiar?) — to re-sign with the Thunder. He said it basically boiled down to two items: 1) the culture that Sam Presti and co. had built; and 2) Russell Westbrook. From a culture standpoint, refer to the entire “External Factors” region. As for Westbrook, Mertens mentioned Westbrook’s ability to relieve some of the pressure/workload from George made his decision to re-sign much easier. That’s where Kyle comes in. What started as “I don’t know if I’ve spoken to him” in late July, has blossomed into numerous examples of KL (x 2) showing their budding relationship.

Meanwhile, In Kawhi’s first trip to his hometown as a Raptor, an L.A. reporter asked a silly question, hoping it would lead to Leonard reminiscing about his Los Angeles roots.

Kawhi wasn’t having it. “Kawhi’s not feeling Los Angeles” doesn’t roll off the tongue but the effect is just the same. I’m leaning K.L.O.E. (x 2) in this match-up. What say you, Sean?

SW: Yeah, I think I agree. I am certainly thankful to the poor bastard who decided to ask Kawhi about Christmas. Any bit of contempt for the LA media experience is helpful. But those interactions with Lowry have a playfulness you just don’t get between two guys who are merely co-workers forced to figure it out together. Lowry once called his buddy DeMar DeRozan out on camera for his inability to properly add.

Kawhi calling Kyle stupid is basically the same thing. A four-seed may have been too low here.

(4) “KLOE & The Klaw: Best Pals” advances

(3) Budding Friendship with OG vs. (6) Applauding Boucher’s Chase-down

SW: By the end of last year, OG Anunoby was unfairly drawing comparisons to Leonard. It was crazy at the time, and has been proven even more crazy now that the actual Leonard is on the team and we can see the two side-by-side. OG rules, but come on, man.

It’s nice however, that the two quietest Raptors are in touch with each other’s senses of humour, and that Kawhi seems willing to share his bounty of wisdom.

Kawhi getting jazzed for the Raptors’ garbage time MVP’s chasedown block near the end of the very fun Pelicans blowout on March 8th isn’t surprising, really. You’d have to be clinically dead to not get pumped for that shit. The smile-clap combo, though? That’s a rare one from our guy.

Whatcha thinking here, Jay? The tutelage of OG, or the genuine excitement for a guy Kawhi may never share the floor with in another game this season?

JR: Add me to your list of people unfairly comparing OG and Kawhi. Over the last 12 months, I’ve used the terms Kawhi 2.0 and Kawhi Lite to describe OG Anunoby. The problem with the OG-Kawhi friendship is that they’re TOO similar. Like, are they actually friends? Has anyone seen them speak real-live audible words to each other? What if they don’t like each other, but OG quietly follows him because he’s expected to become the next Kawhi? Call me crazy, but sign me up for genuine happiness for the 14th man. Sign me up for any smile-clap combo from Kawhi. Sign me up for any emotion from Kawhi.

SW: I am such a sucker for any instance of Kawhi cheering on the lads that I have no choice but to agree with you here.

“Applauding Boucher’s Chase-down” advances

(2) The Lingering Hand vs. (7) The First Photo

JR: The last time Kawhi was in a Spurs uniform at his peak superstar powers, he was single-handedly destroying the Golden State Warriors in Game 1 of the 2017 Western Conference Finals. Fast forward a year and a half and Kawhi finally gets his revenge — albeit in a late-November game with no Steph Curry. After the victory, as if to signify in his own quiet way, “I got us,” Kawhi’s giant right hand touches (caresses?) the Raptors logo.

After the dust settled from the trade, excitement started to dwindle as Raptors fans waited for a tweet/quote/rumour/ANYTHING from Kawhi. Then, it happened. A simple photo, taken inside the Raptors’ practice facility, with Bobby Webster to his right, and Masai Ujiri to his left, posed Kawhi Leonard and… wait a second… are those... his teeth?!? Is Kawhi smiling??? As this entire bracket is outlining, the “Kawhi is Staying” phrase has been used a plethora of different ways over the season. But the very first time it was used, is something quite unforgettable.

I gotta say, if that hand didn’t linger... if it was more of a tap... I’d be calling for an upset.

SW: Ugh. I wanna go with lingering hand here. I really do. It’s delicate and chilling and makes my stomach flutter just the tiniest little bit. He didn’t put the hand ON the logo, though. He could just as easily have been gaining leverage as he walked around the corner. It’s just not conclusive upon review that he’s reaching out to graze the logo of his new beloved squad, which pains me deeply to admit.

That first photo with Kawhi… man. I remember that thing coming across the TL so vividly. It was proof that all of it was real; that Kawhi Leonard was, in fact, a Toronto Raptor. It was also the first opportunity we all got to dunk on Chris “He’s Not Coming” Haynes. After that week of uncertainty and the slightest sense that it could all fall apart, that photo gave us permission to cast aside all reservations. I badly would like to know who took it so I can send them a card.

We’ve reached an impasse, so it’s time for our tiebreaker protocol to get its first bit of work. AND THE VAGUE TWITTER POLL SAYS:

“The Lingering Hand” advances.


(1) The Five-Year Max vs. (8) “Snow is nice to look at.”

SW: Not much in the way of fanfare here. The Raptors can offer Leonard more money than anyone else — five years/$190 million vs. four years/$141 million from teams without his Bird Rights. For a guy with an injury history, that is not nothing, even if the supermax rules offer diminishing returns for guys who are gonna be rich as hell no matter what version of a max deal they sign.

Pitted against the financial advantages of the Raps’ position is the possibility that maybe Kawhi just really likes to look at snow. I get it. It can be pretty as hell. I personally am a winter over summer guy. Why is it so crazy that Kawhi might be one too? In addition to this pull quote from NBA All-Star weekend’s media day, there’s at least one other instance of Kawhi referring the natural beauty of fresh-fallen snow back when those dumb LA reporters kept asking him about the weather and Christmas.

This is a tricky 1-8 match-up in a loaded section of the bracket. Jay, are you more moved by money or snow’s magical properties?

JR: As you’re about to read in the next match-up, Kawhi really purchased TWO multi-million dollar homes since joining the Raptors. You could look at that two ways. 1) He has so much money, it doesn’t matter if he loses several millions on his next deal, or 2) He needs to recoup some of that dough and go where the cash flows. On the flip side, Kawhi’s been seen multiple times wearing un-winter-like clothing during very winter-like weather. He may not only love the snow but, dare I say, loves the cold! Have I just convinced us to go with this tourney’s first ever 8-over-1 upset? (Or did you screw up the seeding again?)

SW: No! I was on the fence, and you’ve talked me into it. The supermax doesn’t seem to matter to anyone who matters. Kawhi could have gotten an even more lucrative deal had he stayed in San Antonio. But San Antonio does not have snow, at least not a reliable amount of it for five months of the year. Toronto does, thus, he is staying.

I imagine Kawhi appreciates the uniqueness of every single snowflake. He is, after all, a one-of-a-kind character among NBA superstars himself. Now, for him and Serge to take a trip to Ottawa for a canal skate and maple taffy to really seal the deal.

“Snow is nice to look at,” advances

(4) Bought a house in Toronto vs. (5) Raptors Hire Castleberry & Handy

JR: Kawhi buying a home, as opposed to renting one, is definitely bracket-worthy. The fact that he ended up buying another home in California — albeit, 2.5 hours away from Staples Center — steals a bit of thunder from the Toronto purchase. It’s ot so much that he bought a home in California, but that he’s so rich he purchased two homes inside 6 months. It just seems like he a thing he does. It’s good-not-great news for the Kawhi-is-Staying crowd.

What was great news was the hiring of Spurs Assistant, Jeremy Castleberry, and Player Development extraordinaire, Phil Handy.

Tired: Bringing in players that compliment Kawhi’s style of play.

Wired: Bringing in COACHES that a) Kawhi knows and respects, and b) have experience helping superstars develop (like Blake Griffin, LeBron James, Kyrie Irving, etc.)

For my money, the Assistants win this match-up.

SW: Another example of me over-seeding something. The house thing is nice and certainly doesn’t hurt, but even in the insane Toronto housing market, an NBA star buying a new pad is no more harmful to the wallet than when I sometimes level up and get a king-size chocolate bar — the difference being that I can’t resell the chocolate bar and make a killing if I decide after eating it that I’d like a different one with more nougat. But Kawhi will not be selling his place in our fair city! Because he’s staying! And the additions of Castleberry and Handy probably played a role in that. Easy win for the 5th-seed.

“Raptors Hire Castleberry and Handy” advances

(3) Japan Loves New Balance vs. (6) Pascal Siakam is really good now

SW: Kawhi signs with New Balance — one of, if not the most popular sneaker brand in Japan — and the Raptors find their way into a pair of preseason games in Tokyo just before Leonard’s first full season with a signature New Balance shoe? I’m sure it’s just a coincidence.

Up against Toronto’s conveniently timed trip abroad is the ascension of likely Most Impoved Player, Pascal Siakam. Kyle Lowry is amazing, but he’s turning 33 next week. While playing with him is certainly a short-term carrot to dangle in front of Leonard, Siakam’s transformation into a fringe All-Star with ludicrously good on-court impact metrics give the Raptors a legit dude to sell Leonard on teaming up with for the long haul. No, he’s not one of the other superstar free agents in Leonard’s class, but he certainly seems less odious to play with than the Durants, Irvings and Butlers of the world.

This is a heavy-hitting match-up Jay. I’ve done a horrible job seeding this thing. But someone’s gotta move on. Who ya got?

JR: Similar to how amateur bracket pickers say things like, “I don’t care who, but you’ve got to have a 1-seed make the Final Four”, I think there has to be a business reason for Kawhi to stay. The Japan-New Balance story fits the mold.

Siakam should be the winner, but we have enough basketball reasons for Kawhi to stay. Besides, Kyle and Serge are going to carry the load as Kawhi buddies in this bracket.

Give me more New Balance!

SW: The New Balance thing definitely raises my eyebrows. And had Kawhi been featured in the Raptors’ promo video announcing the Japan preseason games — like Marc Gasol was — I would be picking it to win. But man, Pascal Siakam is so freaking good now. If the NBA weren’t so predicated on good players teaming up to win stuff, I’d be less inclined to choose his growth as the winning pick here. There’s a world in which Siakam gets ranked higher on SI’s Top-100 next year than DeMar DeRozan ever did; he’s a real recruiting tool, so I can’t choose the shoes. But maybe the blind poll will.

“Pascal Siakam is Really Good Now” advances

(2) The Raptors Play in the East vs. (7) Kawhi is the Antidote to Paul Pierce

JR: Quick, name a team that’s tanking. Congratulations, you’ve likely named a team from the East who will gift-wrap three or for wins for Toronto every year. If you’ve got a chance to only play the Warriors twice a season instead of four times, wouldn’t you take it? Do you think Kawhi would have as many opportunities for load management if he played in the West? All signs point to Leonard being a smart (and fun) guy. The East has just enough good teams to challenge him, yet a ton of easy teams against whom he can expend minimal energy. Kawhi definitely has ‘it’. You know, that thing Paul Pierce famously claimed the Raptors lacked.

The same ‘it’ that New Balance claims Kawhi possesses. If anyone can confirm that it was Kawhi’s idea to include that line, this instantly becomes a tournament favourite. Alas, it was probably the work of a Production Assistant, so I’ll stick with the 2-seed. Would you agree, Sean?

SW: I’d like to believe that Kawhi is a fan of poetry in sports. I don’t know how much he’s followed the Raptors since they got good; he was, after all, off winning Finals MVPs and what not during the early years of this run by the Raptors. If he is in fact unaware of Toronto’s past run-ins with Pierce, he’s done a really bad job of showing it. In addition to that convenient screen grab from the New Balance commercial that we’re shoehorning into this argument, there was the whole matter of Leonard doing something Pierce also famously did against the Raps in the playoffs.

There’s an argument to be made that Kawhi’s been fashioning himself as the Raptors’ antidote to all that has let them down in the past all season long. I would like to believe it. But man, the East sucks so much ass. It’s gonna be hard to knock off the favourite here.

“The Raptors Play in the East” advances.

Come back for the second half of the Round of 32 on Friday!