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The Ka-Why Leonard is Staying Bracket: Wrapping up the Round of 32

It’s day two of the most important bracket ever created in the name of content. Let’s watch as Sean Woodley and Jay Rosales sort out the second portion of the first round to decide why exactly Kawhi Leonard is staying in Toronto.

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

We’re on to day two of the Ka-Why Leonard is Staying Tournament! Eight of our most cockle-warming bits of proof that Kawhi’s stay in Toronto will be extended beyond July have moved on to the Sweet 16. They’ll be joined by eight more today.

Some heavy hitters are in action today, including the number-one overall seed: everyone’s pal and master chef, Serge Ibaka. Will we see another 8-over-1 upset like we saw in the opening day of the tournament? Will Lawrence Frank ever recover from being snubbed by his white whale? Here’s hoping today’s action will at least produce some answers. Frank’s lingering existential dread is beyond our help.


(1) Tim Bontemps’ Podcast Clip vs. (8) “Pretty sad” JV got traded

SW: I am sick and goddamned tired of hearing about the Clippers, man. Jerry West is an old fraud, riding the wave of being the guy on the NBA’s logo — an honour he didn’t even earn! Bill Russell beat his ass like a dozen times in the Finals but couldn’t make it to the end of the logo interview process? Sure.

National media folks have been especially Clipper-happy whenever Kawhi’s future comes up. “Blah, blah, he’s likely to sign with the Clippers. They’ve built an amaaaaazing situation for him, how could he possibly say no to joining the illustrious Los Angeles Clippers,” the sources will say once every couple months. It’s exhausting.

So you can understand my excitement when I heard one of the plugged in national guys talk about how psyched Kawhi seemed to be about his situation and the team he’s currently playing for. I was on vacation in the Canadian Rockies when I caught wind of it and dropped everything to listen to the clip. Do you know how pretty the mountains are? How hard they are to stop looking at? I’m pretty sure a grizzly bear could be chowing down on my legs and I’d still be transfixed by those beautiful snow capped peaks. Word of Kawhi being, in Bontemps’ words, “happier than I’ve literally ever seen him,” though? Those mountains can go kick rocks.

Up against the most glee-rich piece of NBA media I’ve consumed this year is Kawhi’s sombre reaction to Jonas Valanciunas being shipped out in the Marc Gasol deal. Skeptics will say his “pretty sad” status after the deal might hurt the chances of him sticking around. To me, I see a man cultivating connections and laying down roots. Sometimes those roots get ripped out before a relationship blossoms. Someone leaving town in six months ain’t putting in the work to plant them in the first place.

As 1-8 match-ups go, this is a pretty good one, Jay. What are you thinking here?

JR: Not to get all conspiracy theory-like, but why didn’t this clip/tweet go viral? Why does Lawrence Frank attending Raptor games make headlines while Kawhi’s happiness remains a footnote? Could it be that we’re getting so many Kawhi-is-staying worthy quotes, that this is just another one? Or does NBA media have tunnel vision and already hell-bent on putting Kawhi in a Clippers uniform?

To your point, Tim Bontemps is one of the best in the game at getting player news. If he says Kawhi’s really happy, then damnit the man is really happy! Notice how the happy quote came after the sad-JV-got-traded quote? Actually, that’s not fair. I agree with you that there’s a lot to like about Kawhi making connections in the short time he’s been here. But I choose positivity over negativity everyday!

“Tim Bontemps Podcast Clip” advances

(4) Nurse quote about first meeting vs. (5) Quote about Nurse after he called out refs

JR: “First impressions are the most lasting.” — Proverbs.

More like Pro-Nurse, amirite? Not long after the “first photo”, Raptor fans had to play the waiting game again with Kawhi. This first meeting between new head coach and new superstar — not to be overly dramatic — had EPIC IMPLICATIONS towards how this season could go. With rumblings about this being a one-year layover before jetting off to Hollywood, the Raptors have basically been asked to pitch a perfect game - from training camp all the way to June. The fact that Nurse and Kawhi connected immediately was an early win for the franchise.

On the other hand, the subsequent quote was filled with goodies that validate the connection between Nurse and Kawhi. Admitting they’re on the same page in December is probably more indicative of his desire to stay then if they’re on the same page in July.

However, it’s been said that you never get a second chance to make a first impression. And Nurse nailed his. AAAARRRGGHHHH I can’t choose. You decide, Sean.

SW: This is the first time I’ve gone out and nailed the seeding. This is what a 4-5 match-up is supposed to be. Neither of these contenders are likely to make a run past the next round, but dammit if they aren’t going to grind it out for one-off glory.

I think I’m siding with the slight underdog here. Word of that first meeting going off smoothly was swell, but that came in the off-season. It was the coach-player relations version of muscle watch. I’d be alarmed if the reports weren’t glowing. Nurse coming to Leonard’s defense in the midst of a tough stretch of whistle for his superstar was the kind of coaching move that won’t get the accolades of a sweet out-of-bounds play, but it should. Superstar dynamics are tricky. As we’ve seen this year, their desires can be fickle. The best you can do as a coach is to support your star at all costs and hope it yields a strong bond. For Kawhi to go out of his way to shout out his coach for leaping to his defense is far more encouraging than a light summer chat.

You cool if we hand the W to the fifth-seed? Or should we take it to the poll?

JR: We are men of the people. Let’s see what the people have to say.

SW: And the people say:

“Nurse slagging refs in the name of Kawhi” advances

(3) Danny Green on Kawhi’s Comfort Level vs. (6) Masai’s Media Day Speech

SW: You’d assume based on their near decade as teammates, Danny Green knows Kawhi better than anyone else on the team — save for maybe assistant Jeremy Castleberry. So I trust this early-December evaluation of how Leonard was acclimating to Toronto livin’.

But for me, I can’t escape the feeling that Masai’s rousing media day address to the feeble and anxious Raps fans still licking the wounds opened by departed stars of old helped to kick-start Kawhi’s love affair with Toronto.

“Believe in this city, believe in yourselves,” implored Ujiri after a basic ass news reporter question about Toronto’s checkered past as a desirable destination. Perhaps Kawhi took that advice to heart, throwing himself head first into the culture of the city, and in the process, discovering a place he’d be thrilled to call home, weather be damned. Masai the pitchman, with that keen knack for making people believe in anything he says, is the great unmentioned recruiting tool in the Raptors’ back pocket. The speech that rung in the Kawhi era still sticks with me; what if it’s still sticking with Kawhi?

I think it’s clear where I’m leaning here, but what about you, Jay?

JR: I like where your head’s at. Masai took the F*ck Brooklyn approach to getting Kawhi on board. But I can’t shake the feeling that the comments from a close friend about his comfort level is more indicative than an attention-grabbing rallying cry in September. You could argue that Danny’s comments are also attention-grabbing, but if you’ve ever listened to his podcast, Inside the Green Room, you know he only speaks the truth. I think we might need a poll on this one, Sean.

SW: Oh, fine.

“Masai’s Speech” advances

(2) “Toronto has great energy.” vs. (7) “Toronto is like being in New York.”

JR: Everything Kawhi says in the “great energy” quote is positive and totally worth the second-seed in this region. He shouts out the fans, the city, his teammates, the coaching staff, organization, and, for good measure, doesn’t hate the weather. How could it possibly lose to a quote where Toronto is not the largest metropolis being mentioned?

Because one quote talks about how great it’s been and the other references about how great it’s going to be (it’s safe to assume that whatever he ventures off to see will be great).

Because one focuses on the past and present, while the other focuses on the future.

Actually, that all I’ve got. Unless you’ve got another reason for the upset, I’m just forcing the issue at this point. It’s the “great energy”, isn’t it.

SW: Yeah I’ve got no reservations about going chalk here. Had Kawhi been connected to New York for the last year and a half, or had he compared the feelings Toronto makes him feel to those Los Angeles engenders in his heart, then we’d be talking. But nah. This is a seventh seed that’s just happy to be here. It never should have had any illusions of defeating favourite. Moving on.

“Toronto has great energy,” advances.


(1) Serge Ibaka’s Existence vs. (8) Has Led Team in Scoring 42 Times

SW: Finally we’ve come to the number one overall seed in the tournament. To me, at least, Serge Ibaka has been the MVP of the Kawhi recruitment effort. Rather than being threatened by Kawhi’s presence, and timid when it comes to addressing the enormous elephant that is Leonard’s contract status, Ibaka has leaned into every little bit of the Leonard experience.

He’s embraced Kawhi, positioning himself — from the outside at least — as Kawhi’s closest buddy on the team, all the while staying unafraid to playfully put him on the spot.

Some might call Ibaka’s brazenness reckless. Keep in mind the quiet, respectful approach Kyle Lowry and DeMar DeRozan each took toward each other’s free agency decisions during their time together in Toronto. Serge is having none of that.

But maybe that’s the way to do it. Kawhi’s been treated like the egg a grade 11 physics class has to safely drop from a window. I’d theorize that Kawhi finds it refreshing — humanizing, even — whenever Ibaka broaches the subject everyone else wants to dance around. Kid gloves are not meant for handling grown ass adults. Ibaka has realized this.

On Tuesday, Ibaka dropped a perfect teaser for Season 2 of his acclaimed (by me) cooking and lifestyle show, How Hungry are You?

Our guy Jacob Mack covered it already. But I’ll expand. There’s a case to be made that those 15-seconds are the single greatest indicator of Kawhi’s intention to stick around we have yet come across.

This was a pre-taped trailer. There is clearly direction behind Kawhi’s prolonged silence. I’d venture to guess that clip won’t even appear in the actual episode when it drops. It is purely a vehicle for buzz. And Kawhi was party to all of it!

He and Ibaka are clearly buds. Even with Serge’s willingness to tow a potentially awkward line with Leonard and his future, he’s not an idiot. He’s not about to alienate a guy who willingly appeared on his web series — especially with the future of the franchise on the line, a reality Ibaka declared himself to be painfully aware of in that passage from Chris Mannix’s piece. There is absolutely no way Kawhi did not green-light this trailer to be published! This fact, more than anything, tells me he’s just as much in on the gag as Ibaka. Kawhi’s note-perfect, entirely expressive performance here says more than anything caught by a press mic or TSN camera this year. And it says, “I’m fuckin’ staying, dude.”

Oh, Serge is up against Kawhi’s very defined role as the leading man in the Raptors offense. This eight seed is going to get pumped, right, Jay?

JR: So, what you’re saying is, Serge is Duke and Leading Scorer 42 times is over-the-hill dads playing pickup at the YMCA. Gotcha!

Ibaka wins. There’s no debate here.

I hate to be a downer, but (warning: I’m about to mention something that might spoil the episode — or at least it’s validity as the one-seed) did you notice the change in camera angle between “coming back” and “next year”? It definitely looks like two different questions stitched together into one. Serge could’ve been asking if Kawhi would come back on his show, and ask a totally different question that happened to end with “next year”. Have I blown your mind? Are you re-considering the seeding? Or should I stop writing so late in the evening?

SW: Please stop talking. But hey, even if your no fun theory is accurate, Serge’s record of Kawhi recruitment is unimpeachable. He runs away with this one, and I imagine he’ll be a monster to try and knock out of this tournament.

Serge Ibaka” advances

(4) Norm Powell & Kawhi’s Mom are Pals vs. (5) Raptor on the shoe

JR: If there’s one thing I’ve realized throughout this bracket process, it’s that the Raptors really covered all the bases in keeping Kawhi happy. While Serge is out here doing the Lord’s work with Kawhi, Norm is using his San Diego roots to make an impression on Kawhi’s mom, Kim. I can see the late June conversation now:

Kawhi: “Mom, you think I should come back home and sign with the Clippers?”

Kim: “And leave behind those nice people in Toronto? Even that Norm fellow took the time to teach you piano!”

The Raptor (skeleton? logo? carcass?) in the shoe is pretty damn cool. Naysayers will argue that it should have been a full-bodied raptor, as opposed to a dead one. I personally would’ve been more impressed if there were only one shoe design, and that one had the dino theme.

I’m also a big fan of subtlety. Norm befriending Kawhi’s mom in an effort to win over her son is subtle. It’s a long game winner. Placing a logo that mimics the team you currently play for is not subtle, nor does it necessarily have staying power. In the end, I’m taking Norm. You with me on this one, Mr. Woodley?

SW: No! The shoe is really convincing to me. I know it’s one of just six different colourways that’s embroidered with the raptor skeleton, and I understand that it’s only on the insole. But shoes are expensive to make, man! It would have been really easy to not include the bones from the first Dr. Allan Grant scene in Jurassic Park in any of the shoe designs. But it’s in there anyway. It’s gotta be the shoes moving on, for me at least. But we’ve reached yet another stalemate, so we’ll let the internet decide.

“Norm and Kawhi’s Mom are Pals,” advances

(3) Raptors go all-in at the deadline vs. (6) Snubbing Lawrence Frank

SW: Toronto could have hung tight at the deadline, allowed JV to return from injury, and incorporated him back into the match-up dependent rotation Nick Nurse had constructed early on in the season. There wasn’t anything exactly wrong with the roster the Raps started the year with. But there was just a little something missing from Toronto’s mix.

Masai Ujiri and Bobby Webster moved all the way in with the Kawhi deal in the first place. To leave holes unattended to come deadline time would have been a half-assed way to double down. So instead they used their full asses, and swung the deal for Marc Gasol, injecting the lineup with an all-time good big man passer whose skills should play up against any of the best teams in the East. Not only did the move boost the Raptors’ ceiling, making it more likely that the team will reach the magical NBA Finals threshold that could make Kawhi’s decision to stick around that much easier. It also showed Kawhi just how bold the front office is willing to be in the name of chasing rings. That’s quite a quality to have in a partner!

Toronto’s deadline maneuvering is matched up with the following interaction, detailed by The Athletic’s Sam Amick in his piece documenting the thirstiness with which the Clippers are lusting after Kawhi this year. This franchise creeps me the hell out.

As much as it is awesome that Leonard snubbed Frank, who no doubt was ready to tamper his ass off had Kawhi stopped to chat, I have a hard time advancing this scenario into the Sweet 16. It’s that smile Amick alludes to, from his next-day debrief with Leonard, that gives me pause. I don’t know how to read it. Is he smiling because of a snub job well done? Or could it be a knowing nod to Amick that he knew exactly who he was ignoring out of fear of the T-word? The doomsday scenario is that he was smiling merely thinking about the idea of playing for the Clippers. I’m going with the three-seed here, Jay. What are you thinking?

JR: In the battle to keep Kawhi, Serge and Norm are working the front lines andNurse and his staff are load managing on the seas. All the while, Masai and Bobby Webster are strategizing at base camp.

Look no further than opening day against Detroit two seasons ago to see the growth of this roster. On that day the following guys played over 20 minutes: Jonas Valanciunas, DeMarre Carroll, Patrick Patterson, and Cory Joseph. Now compare that to Sunday’s game, also against the Pistons and you’ve got Fred VanVleet, Danny Green, Jeremy Lin, Marc Gasol(!), and Kawhi freaking Leonard(!!). The Clippers simply can’t field a roster as good as what the Raptors have. The Clippers could have Lawrence Frank lay rose petals in front of Kawhi’s path and he’d still be treated better in Toronto. The Clippers could pay every single person in Los Angeles to beg Kawhi to return home and the Raptors would still have a country to support him. The Clippers are... The Clippers. They do not strike fear. It’s no surprise Frank’s presence went unnoticed by Kawhi.

Masai Ujiri demands he be noticed simply by walking into a room. Just like Raptors management, I’m all-in; the three-seed moves on.

“Raptors go all-in at the deadline” advances

(2) Load Management vs. (7) Willingly Stayed in TO over All-Star

JR: Can you honestly remember the term ‘load management’ being used before this season? Not only has it become synonymous with Kawhi Leonard, but it’s recently being used — the term and the act — by other teams (Joel Embiid and LeBron James come to mind). This has got to be the strongest 2-seed in the field.

I’ll admit I was a little giddy to hear Kawhi came straight back to Toronto after his All-Star appearance.

The extended time off after the All-Star Game could have been spent in the nice California weather, but his immediate return to Toronto signified two things: 1) He’s really okay with the weather, and 2) He really didn’t want to lose to the Spurs again.

All that being said, this is an easy chalk win for me. Toronto’s careful management of Leonard’s load moves on. Wouldn’t you agree?

SW: Yeah. Look, Kawhi might be a bit of a hypochondriac. But who are we to judge! And who are we to discourage the Raptors from adhering to Kawhi’s needs if he wants to be a bit persnickety about how often he plays. He’s awesome; the Raptors are in the business of keeping the awesome player in town. Not managing his load would be borderline negligent. The Spurs obviously did something pertaining to his health that he did not appreciate; Toronto should be avoiding making the same mistakes at all costs — even if it does look from the outside like they’re giving him preferential treatment. Guess what, the 27-point averaging Finals MVP who happens to be the most talented player in franchise history has earned a little special attention.

That Toronto has been so conscientious when it comes to Kawhi’s health is a major feather in their cap. By joining any new team this summer, Kawhi will be taking a risk, and entrusting his health to a brand new, unknown medical staff. Who knows what kind of creepy doctor shit the stalker ass Clippers might be up to. Signing with the Clips might doom Kawhi to having his torso spliced onto Chuck the Condor’s legs at Steve Ballmer’s behest.

I, too, found it encouraging that Kawhi opted to spend the All-Star break in T.O. But I also don’t really view Kawhi as much of a vacation guy, so I’m not sure how much to really read into it. I’d like to spend a week in the home of Jerk King, too.

Load management may be a phrase to snicker at, but it’s gonna be a powerhouse in this tournament. Load management vs. Serge Ibaka in the Elite 8 is the heavyweight match-up we deserve.

“Load management” advances

Come back on Wednesday as The Sweet 16 unfolds! Here’s a look at the bracket through round one.