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The Ka-Why Leonard is Staying Bracket: Time for the Sweet 16

Sixteen pieces of infallible proof of Kawhi’s intentions to stay remain. Today Sean Woodley and Jay Rosales narrow it down to eight.

NBA: Toronto Raptors at Cleveland Cavaliers David Richard-USA TODAY Sports

Since we first released the this here content last week, the He Stay momentum has only gathered. National media, fans, the team itself — all seem a little more optimistic about Kawhi’s future plans these day. Are we responsible for speaking all these good vibes into existence? Probably. And you’re welcome.

The 16 remaining bits of evidence that Kawhi’s ready to lay down Canadian roots will be trimmed in half today. Sean Woodley and Jay Rosales, take it from here.


(1) Celebrating Pascal’s Winner vs. Phoenix vs. (4) KLOE & KLAW: Best Buds

JR: Kawhi celebrating his teammate’s game-winning bucket would probably win this match-up if we polled every single Raptor fan. Kawhi cracking jokes with Kyle Lowry would probably win this match-up if we polled Raptors Twitter. To me, this boils down to whether you think Kawhi’s stay-worthiness™ is about enjoying the culture that’s built on the court (Pascal game-winner) or off it (Kyle = best bud).

Sean, I’m going to contradict what I said on your podcast earlier this week and go with Pascal. I know I was quite vocal about the KLx2 relationship being a favourite in this region, but there’s something to be said about how happy Kawhi was with Siakam’s buzzer-beater. Many teammates have lauded Kawhi’s behaviour off-camera, claiming he actually is a fun guy. The fact that some of those moments are caught on camera with Kyle shouldn’t really change that stance.

Re-watch the Pascal clip.

That is unadulterated, unbridled, and prior to this season, unbelievable joy glistening off of Kawhi. He first congratulated Pascal then looked like he wanted to spread more love. Give me that Kawhi all day long (or at least for another round). What do you think, Sean?

SW: I was pretty sure I was all in on the Kyle-Kawhi relationship in this showdown. But congratulations. You have moved me off my spot like you’re Kawhi and I’m Paul George. Kawhi’s shown glee on the sidelines a bunch this season, but you always remember the feeling the first time you experience something new.

Kyle and Kawhi getting along is fantastic! But both seem like guys who don’t necessarily need to be chummy with teammates in order to stay focused on winning games. I mean, think about how surly Lowry seemed early in the year in the wake of DeMar DeRozan getting shipped out, and how the Raps started 20-4 anyway. And not to bring too much gloom to the conversation, but Lowry is 33 and just over a year from the end of his contract. If Leonard is to sign on long-term, Lowry likely won’t be here for the majority of it. Leonard’s giddy responses to team success is probably more crucial than his friendship with Lowry. Though I will not object to the two engaging in more goofiness for the cameras.

“Celebrating Siakam’s Winner” advances

(2) The Lingering Hand vs. (6) Applauding Boucher’s chase down

SW: I was a noted skeptic on the topic of the Lingering Hand last week; so much in fact that it only narrowly survived an upset via the mercy of the blind poll. But I’m not the type of person who’s so married to my opinions that I can’t be swayed by convincing evidence to the contrary.

In the week since we posted part one of the bracket, Brian Windhorst said something that’s made more of a believer out of me.

I’m sure Windhorst will be very okay with me quoting something he said on a podcast and putting it in a blog. He actually really likes when people do that. Go back and listen to the episode of The Hoop Collective from which this passage came. The contents of that little spiel are encouraging enough. What really got me, though, hesitation in his voice when cutting off Tim McMahon, who remains confident that the Clippers are the leaders for Kawhi this summer.

Windy knows shit, man. More importantly, he’s known for knowing shit and not really spilling the full can of beans until the last possible moment (see soup, chicken tortilla). Then when you consider Windy’s track record of being on the trail of stories well ahead of time (think Jimmy Butler vs. the Wolves), you’d be a damn fool to wave away that clip as mere off-the-cuff speculation.

Maybe Kawhi is doing pretty OK in Toronto. Maybe he’s so OK with Toronto, in fact, that he feels compelled to place his hand upon or near the logo at any opportunity that presents itself. What if this captured footage of Kawhi’s hand grazing the wall adjacent to the logo is a regular occurrence, borne out of his adoration for the team that has treated him so darn well.

I’m just as thrilled as everyone else that Kawhi got jazzed up when Chris Boucher proved himself once again to be the garbage time king of the Raptors. I’m even more pumped up by Windhorst’s vague allusions to his happiness with the franchise. I’m a Lingering Hand stan. What about you, Jay?

JR: I can’t gush over Kawhi’s joy for a Siakam buzzer-beater then NOT do the same after showing similar emotions towards Boucher. In fact, that’s probably even more noteworthy -- Kawhi cares about this entire team, not just a few individuals. When you look up and down this entire roster, is there a single person that’s unlikable (on or off the court)? Even the coaching staff is so damn likable. On top of all the many reasons discussed in the bracket, do you really think he’ll leave for L.A. and play with noted shit disturbers, Jimmy Butler or Kevin Durant or Kyrie Irving?

Sorry, Sean. I was going to follow that up with, “...and that’s still not good enough to top the lingering hand.” But I think I just jedi mind-tricked myself into picking the Boucher clip. I think we need a poll.

SW: Goddamn. Upset city.

“Applauding Boucher’s Chase Down” advances


(8) “Snow is nice to look at.” vs. (5) Raptors hire Castleberry & Handy

JR: Oh, this one’s juicy. Does the Cinderella run continue through to the Exceptional Eight? (Sorry, ‘Elite’ was taken) Or does her run end because she left her slipper at the Castle(berry)? Alright, I’ll just see myself out.

If Kawhi ultimately decides to sign elsewhere, all signs point to Los Angeles. The Clippers do not have a renowned medical staff. The Clippers do not have two all stars to pair with him (at least not now, and there are no guarantees they will). The Clippers do not play in the easier conference. What the Clippers do have over the Raptors is warm climate and a chance to play in his hometown. The weather doesn’t appear to be that bothersome to Kawhi, despite what others have made it out to be. Kawhi is aware of those reports and seems to be making an effort to point out how comfortable he is with the Canadian climate. Whether he’s wearing a thin jacket during a snowstorm or commenting on how nice the snow looks, I believe he’s knocked off “warm climate” as a Clipper advantage.

The hiring of Castleberry and Handy were solid and definitely checked off several “Will Kawhi like it here” checklist items. However, if we’re going to applaud the team staff, I’d start with Alex McKechnie. Wait a second. Is the 8-seed really going to advance?

SW: As much as I don’t really subscribe to the climate being a major drawback to Toronto’s allure as a destination (half the league’s teams are in cold weather cities, and guys only spend like four months a year in town once you factor in travel), this winter really sucked, man. Snow is really nice to look at! But what’s more important after that garbage February we just had are Kawhi’s opinions on ice storms. No sane person likes ice storms.

Remember when All Star Weekend was here in 2016, and it was the coldest weekend since the original Toronto Huskies were a thing? There’s no way that didn’t stick with people whose lone sojourn to the city came on that weekend. First impressions are lasting, fair or not. Kawhi’s first winter spent in Canada was wretched and slippery and hellish, even for a self-proclaimed garage-to-garage winter survivor. Driving was ass this year — ass enough to give me a bit of pause.

Hiring Castleberry and Handy after the Kawhi deal went down was another piece of the Raps’ holistic commitment to making their new superstar as comfortable as humanly possible in his new surroundings. Perhaps the warmth of friendly faces was enough to power him through the coldest, darkest days and months this winter had to offer.

I’m going with the assistants, which means we return to the poll.

“Snow is nice to look at” advances

(2) The Raptors Play in the East vs. (6) Pascal Siakam is really good now

SW: I dunno if anyone else has noticed, but Pascal Siakam is freaking amazing. He’s not-so-quietly taken a very real star turn over the month or so. His development has made thinking about a potential life without Kawhi in TO a kind of comforting exercise. The thought of pairing a Siakam who’s a year or two further along in the curve next to a Leonard who’s signed long-term? That’s terrifying for everyone but the Raptors. As is, the Clippers have no Siakams. They have max salary slots, yeah. One’s got Kawhi’s name on it if he wants it (lolol). And the other? The only thing more abundant than superstars on this summer’s open market will be teams trying to sign them; a lot of GMs are gonna get stuck offering $100 million to Khris Middleton. Toronto won’t have to gut their roster or overpay for their second guy — they’ve got him, cost-controlled no less! Kawhi could head to LA only to find himself another one of the league’s isolated stars. Siakam’s growth has given him a guaranteed alternative to that — to say nothing of the room the Raps will see open up in the summer of 2020 when Lowry, Ibaka and probably Gasol come off the books.

I know the Eastern Conference is the league’s junior circuit. But Kawhi’s good enough to go out west and make a team an instant contender with the help of a pseudo star or two. He’s already won a title out West for crying out loud. It just so happens that the simplest star partnership for Leonard is in the lesser conference, on the team for which he currently plays. If the Clippers had Siakam, they might actually be a team to fear. Siakam’s run in this tournament might go as deep as he is embedded in my heart. What are you thinking here Jay?

JR: Who am I to question someone’s heart? Before the season started, I remember telling many people that Kawhi would consider staying because he’s playing in the weaker conference. It wasn’t exactly the strongest reason and, with everything that’s happened since October, it’s not as strong a reason now. The top of the East is loaded all of a sudden.

Siakam’s improvement this season can’t be understated. He’s only been playing basketball for eight years. In 2009, he was still on his way to becoming a Catholic Priest. Now he’s a soon-to-be Most Improved Player award winner, a future All-Star, and a legitimate two-way threat that playoff teams must game plan for. Also, the chemistry that Pascal and Kawhi have built over the season is stronger than any on-court Leonard teammate, other than Danny Green.

Spicy P moves on in the bracket.

“Pascal Siakam is really good now” moves on


(1) Tim Bontemps Podcast Clip vs. (5) Nick Nurse vs. The Refs

JR: Two strong quotes going head-to-head. The Bontemps quote about Kawhi being really happy just screams, KAWHI IS STAYING. However, the quote about Nurse and “seeing the same thing you’re feeling” also screams, KAWHI IS STAYING, especially because it’s coming out of Kawhi’s mouth.

I’m rolling with the Bontemps clip because it highlights an important aspect of the Kawhi-Is-Staying phenomena. Media outside of Toronto are starting to realize that Los Angeles is no longer a foregone conclusion to be Leonard’s home next season. Sure, it’s been a fun season-long gag calling out various cues about Kawhi’s affinity to Toronto. But, up until recently, it felt like homerism for Toronto fans to think he’s staying in the Six. When a reputable NBA reporter like Tim Bontemps starts noticing, it’s kind of a big deal. Wouldn’t you agree?

SW: Yeah, as I alluded to with the Windy clip earlier in the post, I think the national reporters catching wind of Kawhi’s contentment is a pretty big thing to make note of. Hard news always starts with whispers, and Bontemps’ talking about how psyched Kawhi seemed to be about life when he saw him was the first truly audible one from outside of Toronto.

I’m not saying Nurse’s staunch, fine-earning defense of Leonard against the basketball cops isn’t a strong contender here. Coach-player bonds have some importance — just, maybe not to Leonard. If Gregg Popovich wasn’t enough to bridge the gap between the Spurs and Kawhi, then I’m not counting Nurse as one of the main draws of the Raptors as far as keeping Leonard around is concerned. Give me those juicy bits of speculation and scuttlebutt from folks in the know, baby.

“Tim Bontemps Podcast Clip” advances

(2) “Toronto has great energy” vs. (6) Masai’s Media Day Speech

SW: Can you imagine being the poor bastard across the table from Masai Ujiri in a negotiation? Saying no to him must be impossible, in no small part because of how freaking much he believes in what he is selling.

For years, Ujiri’s been reinforcing a promise — a guarantee that one day, some superstar around the league is going to realize how dope a city Toronto is in which to both live and play. His speech on Day 1 was the latest example of his trumpeting of Toronto’s quality, and probably the most emphatic.

Kawhi’s smart enough to have come to the realization that Toronto’s “energy” is truly something to behold on his own. But Masai’s felt that way about Toronto deep in his bones for years. It’s that conviction, that belief in what he’s pitching Kawhi’s way that compels me far more than Leonard’s early season statement of some frankly obvious facts about the very good city that likes basketball. Ujiri, like this new version of Siakam, is a recruiting tool on his own. And by my reckoning, he’s a damned impressive one. Masai’s speech moves on for me. Where do you stand, Jay?

JR: “The narrative of Kawhi not wanting to stay in this city is gone. I think that’s old and we should move past that. Believe in this city. Believe in yourselves. First of all, here in Toronto, we have to believe in ourselves, right? We should stop talking about Kawhi coming to this city or wanting to come to this city — that’s old talk. Kawhi wants to win. We have a privilege and an opportunity to be one of the NBA teams here. That’s a huge privilege for us. And it’s our jobs to try and bring these players. It’s our jobs to try and sell these players. But we’re proud of who we are. We’re proud of to have these guys. We’re proud to have the young players we have here. We’re proud of what Kyle and what everybody has done to help keep Kawhi here. So, let’s be proud and let’s move past that narrative of Kawhi wanting to stay here. HE. STAYING.”

That’s the unofficial transcript of Masai’s speech which also doubles as my official vote. Masai moves on in the bracket.

“Masai’s Media Day Speech” advances


(1) Serge Ibaka’s Existence vs. (4) Norm Powell & Kawhi’s Mom are Pals!

JR: What’s so great about Serge is that his web series, How Hungry Are You, has been timed perfectly all season long. The first episode with Bismack Biyombo was published the day before the Kawhi trade, so it kinda flew under the radar. It had a short life span of approximately 6 hours of Raptors Twitter gawking, perplexedly saying “he served what?!?!? cow tongue??” The Bench Mob episode really brought the series to a new level of entertainment and rewatchability. With various teammates and celebrities joining subsequent episodes, popularity for the series continued to grow. However, the underlying question in the backs of all Raptors fans minds was, “will Kawhi ever be on the show?”

After enduring a season of lamb brain, worms, and pig head, here’s hoping the season two finale is one to remember:

[Wide shot, Serge’s dining room]

Serge walks out of the kitchen with a giant platter. As he approaches him, Kawhi lets out his famous nervous laugh. Serge lifts the cover and reveals Kawhi’s new contract. *scene*

Sorry Norm. I appreciate what you’ve done but here’s where your run ends.

SW: Every favourite is better off getting a good challenge early in the tournament as opposed to going untested until the stakes are highest. That’s what Serge Ibaka is getting here. The Norm-Kim connection is clearly strong, as is the shared love for San Diego between Powell and Kawhi.

But Ibaka, man. He really does seem like the closest thing to a true pal Kawhi has found on Toronto’s roster. And it’s not just the many instances of Ibaka and Kawhi sharing a smile or a hug or an Instagram teaser video that has me convinced of Ibaka’s importance. It’s the times at which Ibaka has been the target of Leonard’s scorn after a miscue on the floor, and their ability to overcome them, still oozing adoration for one another, that have cemented my belief in Serge being the MVP on the Kawhi pursuit. It’s the kind of relationship of accountability the trash ass Celtics wish their impending free agent star was capable of having with his teammates. Kyrie has telegraphed his decision to leave with endless public jabs against the media and Boston’s youths. His departure feels like a foregone conclusion. Leonard’s been chill with the media, and able leave in-game disagreements with the likes of Ibaka on the court where they should stay. Ibaka is critical to Toronto’s friendly team dynamic; indispensable, even.

Serge Ibaka’s Existence” advances

(2) Load Management vs. (3) Raptors go all-in at the deadline

SW: It’s such a shame bracket content has to, by internet law, drop in line with the start of the Exploitation Ball Tournament. Had we been given an extra week to get it rolling, we would have had like three new one seeds to throw into the bracket.

One of those would be this quote, given by Kawhi after Friday’s game against OKC.

If you’ve been one of the people getting wet-pantsed about Kawhi regularly sitting games this year, you should have to get that tweet tattooed on your thigh.

That one word, trust — it’s the most important thing Leonard’s uttered since becoming a Raptor. Piecing together all the reporting of whatever the hell it was that happened last year in San Antonio, it’s seems trust was sorely lacking between Leonard and the Spurs. I’ve been nursing a theory all along that Kawhi always wanted away from the Spurs more than he wanted to be in LA. Maybe that’s just me rocking the rosiest coloured glasses, or maybe all Kawhi wanted was to feel heard by the medical staff tasked with keeping him healthy.

If listening ears are what he’s after, reports suggest the Raptors are providing them. Load management is just the part of the Kawhi-doctor relationships we see on the court; it must be yielding positivity behind the scenes, too, given the report Josh Lewenberg dropped on Monday. Rest his ass all he wants, man.

I’ve got load management moving on. It’s certainly not a bad thing that the Raps went all-in with the Gasol deal. But all the talent in the world wouldn’t matter if Toronto hadn’t gone all-in on Kawhi’s health as well. Whatcha thinking here, Jay?

JR: I agree. If we held out a bit longer, this bracket would have looked a lot different and with stronger high seeds. On the flip side, had we released this earlier, maybe some heavy hitters like Serge’s Existence and Tim Bontemps podcast don’t make it past a round or two. You’re damned if you do and you’re damned if you don’t.

The same can be said about the Raptors coaching staff and their Kawhi Leonard Load Management program. You’re criticized if you play him every game because health was one of Kawhi’s biggest concerns heading into the season. You’re criticized if he sits out 1 in every 4-5 games because you’ve spent your hard-earned dollars to see Kawhi play and damnit he’d better not sit for no reason.

Managing Kawhi’s workload was the ultimate 2-birds-with-1-stone approach. Appease the superstar who has had a jaded past with medical staffs, while also keeping him fresh for the playoffs. The fact that Toronto, despite losing bench depth, was able to reel off 15 wins in 20 games without Kawhi certainly helped.

Masai and Bobby working some deadline magic is absolutely a worthy foe, and certainly sends the right message to Kawhi that they’re willing to win now. But the risk of shipping away Jonas Valanciunas, Delon Wright, and CJ Miles (DeMar DeRozan and Jakob Poeltl qualify here too) for a one-year run at the title (hypothetically) still not as big of a risk as it would have been to take Leonard’s health concerns lightly.

“Load management” advances

Here’s a look at the updated bracket:

Come back on Friday as we move into the quarter-finals!