The Raptors won an NBA title. Now it’s time for two

As the confetti came streaming down and a group of die-hard Raptors fans chanted and sung at Oracle Arena, the TV began to cut to the seemingly never-ending series of Jurassic Parks scattered around Canada (59 in total plus Rockford!).

In each locale, hundreds, or thousands, or sometimes tens-of-thousands of Raptor fans had gathered to support the nation’s basketball team, and they were losing their collective shit.

It was an awesome moment. I’m not embarrassed to say it brought a tear to my eye to think of how many people were feeling the sort of screaming catharsis that really is reserved for winning championships, or wars.

In the middle of this I got a text from my childhood friend Gerald. Gerald and I had been playing hoops on his slanted driveway since Grade 6. He was a die-hard Bulls fan, I loved the Pacers. We once organized a two-on-two league at our school, complete with logos, stats and standings. Simply put, we’ve been hoops junkies since a time where the hockey crowd called that treason. [Editors Note: Conor also loves hockey. He’s just not very good at it. Or basketball for that matter.]

“How can Kawhi leave this?” Gerald’s text said.

More than ever that’s a valid question. Let’s look at a few of the key issues that might inform the answer.

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The Raptors should be really good again next season

The first thing to know about the Raptors for next season is that Toronto can pretty easily bring back the entire championship team.

Kyle Lowry, Serge Ibaka, Pascal Siakam, Fred VanVleet, Norm Powell, and OG Anunoby are all under contract for next year.

Marc Gasol has a player option, and it’s possible he could opt out — especially if Kawhi doesn’t stay — but it’s for a hair under $26 million, and as good as the Spanish veteran is, ain’t nobody paying Marc Gasol $26 million next year.

Danny Green is a free agent, but the Raptors have his Bird Rights — which basically means they can go over the salary cap to resign him. Green made $10 million last year. It’s hard to handicap what he might get on the open market, but signing him for two plus an option makes sense — as even if Masai Ujiri wanted to pivot, a 3-and-D veteran like Danny Green is exactly the kind of pick-up championship-calibre teams want to add at the deadline.

Basically it’s just the Raps spending money. An easy thing to say since: a) it’s not mine, and b) keeping this core will vault the Raptors deep into the luxury tax again, but, my four years of business school says: deep playoff run + giant TV ratings + a ton of merchandise sold = solid financial decision.

Kawhi is legitimately about winning

Kawhi’s been famously upfront about this whole process, all his comments basically boil down to: “you know what you want, but you don’t think about it until the job is done.”

Well, the job is done now and you could argue that a title adds weight to both the “stay” and “leave” sides of the scale. A title means mission accomplished for Kawhi. He can leave for L.A. knowing that he will Ka’wine and Dine in Toronto for the rest of his life regardless.

The title, and the ability to bring back the core also means Kawhi can do something he’s never done before — win back-to-back titles, which, post-Jordan would put him in the rarefied air of stars like LeBron, Kobe, Pau, Shaq, and the Golden State crew.

Kawhi has said nothing matters to him but winning. Winning and becoming a legend. He’s already just one of three players to win Finals MVP awards on two different teams. Winning a pair of titles as the King of the North would never be forgotten in this country, and it would cement his claim as “best player in the world.”

He’s left a lot of money on the table

There’s also the matter of the money.

Kawhi potentially gave up a $219 million “supermax” contract extension when he forced his way out of San Antonio. (I say potentially, because it’s possible the Spurs may have balked at giving Kawhi that contract given his injury woes. Unlikely, but possible.)

The Raptors can offer Kawhi a five-year $190 million contract if he chooses to stay. The most any other team could offer is $141 million.

So, he’s already given up almost $30 million. Would Leonard REALLY leave another $50 million on the table?

Again, there is an argument for both sides. Kawhi has shown that what he wants is worth giving up a significant amount of money once before. Then again, we’re talking almost EIGHTY-FREAKING-MILLION DOLLARS!!!!

This is somewhat rendered moot by the fact that Kawhi could ask the Raptors to engage in a sign and trade. The Raps would ink Kawhi to the bigger deal, his team of choice would give up some assets (likely assets they’d need to trade anyway to clear space for the bigger contract), and Leonard would end up where he wants.

In this scenario everyone, mostly, wins. Kawhi gets paid and gets where he wants. The Raps get some assets and build on their rep on being a player-friendly organization, and the new team... let’s say “the L. Clippers” (no, wait, that’s too obvious — let’s say “the LA C’s”), gets arguably the best player in basketball.

That obviously isn’t the best scenario for the Raptors, but it shows that the money edge isn’t as big as it might seem for the hometown boys.

So what’s going to happen?

When the trade went down last year, I believed that the Raps had a better chance to resign Kawhi than the (mostly American) talking heads believed, but I wasn’t, you know, confident.

In the past few days, though, a pair of reports have got me very optimistic (no, this has nothing to do with Kawhi allegedly buying property in the Six — but damn, I’ll house-sit on one of those West Coast jaunts).

One was about Kawhi Leonard — with a few places reporting he was interested in a short term deal with the team. The other was from The Atheltic’s Frank Isola saying the Warriors had planned to offer, pre-injury, Kevin Durant a long-term deal with an “understanding” that they’d move Durant if he ever wanted to go.

Both of those would make sense. In one, Kawhi can sign for two years. This works for a host of reasons, including the fact that in two years free-agent Kawhi will be eligible for the largest of the “supermax” extensions, and that a two-year deal lines up pretty well with the Raptors current window. (Sportsnet’s Steven Loung wrote a good piece explaining this all in more detail.)

The Durant one is interesting to me as well, though. Kawhi does have injury concerns. Two years, with a player option at the end would give him protection in case he gets hurt again, but you know what’s even greater protection? A five-year deal with a Player Option at the end.

A deal like that means Kawhi could hit free agency as early as his year 31 season — setting him up for another massive payday, while giving him a $190 million security blanket for now. And “the understanding” would give Kawhi a ton of control over his career. Lowry, Gasol and Ibaka all walk after next year? So can Kawhi. Siakam doesn’t develop any further? Kawhi can find a partner who is. The winter is just too damn cold? Head for the beach, Klaw.

Of course, the Raptors and Kawhi “understanding” would only be a handshake deal. Kawhi would be putting a lot of trust into the Raptors organization. What if Masai Ujiri leaves? Or relationships fray?

Then again, as we’ve seen over and over, all contracts with superstar players are handshake deals. The very best players have so much leverage that the term of a deal means nothing. If Anthony Davis wants out, he says he wants out, and the Pels are going to move him. Kawhi himself was one of these examples.

I’m fine with that. Players should use all the leverage they can, because as we saw, sadly, twice in this series, devastating injuries can happen at any time.

Regardless, the short term deal, or the long-term understanding both make a lot of sense. Kawhi can maximize short-term earnings, set himself up for a bigger long-term payday, stay with a city and organization that has done right by him, and, more importantly, has the tools to win again.

When the free agency bell rings on June 30, anything can happen, but more and more, you have to think that with the right contract offer Kawhi will also wonder “how can I leave this?”