Adon Moss
9 min readApr 3, 2019

What Are The Toronto Raptors Going To Do This Offseason?

We’re in the listless days of the NBA season, where teams are gearing up for the Golden State Bowl or winding down for the Zion raffle. Most are more or less locked into their seedings, rendering the majority of the remaining games lackluster. Which means that for ten more days we get to engage in the it’s-way-too-early-to-talk-about-the-offseason-but-we’re-doing-it-anyway discussion.

For the Toronto Raptors, the shadow of July 1st has loomed for months. Within that nebula, lays the answer to the future of the greatest player to dawn a Dino. Kawhi Leonard’s To Re-sign or Not To Re-sign has haunted each and every Raptors fan since the day he was ignominiously discharged from General Popovich’s corps. What he chooses, and what happens subsequently, is the greatest Canadian “what if” since Matt Bonner’s The De-citiz-ion.

Thus far, by preserving their precious Los Angelian basketball superhuman (22 DNPs-load management and counting) for the postseason, the Raptors are demonstrating to Kawhi that we Canadians care — unlike the disciplinarians of San Antonio or the superstar-betraying Los Angeles Clippers. And that his health, now, and for the next super-max five years (!) would be the Raptors’ utmost concern.

If resting Kawhi has been a surreptitious ploy to woo him and, I think it is, then, despite this being the Raptors’ best chance at an Eastern Conference championship to date, fans and the organization are possibly more anxious about July than these playoffs.

I can just envision the cadre of sleep-deprived Raptor executives huddled up in a Freshii-container-pizza-box strewn boardroom pacing about like a group of paranoia-stricken war generals, poring over an elaborate clue wall, outlining every possible scenario for this coming summer.

But no matter what happens with Kawhi’s Shakespearean dilemma, there are a myriad of uncertainties with permutations to follow: what to do with the old guard, how to nurture the youthful vanguard, and who to sign in free agency.

So let’s take a look at some of the ways that it could go.

Running it back — with Kawhi

Truly, how does Kawhi not stay in Toronto?

For that matter, how is every agent of a decent NBA player not telling their client to flee for the unclaimed territory of the Eastern conference where a litany of bounties await: sub-five hundred records making the playoffs, All-Star appearances-a-plenty (debates like Jimmy Butler v Nikola Vucevic should not be happening while more deserved players tearfully accept that the Western Conference is stacked), and a much less competitive night-to-night schedule?

Ok, Giannis is probably the reincarnate of Lebron. And Philly has something cooking. And New York miggghhhttt end up with these two impassioned? sensitive? whiny? superstars and Zion Williamson. And, yes, Boston and Indiana are threats, but the Celtics’ franchise is in more disarray (and bear more animosity towards one another) than House Lannister, and the Pacers have to wait on Oladipo’s health and address a number of offseason decisions first.

Compare that to the army of Sauron standing in the West, and Kawhi — unless he hates the cold that much — has to stay in Toronto, right?

Oh, and did I mention that an injury-plagued 27-year-old can sign for $190 million over five years with Toronto, but only $141 million for four years anywhere else?

So let’s say he does stay — it would be the savviest free agency play since the Clippers liberated Deandre Jordan and broke The Marc Cuban Siege of 2015.

Then what?

If this year’s chase fails — failure being anything short of a Golden State Warrior drubbing — do they run it back?

The Raptors mantra of the past has been to do just that: a tweak here, a tweak there, stay the course.

That would make sense. Running it back. The Raptors are a dangerous team with Kawhi and company. They could bring back Danny Green, have another year of Bench Mob development, turn the Siakam spin cycle to high, make a sneaky veteran signing, and go for it again. A crew of overpaid, battle-tested veterans, spicy young’uns, and The Klaw is a formidable NBA team.

Come 2020 Kyle Lowry, Marc Gasol, Serge Ibaka, Fred Van Vleet, and Pascal Siakam (as if they don’t resign him) are all off the books, giving the Raptors the luxury (roughly $90 million) to lure another superstar to play alongside Kawhi and company.

Retooling on the fly — with Kawhi

If Kawhi stays, IF KAWHI STAYS [insert prayer emoji], the “rebuild” is on.

Presumably, the Lowry-Ibaka-Green-Siakam & Kawhi offense(s) didn’t take. Nick Nurse’s attempt to run two separate systems at the same time went as smoothly as the invention of flubber. So we move on, but how?

Masai Ujuri’s great mastery of winning games and developing players simultaneously is evident both in the team’s ongoing record and its roster. The Raptors are gentrifying: evolving through a convergence of young and old, balanced with experience and exuberance, fuelled by grit and athleticism. It is likely Masai will stick with that patient approach — razing the old, fostering the new — through the following steps:

Unload one or both of Kyle Lowry (final year $33.3 million) and Marc Gasol (player option $25.6 million)

Not an easy task, but doable. Some would have said the Demar Derozan contract was unmovable and we all know how that went down.

Lowry and Gasol will be on the final years of their contract and still valuable veterans. Expiring contracts are attractive trading chips, enabling teams to offload cumbersome signings that misalign with their future plans. In these two’s cases, the Raptors could wait a year for them to come off the books, but rebranding the Raptors as “Kawhi’s Team” could be the impetus to start anew. Teams desperate to acquire expiring contracts are Masai’s tastiest prey.

Gasol has a player option for his last year and could opt for long-term security. In this scenario, the Raptors let him walk. If he opts in, a team like Portland who just lost Jusuf Nurkic to a horrid break of his leg could use Gasol’s services as a gap-stop. CJ McCollum’s contract matches nicely and so does his offensive prowess. There is not much else out there for slow, older centres, but a team making a push like the Raptors are doing currently could look to Gasol for depth and leadership. Charlotte, Dallas, New York, Miami, and the Los Angeles Lakers will be eyeing the playoffs next year and have contracts and young pieces to orchestrate a trade.

Lowry’s skill set and leadership are perfect for a team gearing up for a run. Particularly if that team lacks shooting and depth like Philadelphia, Detroit, Utah, Indiana, Minnesota, Orlando, and Miami. P.S. Don’t tell me Phoenix wouldn’t pull the trigger at the right price point. Each would have to give something up in return, but an expiring, a serviceable roleplayer, and a draft pick is exactly the kind of price Masai likes to fetch (a la 2015 Greivis Vasquez trade).

Keep Serge Ibaka (final year $23.3 million) and Norman Powell (two years $10.9 and $11.6 million)

Serge has become the most lovable Raptor since Junkyard Dog, and has done so while providing the team with a mean streak, a mafuzzy chef, and this era’s ideal centre: mobile, rangy, and defensively-minded. He has also cozied himself up to Kawhi, in a genuine, big brother way, that should be attributed to one of Kawhi’s reasons for staying. On that note, can’t trade Norm either.

Find the next piece(s)

Here comes the tricky part. Okay, easier said than done, eschewing Lowry and Gasol, but the algorithms suggest that Masai will continue to spin recycled sneakers into gold. If Marc Gasol opts out, he, along with Danny Green, Patrick Mccaw, and Jeremy Lin leave the team with a little bit of over $39 million to play with, minus the extra paid to Kawhi. If Gasol opts in, Lowry and/or Gasol must be part of a sign and trade. So let’s assume that one of those two scenarios unfolds.

If the Raptors are on a win-now path and fear they cannot reel in big free agents, they may be willing to take on pre-paid players (like Kawhi before) and forego future financial flexibility. It is true, Masai usually bides his time like the wizened, calculated, wizard that he is, trusting his organization and savoring his moment to act. But he also…

ALAKAZAM traded an insatiable Rudy Gay for an armada of role players and ABRACADABRA turned a washed Andrea Bargnani into a bouquet of draft picks.

He is not afraid to drop a Woj bomb from another stratosphere.

SHAZAM! Masai pulls off a blockbuster by trading Lowry/Gasol, OG, a first, and Norman Powell (he’s not entirely untradeable) for Kemba Walker on a five-year max sign and trade? Or same, same with Bradley Beal?

Add Siakam in the mix and maybe Anthony Davis leaves the Bayou for the Big Smoke? I can dream. But Brandon Ingram and Jayson Tatum have never looked less appealing. New Orleans gets a perfect guard to set up alongside Jrue Holiday and two up-and-coming-studs to build on for the future; as Bill Simmons tends to propose to the ether: who says no? If AD gets antsy, or cold, in Toronto, then the Raptors can turn around and flip him for an equal price. I digress.

In all likelihood, superstar free agency is preordained. And I can’t really talk myself into Jimmy Butler being a suitable max contract addition, nor can I imagine Kris Middleton or Tobias Harris wanting to vacate their promising futures. So, perhaps it is one sub-major signing like Bojan Bogdanovic for 4 years $100 million and resigning Danny Green or finding a Trevor Ariza for 2 years $16 million.

Less exciting, I know.

Otherwise, holding pattern is best. Smaller signings may buttress the roster, but they won’t tip the scales enough to warrant losing flexibility in 2020. Besides we’ve all seen where signing “tough veterans” gets you.

Patience is Masai’s greatest virtue. He is proven to be at his best when other teams are squeamish and disharmonious.

Life without Kawhi

Worst case…and likeliest scenario.

But, goshdarnit, it was worth it. I think I would have put my fandom on sleep mode if I had to listen to Leo Rautins massage the upside out of watching another Lowry-Derozan-Ibaka-JV season flame out in the playoffs.

Besides, I am not sure how tradeable Demar Derozan’s contract would have been if the Raptors had waited any longer. There are few teams that practice the stubbornly old-school, slow, yet successful, 2-pointers-rule-the-day style like the San Antonio Spurs.

Look, the Raptors without Kawhi are still a top 5–7 Eastern conference team even if they try and blow it up. With Pascal Siakam as a bonafide scorer, Freddy Van Vleet taking over at point, and the it’s-there-but-just-isn’t-there-yet potential of OG Anunoby, Masai can continue to cautious-aggressively build while stealing away wins.

That can look one of two ways:

Make One Last Run

Sell tickets. Sign Jeff Green and Terrence Ross. Bring in Mo-Pete as their new G-League coach. Grind out another Lowry-bum-led season. Have an Ibaka bobblehead night. Re-sign Pascal. Trade Powell for anything. Host a tribute night to Lowry and Derozan on the Spurs’ rodeo trip. Beat Orlando in the first round. Lose to the Bucks in the 2nd round. And start anew with a young, rising set of stars.

Look to the Future

Market the rebuild approach as the “Re-Drake”. Have an entire album dedicated to it. Including:

  • A cover of Old Dirty Bastard’s Back That Ass Up ft. Lil Wayne honoring Kyle Lowry’s charge-taking;
  • A diss track titled, “I got Hall-Marquese Chriss-ues”
  • An “iBLAKA ballad”;
  • An interlude with Jamal Magloire talking to his tailor about his custom-made suits; and
  • A dancehall, reggaeton track titled “Spicy P.”

Trade Lowry and Ibaka at the deadline to playoff contenders. Re-sign Pascal. Trade Powell for anything. Miss the playoffs, or, who are we kidding it is the Eastern Conference, lose to New York in the first round. And launch into 2020 with a young and financially flexible team.

There really is no worst-case scenario for the Toronto Raptors. A tribute to the organization’s ability to draft, develop, and trade players successfully. Unfortunately, functioning as a mid-market team demands it of them. Toronto is not top-of-mind to any superstar, and may never be. The Raptors do not have the luxury of making Hideo Turkoglu-ean sized errors, but they do have the acumen to make Kawhi Leonard and Marc Gasol-type risks. Either way, the Raptors have to be methodical and thoughtful as they face the unenviable challenge of trying to win now while continuing to act for the future.

Adon Moss

Policy Analyst; Strategic Foresight Analyst; Freelance writer; Basketball Opinionist.