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Was the Kawhi Leonard trade actually a risk for the Raptors? A debate

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Did Masai Ujiri really make a bold gamble trading for Leonard, or was it actually riskier to keep the status quo?

Last July, the Toronto Raptors traded for Kawhi Leonard. By itself, with no other context in the frame, that sentence should be viewed as a humongous victory for that organization.

But Leonard was not coming off an MVP-caliber campaign when the Raptors acquired him. A mysterious quad injury effectively ended his 2017-18 season with only nine games under his belt — in eight of those nine, he did not crack 30 minutes. On top of that, 2019 would be the final year of his contract, meaning the Raptors might have just forked over DeMar DeRozan, Jakob Poeltl, and a first-round pick for one year of Leonard, if healthy. (Also, Danny Green, which is important to note).

That sounds like a risky move, but was it? Looking back on the deal one week after the Raptors won their first championship in franchise history, SB Nation’s Mike Prada and Michael Pina debate that question below.

MIKE PRADA: All season long, Masai Ujiri’s decision to trade for Kawhi Leonard has been classified as a gamble. “Will Kawhi Leonard validate the Raptors’ big bet” is the exact language I used in tracking the impact the playoffs will have on the NBA’s biggest stories. It seemed obvious to me that trading for an injured star with no assurances he’d stay beyond this season was a big risk. I didn’t even think to call it something else.

But you don’t see it that way. Is it fair to say you don’t think it was a risky move at all?

MICHAEL PINA: For a variety of reasons, I don’t.

Some of why I feel the way I have isn’t based on rational thought. I recognized Kawhi’s injury history but, him being someone I long thought would unseat LeBron James as the proverbial Best Player Alive, even 90 percent of that talent was far better than DeMar DeRozan, Jakob Poeltl, and a late first-round pick. So I never expected him to be anything less than great this season — a contract year in which he’s trying to get paid. By the time meaningful games roll around, he’d be in good enough shape to rediscover his apex.

Now, even if the real “risk” here centers more around Leonard’s free agency than his health, to me, as an organization that’s long operated with an NBA championship in mind, another season of Kyle Lowry and DeRozan would be a far worse gamble.

During his introductory press conference back in 2013, Ujiri told media members assembled before him “the overall goal in the NBA is to win a championship. That has to be the overall goal. It’s not playoffs, it’s not … it’s to win a championship at the end.”

Fast forward to last summer. The Raptors had won 48, 49, 56, 51, and 59 games with Ujiri at the helm, and had zero appearances in the Finals to show for it. Two roads are then presented:

  1. Trade for Leonard (and Danny Green) without surrendering your top two assets, then, even if only for one year, dramatically raise your organization’s ceiling, or ...
  2. Run it back and, in all likelihood, lose in the first, second, or third round. Again. With DeRozan about to turn 30 on the final year of his contract. Lowry is 33.

Which option is a greater risk?

PRADA: First of all, you can’t just hand-waive the injury risk away. Kawhi spent the entire season battling a medical staff purported to be among the most forward-thinking and player-friendly in the entire league. He played nine games during the season and shut himself down in the middle of that process. No matter how great a fully healthy Leonard is, you’d be nuts to not worry about the possibility of re-injury or, worse, permanent decline. (Regarding your point about him wanting to prove himself in a contract year and thus get himself in better shape, we just saw Kevin Durant and Klay Thompson show that will alone cannot overcome the realities of the human body).

Second of all, the choices you present are vastly oversimplified. It’s not like Ujiri was spoon-fed that final offer and simply had to accept it. He had to do the work to seek it out, negotiate the Spurs down, divert attention away from other potential transactions, and ultimately complete it, all without jeopardizing the mood of the roster if it fell through. To go through all that, you have to make a decision that what you have isn’t enough and that the best way to get out is to stake everything on one season with a player that may not be healthy.

Remember, Ujiri didn’t exactly break up a 40-something-win low-playoff seed. He broke up a team that won a franchise-record 59 games, led by the coach of the year and two stars who finally embraced a city that had been spat on throughout its history. He sacrificed a homegrown talent for a one-year chance to improve on the best season in franchise history. It’s easy to say the DeRozan-Lowry Raptors hit a glass ceiling, and maybe they did. But with LeBron James out of the conference, there was reason to believe the team who had the best record in the conference the season before could step into the power vacuum without doing anything.

Given all those conditions, Ujiri vigorously pursued and executed the trades. I buy that it was smart. I don’t buy that it had no risk.

Here’s a question for you: if exchanging that level of a trade package for one guaranteed year of Leonard was such a low-risk move, why didn’t any other team beat the offer? Why is the idea of trading for a “rental” still taboo to so many?

PINA: I do not dispute that trading for a one-year rental is typically a gamble, but the particulars that apply to Leonard and Toronto do not translate across the board. The Raptors were simultaneously on the doorstep of a Finals appearance—sans enough talent to actually make it—and on the verge of starting over. How many teams can say that?

This trade was a way to get in front of the inevitable, upping championship odds without mortgaging the future. How much worse is their long-term position if Leonard’s leg falls off a day after he lands in Canada, really? Before the trade, this team was running in place; a rebuild was on the horizon. Kyle Lowry and Serge Ibaka were not offered the five-year deals they wanted in 2017, and Ujiri reportedly offered DeRozan to the Thunder for the same package (Victor Oladipo and Domatas Sabonis) they traded for Paul George.

With Kawhi, a rare opportunity presented itself and Ujiri snatched it without having to fork over anything of real substance (outside a late first-round pick) that would be useful after DeRozan and Lowry’s contracts expired.

The Raptors only had so long to break through, and even without LeBron in their path, let’s please be serious about how good this team would’ve been with DeRozan as a first option this season. That squad is more likely to fall against the Magic than defeat the 76ers. We know they weren’t good enough to fill any LeBron-less vacuum, either. Since Ujiri was hired, Toronto’s postseason plus/minus was -11, -56, -85, -57, and -44. They were outscored by 10 points against the Indiana Pacers in 2016, and scored just four more points than the Milwaukee Bucks in a six-game series the following year.

Meanwhile, every other realistic suitor either had no urgent motivation to shake things up (Boston and Philadelphia), or figured they could just sign him in free agency (both teams in LA). Trading for Leonard was an unnecessary and legitimate risk for them all because, at the time, Boston and Philadelphia was confident in their future. Dealing attractive assets that doubled as present-day contributors could’ve ruined that if Leonard walked. These teams were young, with key pieces that had untapped potential, and their front offices had reason to believe internal growth could guide them to a championship. The Lakers and Clippers were incentivized to pursue Leonard in free agency. Why give anything up when you can get him for free?

The Raptors had none of that going for them. If they keep Leonard, great. If not, they are where they would’ve been anyway, set to enter a different part of their franchise life cycle. For them, standing still was always the greater risk.

PRADA: All that is fair, and I get that Toronto’s situation was somewhat unique.

But to me, that actually underscores why this trade was risky. The assumption in all your detailed analysis of the situation is that any NBA team would process their situation the same way Ujiri and Toronto did, and that’s simply not an assumption I’m willing to make or take for granted.

Forget the teams you mentioned, even though all of them took a safe route that the Raptors could have justified. Where were other “stuck” teams in the Leonard trade picture? Where was Portland, for example, another team built around two guards that didn’t have a clear path to contention? Where was Washington? Where was Indiana? Where was Miami? Where were any number of teams that had a DeRozan-level player and weren’t coming off 59-win seasons with multiple all-stars on the best team in franchise history? Nitpick the particulars of each all you want, but if trading for Leonard wasn’t a risk, then it follows that all or even just one those teams would have at least jumped in more aggressively and forced Toronto to come with a better offer.

Actually, here’s a better comparison: the mid-10s Clippers. Both teams achieved historic success for their morbid franchises, yet kept bumping up against glass ceilings in heartbreaking fashion. Both teams had decisions to make: play it “safe” and try to nibble around the edges, or go for broke and make dramatic changes to their cores.

Were the Leonard trade not a risk, these two teams would have both chosen Option No. 2. Instead, the Clippers kept trying to run it back, while the Raptors bullied their way into the Leonard sweepstakes and got the deal done.

Ultimately, I think our disagreement stems from the idea that the Leonard trade, in your words, was “a rare opportunity that presented itself.” My point throughout is that opportunities don’t just present themselves to you. You have to make a bet against incumbency bias to go get those opportunities with as much zeal necessary to get deals done. That’s where Ujiri really made his bold gamble.

PINA: See, I don’t think there was any other team that can be compared to Toronto. Bradley Beal and Victor Oladipo are four and three years younger than DeRozan, respectively, and the Heat had nothing close to a perennial all-star on their roster. The Raptors were coming off a season in which they had the best bench in basketball. They were built to go from DeRozan to Kawhi and expect a championship, knowing Lowry, Ibaka, Siakam, OG Anunoby, Fred VanVleet, etc. were there as a solid support system. There were even more paths to upgrade the roster (Jonas Valanciunas, Delon Wright, and CJ Miles for Marc Gasol), too.

In other words, the Raptors were unique.

I don’t think they shared much beyond postseason disappointment with those Clippers, either. Those teams were good, particularly when Chris Paul first got there. From 2013 to 2015 they finished with a top-three point differential, which is obviously plenty good enough to win it all, and when healthy their stars were even better in the playoffs than they were during the regular season. The same can’t be said for DeRozan and Lowry.

At the end of the day I fundamentally don’t believe trading for Leonard was a risk in Toronto because A) they didn’t give up much, and B) they were headed towards a notable step back from anything close to title contention if they did nothing at all. For Toronto, it was always worth it to make this deal. Even if it blew up in their face, they wouldn’t be in any worse position than had they done nothing at all. Risk implies they had something to lose, but by doing it, all they had was a championship to gain.