Toronto Maple Leafs: Lessons From Masai, Part Two

TORONTO, ON - MAY 12: Philadelphia 76ers center Joel Embiid (21) watches from the corner as Toronto Raptors forward Kawhi Leonard (2) squats down and sticks out his tongue waiting for the ball to drop for Raptors to win. Toronto Raptors guard Jordan Loyd (8) (in cities) starts the celebration. Toronto Raptors vs Philadelphia 76ers in2nd half action of Round 2, Game 7 of NBA playoff play at Scotiabank Arena. . Toronto Star/Rick Madonik (Rick Madonik/Toronto Star via Getty Images)
TORONTO, ON - MAY 12: Philadelphia 76ers center Joel Embiid (21) watches from the corner as Toronto Raptors forward Kawhi Leonard (2) squats down and sticks out his tongue waiting for the ball to drop for Raptors to win. Toronto Raptors guard Jordan Loyd (8) (in cities) starts the celebration. Toronto Raptors vs Philadelphia 76ers in2nd half action of Round 2, Game 7 of NBA playoff play at Scotiabank Arena. . Toronto Star/Rick Madonik (Rick Madonik/Toronto Star via Getty Images) /

The Toronto Maple Leafs and Toronto Raptors share more than just a building.

Ten months ago, mere days after the Toronto Raptors officially shipped out the most beloved player in franchise history, DeMar DeRozan, I wrote about the lessons such a cold, calculated, yet essential move could teach the Maple Leafs. There were many.

Trading DeRozan was an unthinkable act to a large portion of the Raptors fanbase at the time.

Who cares about the return? To them, DeRozan was Toronto – a player who, at his core, exuded the city’s very essence; both viciously proud and deeply insecure. A star, but not a superstar. Good, but not good enough.

For better or for worse, fans saw themselves in DeRozan. He gave them something to unite around, a beacon in a decidedly dark landscape. And at a time when the NBA thought of Toronto as basketball purgatory, DeRozan affirmed his commitment by re-signing with them in 2016, all while the possibility of joining his hometown Lakers loomed throughout.

DeRozan gave Toronto the loyalty it had yearned for all along. All Toronto wanted to do was give it back.

Alas, NBA titles are not earned from loyalty. They are earned from winning. And on the heels of a half decade’s worth of repeated failure to do so when it mattered the most, Masai Ujiri sat a crossroads.

His options were simple: Either double down on this being the year that Sisyphus pushes his rock up the hill, and therefore risk watching it all tumble down once again, or, simply, find another route.

It’s the type of decision any sports executive dreads the most.

Swapping DeRozan out for the clearly-superior Kawhi Leonard made sense from a basketball perspective, without question. Leonard was and still is an elite talent of franchise-altering proportions, thought to be the one player capable of shutting down Toronto’s everpresent boogeyman, LeBron James. (remember when everyone thought the Lakers would be good?) There’s no debating that. It’s a fact.

But Leonard’s commitment to Toronto and, therefore, his loyalty, was anything but.

Even so, Masai did not care. He couldn’t. And in perhaps the riskiest move in Toronto sports history, Ujiri chose to jettison a franchise icon for what was, at the time, nothing but an increased shot at a title. A shot which, even today, could very well confine itself to a one-year window.

Maybe the Raptors make this move and get their superstar, only to again fall short of championship glory and find themselves right back where they started, this time with nothing to show for it. That’s a risk Ujiri was all too willing to make. For if he didn’t, and Sisyphus failed once more, the regret of choosing comfort over what could have been would be too awful to bear.

So, Masai went all in.


Back in July, I noted that Kyle Dubas would one day find himself at a similar crossroads. I just never thought he would reach it so soon.

Having just watched the Maple Leafs’ season end in heartbreaking fashion at the hands of their most hated rival for a second consecutive year, Dubas now enters into an offseason not unlike the Raptors’ from 2018. Seismic changes are supposedly coming to a roster that, despite his best mid-season efforts, failed to get over the hump.

Dubas instead could opt for comfort, of course, just as Masai pondered those then months ago.

The salary constraints which Toronto will grapple with this summer could very well convince the 32-year-old to re-assemble the troops for another kick at the can, albeit with even less wiggle room than before. After all, the 2018-19 Maple Leafs were a good hockey team. They wouldn’t have pushed the Cup-favourite Bruins to the brink of a Game Seven if they weren’t.

But they failed. And that failure, even after its sting began to fade, only reaffirmed to fans, and Dubas, what each party had known all along: those Maple Leafs were good, but they weren’t good enough.


Kawhi’s historic, series-winning buzzer beater in the dying seconds of Sunday’s Game Seven to push the Raptors to the Eastern Conference Final does not validate Masai’s gamble on its own. There is still much left at stake.

What it does instead, though, is bring that gamble one giant step closer to validation.

The Raptors don’t win that game, or even push Philadelphia as far as they did, with DeRozan still on their roster. That’s not a criticism on DeRozan, who is undoubtedly a fine player himself. Rather, it’s merely a testament to how jaw-droppingly absurd Kawhi’s shot truly was. Only he could have made something like that, and, as if by fate, the ball landed in his hands.

This is exactly why Masai took a risk this past July. In going after Leonard, Ujiri did whatever it took to give his team a superstar solely because he knew, in the sport’s biggest moments, only superstars can trigger the impossible.

On Sunday, that’s exactly what Kawhi did.

Dubas just so happens to share a building with the guy who got him.


Regardless of what ultimately transpires over the summer, the Maple Leafs are due to find themselves in a similar make-or-break situation next season, just as they have in the previous two. It’s inevitable; one part fate, one part side effect of the NHL’s broken playoff format.

But unlike the Raptors, Dubas already has the superstars of which those moments demand. Auston Matthews and John Tavares are locked in together for the foreseeable future. Their loyalty is defined.

Where Dubas’s crossroads lie now, rather, is at the bodies surrounding them.

If you’ll recall, DeRozan was far from the only casualty of Masai’s go-for-it exorcism. Jonas Valanciunas, Delon Wright, and C.J. Miles – all valued role players – were dealt to Memphis at the trade deadline in exchange for a superior asset in Marc Gasol.

All three former Raptors are respected role players in their own right; former two serving as important members of Toronto’s vaunted “Bench Mob” back in 2018. But Gasol brings something different. His arrival endows upon the Raptors a commodity, much like Leonard’s did, that neither Valanciunus, Wright, or Miles could provide.

Once again, this team does not move on without Gasol, whose lockdown defensive coverage effectively neutralized Joel Embiid for most of the series. It was gut-wrenching to usher that trio of beloved and long-standing players out, but it was Ujiri’s calculated decision-making that ultimately birthed tangible results.

The onus now falls on Dubas to make some gut-wrenching moves of his own to do the same.

It’s no secret that Toronto’s young players love Patrick Marleau enough to consider him a pseudo-father. His roots within the dressing room run deep. And yet, if Marleau’s presence on the roster is withholding it from success – which appears to be the case now given his current state – Dubas must find a way to rid himself of a man whose commitment to the Maple Leafs is so strong, he moved his young family half-way across the continent as a result.

That conversation won’t be easy. DeRozan’s wasn’t either.

However, if Dubas deems it necessary, then it must be done.

Selling Connor Brown – who joined the Leafs in 2012 as a sixth-round pick before working his way into the NHL and then took what, at the time, appeared to be a discount on his first contract –  is another possibility. As is cutting bait on Nikita Zaitsev, who uprooted his life from Russia to Toronto and is now just two years into a seven-year extension. Or perhaps this means turning Nazem Kadri – a member of the organization since 2009 – into that sorely-needed right-shot defenceman.

Those are just a few particular avenues Dubas could saunter down. Make no mistake, there are numerous others, each requiring its own difficult conversation. Bad blood will result. As Mike Babcock famously said four years ago, there will be pain.

When the great people of Toronto woke up Monday morning, however, my guess is that the pain of DeRozan’s dismissal failed to cross anyone’s mind. Winning tends to do that, after all.

Ten months ago, Masai Ujiri took the biggest leap possible on the mere hope, slim as it may have been, that it would make a positive difference. And ten months later, that’s exactly what it did.

Now on the precipice of his own legacy-defining offseason, Dubas must decide whether to take a lesson out of Ujiri’s book and jump, knowing full well of what risks could await.

Next. Lessons From Masai. dark

Thanks for reading!