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On Masai Ujiri’s big move and loyalty in professional sports

The Raptors boss is catching flak for his treatment of a homegrown star. Is it deserved?

NBA: Toronto Raptors-Media Day John E. Sokolowski-USA TODAY Sports

The Kawhi Leonard era is underway in Toronto, and its opening (and perhaps only) season represents a significant fork-in-the-road for the franchise. The window for contention, pegged at three years before last season began, has possibly been reduced by one — that is to say, it’s this year or bust.

If Leonard is healthy and engaged, however, that one year of opportunity has a far greater chance of success than any iteration of the Raptors to date, We the North era or otherwise.

If this year fails (or even if it doesn’t, potentially), an eventual rebuild leers like a catcalling drunk, turned out of the bar before midnight — they have no place to be, but also no place to go, so you’ll just try to live your life without acknowledging their presence any more than is strictly necessary, until they push the envelope or disappear into the night.

With questions swirling around Leonard, and romantic laments for DeMar DeRozan overloading your Twitter-feed, it’s difficult to know exactly how to feel.

Does sadness at DeRozan’s departure outweigh all? Should we be angry at how he says he was treated? Or simply ecstatic about the Raptors landing a superstar, costs be damned? How about feeling wary that said superstar seems to perpetuate all the nightmares chip-on-their-shoulder Toronto sports fans have when they shut their eyes?

It’s likely an emotional smoothie made up of all of these things. For now, the questions about Kawhi, at least, are unanswerable.

So let’s focus on DeMar.

Every Raptors fan, on some level, owes the man a debt. Whether or not you ultimately loved his game, he stuck with us in the post-Chris Bosh era, remarkably improved each and every season and left everything on the court. He inspired me, over three years ago, to write a piece comparing him to the tortoise, of tortoise-and-the-hare fame. He continued that trajectory afterwards, turning himself into a perennial All-Star and an All-NBA player.

His passion and dedication to the game cannot be questioned. His love for Toronto and seemingly for us, his fans, was unrelenting.

So when the following is reported:

It’s understandable that as a fan, you’d have some questions for team management. Even some doubts about how the whole thing was handled, or whether it was the right move at all.

After all, this is a guy who re-signed without even taking meetings elsewhere. Who gave us his sweat, his blood and his soul. Who said ‘I got us’ and really meant it. Who by all accounts, wanted to be a Raptor for life.

Ujiri apologized to DeRozan in his press conference Friday, citing ‘a miscommunication’. While it was the prudent thing to do, should he have even had to apologize? Was what Ujiri wound up doing to DeRozan, while a clear win from a short-term basketball standpoint, wrong on some type of moral grounds? Was it disloyal? Is Lou Williams right?

It all comes down the question of how you define loyalty.


DeRozan was drafted by the Raptors in 2009. He made his first all-star game in 2014. He made his first All-NBA team in 2017.

We’ve consistently lauded him, in this piece even, for the consistent improvements he made to his game, his dogged determination to get better. But how much more room was there to grow? And perhaps more importantly, how long was it going to take?

Ujiri officially returned to Toronto on May 31st, 2013. When he took over as the team’s general manager, Dwane Casey was already the coach, Kyle Lowry was already the point guard and DeRozan had already been signed to his first contract extension.

Despite leaning towards blowing things up (and nearly doing so), when Ujiri found unexpected success by dealing Rudy Gay to Sacramento, he rolled with it. He extended Lowry, the problem-child turned star — twice. He extended Dwane Casey, even after a first-round exit to a lower seed, in Brooklyn. He kept him on again the following season, despite an ugly sweep at the hands of Washington. He also nearly maxed out DeRozan, a beloved and talented player, but one with clear flaws on both ends of the court.

He did all of that, despite the fact that every spring, Raptors fans had to wait with bated breath to see if their team would actually show up come playoff time. If another freak injury or unexplained no-show in a key game would derail their lofty goals.

He rode for them, defended them to any and all, and nobody was happier than Ujiri when they finally won a playoff series versus Indiana.

Is that not loyalty?

One might argue that it wasn’t really, that it was simply the best chance for team success, and they would have something of a point. But if you’re searching for true altruism in the NBA, you’re going to come up empty.

Ujiri could have blown this entire thing up at any time. He chose not to, despite the fact that the core and the coach were not the ones that he had selected himself. He opted to put team success ahead of his own ego, to give these flawed but dedicated players a platform to succeed on the biggest possible stage.

Despite their best attempts, despite many moments that will live on in our minds as fans forever, ultimately, they were given that opportunity and they failed.

Even remembering that they had tremendous regular season success, come playoff time, everything seemed exponentially more difficult. Even during the now fondly-remembered run to the Conference Finals, the games were more “butt-clenching rock fight” than “beautiful game”.

Ujiri does not have the luxury of reveling in those achievements, such as they are. His job is evaluating the roster for weaknesses and doing everything he can to improve the team. He did everything he could to do so with the core of the past five seasons.

That’s right, five seasons.

Masai Ujiri returned to the Raptors on May 31st, 2013. Just how long, exactly, was he supposed to wait?