DeMar DeRozan an unfortunate casualty of Masai Ujiri’s title ambitions

Michael Grange takes a look back at the career of DeMar DeRozan with Toronto Raptors.

There is a 10-hour time difference between Nairobi, Kenya and Los Angeles, California.

As the final pieces of the biggest trade Toronto Raptors president Masai Ujiri has ever made, and likely will ever make, fell into place, it was about 2 a.m. in Nairobi on Wednesday, the middle of the day on Tuesday in L.A.

Ujiri’s job required him to make a phone call to DeMar DeRozan and tell him he was being traded.

He had to tell the franchise icon and the most loyal player the Raptors have ever had that his services were no longer required. That it was better to risk everything on the possibility that Kawhi Leonard will arrive in Toronto healthy, happy and ready to win — even for just one season — than stick with the status quo after five years of playoff highs and ultimately lows, an era intimately identified with DeRozan, whose only ‘sin’ was committing everything to the franchise and everything to turning himself into a two-time all-NBA player, lifting the only NBA team he had ever known to new heights in the process.

But now? Not good enough. No matter how the conversation went, that was inescapably the message.

The Raptors were at an impasse, their 10-game post-season losing streak spread over three years to LeBron James and the Cleveland Cavaliers the evidence.

Of their core pieces, DeRozan was the most marketable, for his skill, his health and his age.

Around the league, Leonard — available due to a surprising unravelling in San Antonio — was their best option to make a breakthrough, despite the risks of taking on an injured, disgruntled player with only one year left on his deal.

According to multiple league sources there had been some feelers — and not for the first time — about the availability of Andrew Wiggins from Minnesota; there were inquiries about trying to move into the draft lottery with DeRozan a carrot for teams that have playoff aspirations — Memphis, Dallas and the Los Angeles Clippers would fit that bill.

But there was no traction and it’s not clear how, if or when those moves would have advanced the mission of winning in Toronto.

The decision to push forward on Leonard was made, the opportunity provided by the air coming out of the market for the All-NBA forward after LeBron James signed with the Los Angeles Lakers independent of any assurance that he be joined immediately by another star.

Suddenly the Raptors were at the front of the line and confident on pushing back on requests for OG Anunoby, the team’s top-rated young prospect, and on demanding top-20 protections for their 2019 first-round pick.

But that wouldn’t have made telling DeRozan any easier.

Leadership is not a job for the weak of heart, especially if you have one.

Ujiri has one. Spend five minutes with the man and it’s evident. He nearly came to tears when he announced he was firing Dwane Casey last month.

“I don’t think I’ll work with a better person — maybe my dad,” Ujiri said then. “…To be honest, in our business, you value real people, people that look you in the eye and tell you, and you know what they’re telling you is what they’re telling you. That’s coach Casey, a good man, a good ball coach.”


So imagine the burden of having to tell DeRozan he was surplus. You can picture Ujiri pacing around his hotel room in the middle of the night before tapping on DeRozan’s number.

You can understand DeRozan’s hurt on hearing the news. The anger; the apparent belief that he had been lied to after having been — in his mind — advised only days before that he was not going to be traded.

Those feelings won’t be subsiding anytime soon, and how DeRozan chooses to share them, and in what context — he’s not ready to speak publicly for the moment, according to sources close to the four-time all-star — remain a trip wire in this whole thing.

He’s one of the best-liked and most respected stars in the game, a friend of many and enemy of none.

If he chooses to go scorched earth, his message will be heard around the NBA and it will resonate. Only winning will drown it out, and there are no guarantees there.

Logically, there is no upside in Ujiri getting into a back-and-forth on exactly what was said between him and DeRozan or him and DeRozan’s longtime agent, Aaron Goodwin.

What Ujiri might have communicated in meetings in Las Vegas with DeRozan and Goodwin, and what they interpreted, is almost irrelevant, short of a transcript being provided. Although the notion that Ujiri gave a ‘no-trade’ assurance seems unlikely given his habit in previous years in meeting with agents has been to leave all possibilities open regarding roster moves.

It only makes sense. Why paint yourself into corners?

The Raptors’ initial conversations with Leonard and his camp were positive, according to league sources — although there are others in the league saying that Leonard has been emphatic about not wanting to play here, and not wanting to stay here, and is already looking at building alliances with other stars in free agency in the summer of 2019, even though the Raptors can pay him $49 million more than any other team.

But the decision to trade DeRozan and take on the risk inherent with Leonard suggests the mindset of an executive determined to push the envelope, to take big risks in the name of forcing his team through a window of opportunity that won’t remain open very long.

It’s about answering every question with: ‘Will it bring us closer to winning?’

That kind of calculus can be harsh and requires decisions that take a heavy toll on relationships, on reputations, and yet come with nothing written in stone.

The Raptors have been climbing a mountain the past five years, with DeRozan pulling his share of the weight. Each year, even after seasons that end in losses, there has been reason for optimism, that the best was ahead.

But as you get close to a summit, the oxygen gets thinner. Every step harder. The choices more difficult, the consequences more severe. The comfort of base camp further away, and not everyone gets to the top. Winning isn’t for everyone and not everyone wins.

Masai Ujiri made a phone call from a continent away to his star player, and began his ascent.

There is no turning back.

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