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2018-19 Player Preview: Masai Ujiri

Looking at the boss.

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Masai Ujiri’s Toronto Raptors won 59 games and the No. 1 seed in the East last season. They’ve won at least 48 games in each of their last five seasons, proving elite at balancing a win-now timeline while simultaneously building for the future by drafting and developing young talent. Under Ujiri the Raptors have become a legitimate top-tier NBA franchise with strong leadership, exceptional resources and facilities, dedicated fans, a winning culture, and with the addition of Kawhi Leonard, a superstar player and a legitimate chance at taking the next step forward to achieving success beyond the regular season. It’s no wonder, then, that Ujiri is frustrated with the ongoing perception that Toronto is still an inferior market.

“The narrative of not wanting to come to this city is gone,” Ujiri told reporters on media day. “I think that’s old and we should move past that. Believe in the city, believe in yourselves. First of all here in Toronto we have to believe in ourselves. We should stop talking about coming to this city or wanting to come to this city. That’s old talk… We are proud of who we are.”

Ujiri was referring to the perception around the league that the Raptors are unable to sell superstar players on Toronto, like newly acquired wing Leonard, for example, but he was also referring to something much more personal: The pessimism Torontonian sports fans carry with themselves and project onto their teams. Ujiri is proud of what he has built in his five years as President of the Raptors, taking the franchise from average to elite, and he wants fans and media to appreciate what the Raptors have become.

As longtime Raptors broadcaster Jack Armstrong puts it:

Top to bottom, this is one of the elite franchises in the NBA. In my time here, this is the best shape I’ve seen the organization in. There’s committed ownership, outstanding leadership, sound coaching and a top-notch support staff. The team plays in front of incredibly loyal and passionate fans in a sold-out downtown arena in the heart of a world-class city. Every game is televised on national TV and the team has a rabid following from coast to coast. Toronto is the third largest market in North American sports. This place has always been a sleeping giant and now it has come into its own.

Ujiri helped turn the Raptors into an elite NBA franchise. Now comes the hard part: Convincing the city that the Raptors are for real by bringing home a championship.

Winning an NBA Championship has always been Ujiri’s ultimate goal; It’s what sets him apart from other General Managers in the league who rather play it safe to keep their job than take a risk by going all in.

As Jalen Rose put it, “Fifty percent of the NBA teams have never won a championship [including Toronto]. And most of them never go for it truly because it’s usually safer for the GM to play the long game versus the short game.”

Ujiri is done accepting mediocrity. He wants to be the guy to bring the Raptors their first championship in franchise history and Toronto its first major sports championship since 1993 (when the Blue Jays won). Trading DeMar DeRozan for Leonard this past offseason was the ultimate swing for the fences; a shortsighted move that abandoned mediocrity for a chance at competing for an NBA Title now while risking implosion afterwards if Leonard walks. Firing Dwane Casey and replacing him with longtime assistant coach Nick Nurse may seem conservative, but was actually a risky move to empower one of the more progressive, forward-thinking minds in basketball.

“We want to win a championship,” Ujiri clarified after the blockbuster trade that moved DeRozan out for Leonard. “I hate to be defensive here, but I can also say when I came here, I gave (Casey, DeRozan and Lowry, amongst others) a chance. I could have done anything I wanted… I could have traded players. We kept giving them a chance and giving them a chance. At some point, we have to do something different.”

With the 2018-19 season just weeks away, Ujiri is not necessarily in the hot seat, but he certainly has more pressure on him than ever before. He has built what appears to be the best team in Raptors history, but the only thing that will justify his actions — trading DeRozan for Leonard and replacing Casey with Nurse — is getting over the hump and winning. In fact, winning is the Raptors only real goal, because the team has to make a deep playoff run this year if they want to resign Leonard once his contract expires at the end of the season.

“By winning games, this is how you get star-calibre players to want to come here and play,” Leonard acknowledged.

The Raptors already have the deepest and best roster in history (on paper), but Ujiri’s work isn’t done. In order to make a deep run in the postseason Ujiri would be smart to push his chips in even further, continuing to upgrade the roster by trading for a third star like Jimmy Butler or someone else who becomes available before the trade deadline.

“We’re happy with this team,” Ujiri said. “We still have a lot of the players that we have and the combination of the players we have, we are confident. If any of them moves or deals come our way that make sense for our team to get better and to win a championship, I think we have to look at that. Because there is a certain window, and we acknowledge that.”

Over the past five years, Ujiri has built an infrastructure that can go toe-to-toe with the NBA’s best. The Raptors have strong leadership, outstanding resources and facilities, progressive coaching and support staff, devoted fans, and a winning culture. That will all help sell Leonard on Toronto, but Toronto needs to believe in itself first.

“There is an unbelievable thing here. There’s a goldmine here. Maybe people here can understand that and feel more proud about that,” Ujiri said. “I don’t understand what there is (to be worried about) here.”

Torontonians will be worried until they get their long coveted championship. The city has lost for so long and grown so accustomed to losing, pessimism and worry have become the nature of sports fandom in Toronto. But if the Raptors win, if Leonard stays, and if Ujiri’s actions are justified, maybe the cup half-empty, inferior market complex that surrounds Toronto will disappear along the city’s championship drought.

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