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The Raptors traded for Kawhi Leonard knowing newcomers always fall in love with Toronto

GM Masai Ujiri bet big on Toronto’s ability to convert transplants when he traded DeMar DeRozan for Kawhi Leonard.

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

Raptors GM Masai Ujiri tried to get out ahead of it. He opened Friday’s press conference at Scotiabank Arena with a three-and-half minute statement that began with an apology to DeMar DeRozan, “for maybe a gap of miscommunication but also to acknowledge him and what he’s done with the Raptors, for this city, for this country” after reports surfaced that DeRozan was assured during a meeting at summer league that he wouldn’t be traded.

He was, of course, alongside Jakob Poeltl and a protected first round pick to the Spurs in exchange for Kawhi Leonard and Danny Green.

Ujiri added that DeRozan would be celebrated “the best possible way we can,” waxed on the difficulties of the human side of the business, thanked Poeltl and expressed his excitement about bringing Leonard, “a top-five player” and Green into the fold.

Ujiri just got off a plane from Africa. He was running on two hours of sleep, but he looked every bit like the shrewd manager hell-bent on dragging Toronto’s ambition’s up to his.

And then a reporter asked him what exactly he was apologizing for, setting the terms of the afternoon. Ujiri’s attempts to be vague were answered by repeated questions on the nature of his conversation with DeRozan, and he ended up apologizing twice more. He was sweating. At one point, he knocked a water bottle off the podium, giving way to a version we have rarely seen publicly: transparent, revelatory, a little nervous, even incredulous.

“I hate to be defensive here,” said Ujiri, “but I can also say when I came here, I gave them 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.”

Toronto Raptors v Cleveland Cavaliers - Game Four Photo by Jason Miller/Getty Images

“It’s hard to satisfy everybody in our position. If we didn’t do anything, I think everyone would comment that it’s the same team, so what’s the difference? We’re going to play the regular season and we’re going to get beat again in the playoffs. That would be the narrative.”

Accurately gauging fan reaction is almost impossible. No city-wide poll on the trade has been conducted, but social media suggests most people are upset, not only that DeRozan — the first star to stay in Toronto voluntarily — was traded, but how he was traded, and that it was for somebody who reportedly has little interest in staying. The trade sprouted the worst fears of every fan who grew up cheering for the Raptors through the dog days. But Ujiri isn’t from the city, and doesn’t have the same negative experiences that some locals may have. The Raptors, in his tenure, have been defined by unprecedented progress. He thinks they’re worth betting on.

“I think there’s a lot to sell here. Our team, our culture, our city, our ownership. We have everything here except a championship, in my humble opinion. We have great fans, we have a great organization, we have a great following, I think we have a great country. There is something about this place that reaches out to the whole world and we’re proud of that and we’re going to continue to sell that. Hopefully it’s an appeal, not only to him but to more NBA players,” adding that Leonard “didn’t express a lack of interest about playing in Canada to me.”

To this day, when Ujiri talks about Toronto, he sounds mystified. I get the sense that he believes the city can be sold to Leonard because not so long ago, it was sold to him.

As somebody who moved to Toronto less than a year ago, the picture in my head was of a monochromatic finance-obsessed city that was only interested in convincing everyone else that they’re no longer little brother. Now, it’s hard to imagine ever leaving, or having to ‘sell’ Toronto, a cosmopolitan hub, a coastal media-heavy city that lives on the intersection of multiculturalism, sports, music, entertainment, opportunity and nightlife.

Toronto’s place in the public consciousness has blown up alongside the success of the Raptors, the Leafs, the Blue Jays, Drake, The Weeknd — you name it. The people who have lived here a long time have witnessed that growth first-hand, and they likely understand it better than I could ever hope to. But they also lived through the Vince Carter-era, and suffered the indignity of hearing Chris Bosh say he couldn’t even get NBA League Pass there, making Toronto sound like a barren landscape without WiFi or airports. The inferiority complex is local, but it exists for a reason.

San Antonio Spurs v Golden State Warriors - Game One Photo by Thearon W. Henderson/Getty Images

Now, when I tell people I live here, their eyes light up. They drool about favorite restaurants, some tucked-away dim sum spot they discovered, running alongside the harbour, walking down College Street and accidentally stumbling upon Kensington Market, discovering pocket after pocket in a city that has something for everyone, including rich superstar athletes. The Cavaliers partied with Drake for three days when they came to Toronto.

But L.A. nightlife, the saying goes, is undefeated. That’s what the Raptors are contending against: a city that offers a great deal of what Toronto does, with better weather, LeBron James, the Lakers, Magic Johnson, and majesty. The Clippers loom large as well.

Alongside how far the Raptors can go in the playoffs, Ujiri’s gamble will come down what Kawhi Leonard — whose desires nobody has been able to pin down — wants. If Leonard is hellbent on going home or building a superteam in New York, that’s the ball game. But if there’s even a sliver of hope that he might want something else, something different, he might just find it in Toronto.

After all, he wouldn’t be the first Los Angeles-born All-NBA wing to pledge his loyalty to the Raptors.