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Let’s embrace the Toronto Raptors’ future, with help from DeMar DeRozan

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After an emotional night against their former franchise cornerstone, the Raptors and the city of Toronto can now fully reflect on their past... and their future.

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NBA: Boston Celtics at Toronto Raptors Nick Turchiaro-USA TODAY Sports

DeMar DeRozan’s first game back in Toronto since he was traded to the Spurs had an uncanny, dreamlike feel. The poetic symmetry inherent in the DeMar DeRozan-Kawhi Leonard trade meant it was destined to be an emotional night; from a narrative standpoint, the two were almost photo negatives, each one’s strengths highlighting what the other seemed to lack. DeRozan is a complex, vulnerable figure who’s been unprecedently open about his emotional life, and his personal journey from rookie to All-Star was so completely intertwined with the growth of this city that he literally made himself its metonym. Leonard, meanwhile, is a charming but completely inscrutable superstar with zero commitment to this city past the end of this season, and an inner life so comically opaque that it’s become a meme.

Trading the former for the latter was a clear statement of priority: DeRozan’s ability to grow as a Raptor seemed to have plateaued, but his dedication to the team over the years was what had made it into the kind of franchise that could afford to turn him loose in the first place. It’s just business, a lot of people said after the trade went through — which is either an excuse or an indictment, depending on how you feel.

The trade may have stung at the time, but no one can deny it’s been exciting to have Leonard on the Raptors. His presence has given the team a new momentum, and DeRozan is playing some of the best basketball of his life — so maybe there’s nothing to feel weird about after all. Still, as coach Nick Nurse himself admitted on Friday, the Raptors’ first messy loss to the Spurs back in January revealed some leftover emotional baggage. There’s a real risk in charging forward into the future before you’ve fully reconciled with your own past. If you’re not careful, you can end up haunted.

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During a press conference on Thursday night, DeRozan joked that one thing he didn’t miss about Toronto was all the construction. In the past decade — a timeline that roughly tracks with DeRozan’s own stint as a Raptor — Toronto has been razing, rebuilding, and “revitalizing” itself at near-warp speed. The construction is particularly gnarly around the Scotiabank Arena, a 20-year-old building that got its new name less than a year ago, and its own tribute video right after DeRozan’s and Jakob Poeltl’s on Friday night. The stadium abuts a mess of half-built high-rises, and sits just above a shifting waterfront that seems to grow a fresh layer of developments every week. Whenever I see the skyline from the airport or a ferry, I can still make out the shape of the city I grew up in — but only if I squint. The Toronto of my past shimmers in and out of the one I live in now like a mirage, refracted inside all that brand-new glass.

None of this is necessarily bad. Every living city changes, has to change to stay alive. But for all its projection into the future, Toronto’s always felt a little haunted to me — like it’s never totally figured out how reconcile its origins with its ambitions. I think about this every time a local landmark gets bulldozed to make room for more condos, every time I walk into a brand-new bright-white café that’s mounted the signage of an old business up on its walls.

Maybe some of this is just projection. I’ve lived in the same neighbourhood on and off for a cumulative 21 years now, and sometimes, walking down a familiar street, I’ll spot a new building spliced in between two old ones and feel a split second of ghostly unease, like I’ve come untethered from the linear progression of time. DeRozan described a version of this feeling at his press conference on Thursday night — how even just seeing a baggage handler he recognized on the flight in had sparked a strange, uncanny sense of repetition. It seems like just yesterday I was here, he said. Is this just what happens when you’ve lived in the same place long enough to see it shift? Or is there something about Toronto, specifically, that engenders this feeling — of the boundaries between the past and the present getting lighter, dissolving entirely?

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Nostalgia is one kind of time travel; anxiety’s another. DeRozan has, of course, been famously open about his struggles with mental health both on and off the court. Maybe this, too, is projection, but I always felt like his emotional openness was an essential feature of his closeness with Raptors fans — just as important as his love for the city, if not more. On the court, his feelings often floated so close to the surface that the boundaries between him and the game he was playing seemed to dissolve entirely. When he struggled or stuttered, you didn’t just see it on his face — you felt it in your own body too, like someone was wringing out your nerves. Likewise, in the moments when he managed to untether himself from all context and go weightless, you caught a contact high — the giddy, soaring relief. This was, to me, the real pleasure of watching DeRozan play for the Raptors: it felt like watching a human being struggle in real time with the endless challenge of existing in the present, his effort collapsing the distance between himself, the game, and the city he was working to represent.

I thought about this a lot during the first few minutes of Friday’s game. I thought about it every time he touched the ball, when the reflexive roar that rose up from the crowd sounded less like a chorus of human voices and more like a tornado touching down inside my skull. And I thought about it during that first time-out, when they played his tribute video on the big screen. On the TV broadcast, they ran it splitscreen with a steady close-up of DeRozan’s face, so you could watch him watch himself moving in fast-forward through ten whole years of his life. It felt heart-rending to see. After all, so much of the work of being clinically anxious is just trying to turn off your own personal version of this video: the rapid-fire montage of moments from your own life that plays on a loop in your mind, threatening to drown out the present and drag you back into the endlessly repeating past.

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I’ve been thinking a lot about Kyle Lowry’s pre-game handshake — the one he used to do with DeRozan but now performs alone, against the air where his best friend used to stand, before the start of every game.

The first time I saw it, I found the routine almost unbearably heartbreaking; it seemed like the loneliest thing I’d ever seen, a man shaking hands with a living ghost. But the more I think about it, the more it seems like a gesture of defiance — like a refusal to allow DeRozan to be erased from the team that was so quick to give him up.

It seems fitting, then, that while Kawhi scored the last dunk on Friday, it was Lowry — firmly grounded in the present, but highly aware of the past — who ultimately brokered the game’s impossibly elegant, highly symbolic turn. Lowry always plays like himself, but his superpower is his ability to vibrate sympathetically against his teammates — to match the pitch and pace of his own play to theirs. When DeRozan was a Raptor, their on-court chemistry always felt inextricable from their friendship; since his departure, Lowry’s been building a more subtle, simmering kind of chemistry with Leonard. It made almost too much sense that Lowry would use his understanding of both men to execute the game’s last turnover — literally fitting himself between the two of them, bridging the gap.

On paper, you could read that play as a disappointment for DeMar; technically, of course, it meant a loss. But after the game he seemed happy, almost relieved — like the symbolic weight of the whole night had finally been lifted off his shoulders, even as the strangeness of the whole thing persisted. “Walking off the floor,” DeRozan said, “it hit me more than anything. Just a feeling of knowing what it’s like walking off that floor, whether it’s from playoff games — the good, the bad, the ugly.”

DeRozan was talking about the Toronto of his memory, shimmering in and out of the one he was walking through in the present. In the end, this game felt like a reminder that there is more to be done with the past besides just ignoring or repeating it. Play it right, and your past can propel you forward — into a future that’s somehow strange, familiar, and old and new, all at the same time.