
Kyle Lowry made it Instagram official, but I still can’t shake the thought: What if Lowry doesn’t get traded? What if, because the deal was telegraphed a day in advance of the official opening of free agency, the league reverses the sign-and-trade sending Lowry (signed to a new three-year, $90 million deal) to Miami in exchange for a package based around Goran Dragic and Precious Achiuwa?
It would be a fitting coda to the Lowry era in Toronto—one more time he almost got traded, for old times’ sake.
Lowry arrived in Toronto via trade in 2012 as a consolation prize after former GM Bryan Colangelo failed to attract an aching Steve Nash back to Canada. Toronto was supposed to be another pit stop, like Memphis and Houston, where he was misunderstood, his skills underutilized by both the people around him and himself. Instead, he and the franchise found home in each other.
The first time the Raptors didn’t trade Lowry, it was the morning of Friday the 13th. After taking over for Colangelo, Masai Ujiri sought to trade Lowry in order to embark on his search for a franchise savior. But Knicks owner James Dolan, afraid of creating the perception that he’d been “fleeced” yet again by Ujiri, stopped engaging in trade talks.
That night, the Raptors played the Sixers, and with 3.9 seconds left on the clock in the third quarter, Lowry let the ball roll up the floor all the way to the end of the logo, using his body as a moving protective cage, eyes wide open on a swivel, baiting his defender, Tony Wroten, to match his attention span.
The second Wroten got up close to pressure the ball, Lowry picked it up, went left and went fast, and gave himself enough time to miss and then put it back in the lane. The bucket put the Raptors up seven and gave Toronto its first glimpse of the future: Lowry’s gift of concentration, his ability to see everything and thereby manipulate the defense.
He was less refined physically, emotionally, and tactically, but the kernel of the player he would become was there, and the Raptors got lucky enough to explore it. Lowry and DeMar DeRozan blossomed into All-Stars and led Toronto to the playoffs, where Lowry’s ability to stretch a second finally met a moment that mattered.
The Raptors won Game 5 of their 2014 first-round series against the Nets by just two points. Paul Pierce would have the last play, though—knocking Lowry’s floater out of the air and securing a win in Game 7—and the last say. A year later, he helped the Washington Wizards sweep the Raptors and declared that they didn’t have “it.”
Lowry’s take on his early playoff struggles is that they were never as bad as they seemed. The Raptors’ crunch-time mishaps were top of mind for fans, but he also did things not everyone could see. These days, there is a sense that Lowry can make anything cohere. Lowry was the first domino to fall in a free-agent class full of playmakers. Multiple teams with championship aspirations—the Lakers, Sixers, and Clippers, as well as would-be contenders like the Mavericks and Pelicans—wondered whether the guy who once didn’t have “it” could help them get to the promised land.
But Pierce had a point: The Raptors and Lowry were still figuring out who they were, what they could be.
Lowry showed up next season, in 2015-16, 15 pounds lighter, but the Raptors lost to the Cavaliers in six games in the Eastern Conference finals, ushering in the LeBronto era. When the DeRozan-Lowry duo finally ran out of rope with Ujiri, Toronto speculated on trading both, but in the end, DeRozan was who it was willing to give up for Kawhi Leonard.
Lowry’s information-processing ability allowed him to accumulate tiny, winning edges that didn’t show up in the stat sheet, but he had yet to master his superpower off the court. The guy who just won’t stop talking on the court used to sulk in the corner when he wasn’t in the game. He didn’t know he could make other people see what he saw. He was a point guard, not yet a floor general. When the Raptors shipped away his best friend, Lowry ghosted Ujiri and new coach Nick Nurse for weeks. He was the same old Lowry in games, but he was disengaged, lips zipped tight in a role that requires communication.
In the days leading up to the 2019 trade deadline, just months before he hoisted the Larry O’Brien trophy, Ujiri could have tried to send Lowry to Memphis for Mike Conley, in the deal that exchanged Jonas Valanciunas for Marc Gasol. Instead, the two sat down for their first real conversation in months.
If you want to measure his growth from that point, do it through the contours of his smile, which started taking on a form we’d never seen in public.
There’s the finally-made-it-to-the-Finals smile ...

… and the just-won-the-Finals smile.

The biggest one, however, came in the bubble last year. The Raptors had half a second on the clock; Lowry, inbounding the ball, launched a rainbow pass over Tacko Fall’s outstretched arms. The ball landed right in the shooting pocket of OG Anunoby, who nailed a game-winning triple against the Celtics in Game 3 of the Eastern Conference semifinals.
That’s the smile of a man getting to do what he was designed to do.
At the trade deadline last season, the Raptors were working to send Lowry and his expiring contract to a team that could contend for a championship. His departure felt all but imminent, so much so that after blowing out the Nuggets in what could have been his last game in a Raptors uniform, he was feeling nostalgic enough to not, in his words, “bullshit” reporters after the game.
“I was literally trying to figure out who I was,” Lowry said about the version of himself that arrived in Toronto. “Now it’s like, how do I help everyone else? I’m not looking to just help me. I’m good. I wanna help everybody else. That’s the maturation of what I feel like I’ve become. I wanna help the world, and I can help the world because I’ve been through so many experiences: the good, the bad, the highs and lows, and I know I can help anybody.”
He has become exactly who Miami needs: a buttoned-up professional with thousands of reps running a high-level NBA offense, a veteran who has also found joy in shepherding young players. He can rip off double handoffs with Bam Adebayo and hit precise pull-ups. If Tyler Herro is anxious to make a shot, he can set him up on the court and pull him aside off it.
Lowry spent so much of his Raptors tenure on the trade block that, at times, it felt like they just didn’t believe he could get them where he needed to go. But it was also an affirmation of his value, a stubborn insistence that he was worth more than what rival executives thought of him. “I hope I’m pardoned if I valued him too much,” Ujiri said after the deadline, admitting the Raptors were extremely biased when it came to Lowry. In hindsight, they had it right all along.