One bit of lore from Kyle Lowry’s legendary, nine-year run with the Toronto Raptors: Shortly after they acquired him in July 2012, Alvin Williams told him that, if he could lead them to the playoffs, he’d be remembered in Toronto forever.
That sentiment, reported in 2014 by Adrian Wojnarowski, then of Yahoo Sports, seems quaint now. The playoffs? That’s it?
At the time, though, the Raptors had missed the playoffs in eight of the previous 10 seasons. And they hadn’t won a playoff series since the first-round victory against the New York Knicks that Williams clinched with a crunch-time jumper at Madison Square Garden in 2001.
Williams, then working in Toronto’s front office as a scout and director of player development, had felt a connection to the city since his playing days. He was well aware, though, that many players viewed it as a “pit stop,” rather than somewhere to put down roots.
“People thought they could use Canada and the Toronto Raptors as some way to elevate their game, so they can go somewhere else to play in the States,” Williams, now an analyst for Sportsnet, said. “A lot of people love the city, but when it came to the franchise, before it became really stable and management and ownership and the coaching and everything became more solidified, Toronto was a very shaky place for someone’s career at that time.”
Lowry himself has said that he initially saw Toronto that way, too. It turned out, though, to be the right place for him. It is where he became a perennial All-Star and, eventually, a champion. On Tuesday at the team’s practice facility, he signed a one-day contract to retire as a Raptor after 20 seasons in the NBA. Toronto announced that his No. 7 jersey would be retired next season, and that it would hold a charity golf tournament, a block party and a gala in his honor in September.
How Lowry earned Canada’s love ‘forever’
Both the team and mayor Olivia Chow, who officially proclaimed July 7, 2026, as “Kyle Lowry Day,” referred to Lowry as “the GROAT,” i.e., the Greatest Raptor of All Time. “In many ways, I think of the franchise before Kyle and sort of after Kyle’s arrival,” team president Bobby Webster told reporters at a Tuesday news conference. Before the “GROAT,” Toronto had no 50-win seasons and just one playoff series victory since its first season in 1995.
With the GROAT, it had five consecutive 50-win seasons, nine playoff series victories and an NBA championship.
Williams said, “When I had the conversation at my house, it was just more so talking to him about Toronto, talking to him about the opportunities.” Williams told Lowry that, as the only team in Canada, the Raptors offered players a unique situation. Fourteen years later, Lowry was sitting at a podium, talking about “playing for Halifax, Calgary, B.C.,” and repeatedly referring to Toronto as “home.”
Williams was more right than he ever could have dreamed.
“[I told him,] ‘This is your entire country, so you can really make an imprint, and if you end up winning here’ — and I didn’t even think of a championship — ‘if you just end up winning and having a winning pedigree, man, they’ll love you forever,'” Williams said. “Because I knew the type of person he was. I knew his style of play. I knew he was aggressive. I knew he was a hard worker, and we had some similarities in our approach and playing in that way at that time, so I just knew that he would really be appreciated, and he could really, really make an imprint on the country and that team if he was able to be a part of them winning. I didn’t know he was gonna be a huge part of them winning the ultimate prize.”
Before Game 6 of the 2019 NBA Finals, Williams, a fellow Philadelphia native and Villanova alum, talked to several people in Philly who had known Lowry even longer than he had. “They all had the same story,” he said. In a game like this, Lowry will play his ass off, just like he did when he was going up against a big-name player in AAU or when a college coach came to watch him.
Sure enough, Lowry started the game on a personal 8-0 run. He had 21 points, six assists and six rebounds at halftime. “I wasn’t surprised when I saw how focused he was and how aggressive he was to start that game,” Williams said. Days after missing a chance to win the title at home, Lowry set the tone for the biggest win in Raptors history.
Webster called it “my most memorable and happy moment” of the Lowry era. At halftime, he told reporters, Webster thought about “all the doubters and the haters and all the people who didn’t think Kyle could win one.” The funny thing about Lowry’s storybook arc in Toronto, though, is that it could have taken a different turn on multiple occasions.
On their way to the title, the Raptors fell down 2-1 in the Eastern Conference semifinals against the Philadelphia 76ers and escaped in Game 7 thanks to Kawhi Leonard’s game-winning shot, one of the most iconic and preposterous buzzer-beaters in NBA history. They fell down 2-0 against the Milwaukee Bucks in the Eastern Conference Finals and won Game 3 in double overtime.
Before all that, Toronto “had the Kawhi [Leonard] trade,” Webster said, “we had the [Marc] Gasol trade, I think we even had a maybe-Kyle trade.” Mere months before the playoffs started, Lowry’s name came up in trade talks with the Memphis Grizzlies.
Lowry famously had his bags packed early in his second year with the Raptors before Knicks owner James Dolan nixed a trade that would have sent him to New York. That’s when Toronto began its upward trajectory, but there would be more turbulence in his tenure. There were rumors he might leave in free agency after the Raptors were swept by the Cleveland Cavaliers in the 2017 playoffs, but re-signing ended up being his best option. It was hardly a secret that he was upset with the organization for trading DeMar DeRozan after another sweep at the hands of the Cavs the next year.
“I don’t know what you’re talking about. Me and this organization has always been eye to eye, we’ve always been on the same page,” Lowry told reporters with a smirk on his face on Tuesday. “Always.” Then he praised the Raptors for putting him in a position to go all the way, which he called the biggest accomplishment of his career.
“I played to win, and that’s all I really cared about,” Lowry said.
To Williams, the fact that Lowry stuck around as long as he did is a testament to his growth. “If you look at Kyle Lowry right now, you would never think he went through all of those things, right?” he said. Williams remembers that, in Lowry’s early days in Toronto, he “wasn’t the easiest person to get along with.” When he was bumping heads with then-coach Dwane Casey, Williams called him out.
“I asked Kyle, just flat out, ‘How many of your former coaches can say anything good about you?’ Like, you have to consider that it’s not everybody else’s fault,” Williams said.
A man on a mission
The first time they met, Williams thought Lowry was a jerk. Lowry was at Villanova on an unofficial visit with his high school teammate Shane Clark, and Williams was there working out with his former teammate Jonathan Haynes. Then-Wildcats coach Jay Wright asked Williams and Haynes to go talk to Lowry.
“I just simply went up to him and just said, ‘Hey man, how’s the recruiting process?’ And this kid didn’t even look at me. He just was like, ‘I don’t talk about that, he talks about that,’ and he gave a head nod over to his high school coach or somebody that he was there with,” Williams said.
That was the end of the conversation. “I didn’t like him,” Williams said. The next time Williams saw Lowry, he was shooting by himself in the gym at Villanova on a torn ACL. (The injury had taken place in a pick-up game; he hadn’t had surgery yet.) The two chatted, and, once Lowry got healthy, they scrimmaged against each other. Lowry’s competitiveness stood out immediately, but Williams didn’t understand how serious he was until learning that he’d been doing regular workouts with Jameer Nelson at around 5 a.m. Williams came to the conclusion that Lowry was “not just the snotty-nosed young punk that I thought he was at first,” but a young man on a mission.
All along, Lowry remained brash and fiery, even in his late-career stint with the 76ers. Williams, however, saw him improve his attitude and take his health and nutrition more seriously as his professional career went on. When the Raptors visited Philadelphia, he’d have the entire team over for dinner.
There was a time that Williams was “supposed to be, like, the Kyle whisperer” for the team, Williams said. Now, though, “I do more listening to Kyle than I do speaking with him ’cause he’s so mature, he’s so well versed in so many different things. He helps me out as the little brother now more than I probably helped him out as the big brother back then.”
Looking back, Williams said, it is “amazing to see where Kyle has come from.” After his fourth year in the NBA, Lowry was a 26.3% career 3-point shooter. The way the league was going, this wasn’t going to fly, especially as a point guard on Daryl Morey’s Houston Rockets. The next season, Lowry drastically increased his 3-point volume and efficiency (37.6%). He built on that in Toronto, where he became one of the premier pull-up threats on the planet.
Between the 3-point shooting, the playmaking, the on- and off-ball defense and his commitment to exploiting every little edge he could find, Lowry became an analytics darling and a bona fide star. “His IQ is off the charts,” Williams said. He studied opposing teams’ sets, knew opposing players’ tendencies and put his teammates in their proper positions. He took multiple charges in the All-Star Game. (On Tuesday, Lowry told reporters that the one he took against Leonard in Chicago in 2020 was the favorite charge of his career.)
“He’s just going to bring winning to your team,” Williams said. “With the IQ mixed with that, he’s just a complete player. He may not be the flashiest, but you have your Kyrie Irvings and your Steph Currys, and these guys that are just driving you insane with their talent and everything they can do — I’m taking Kyle Lowry all day because he’s playing on both sides of the floor and he’s the type of guy that’s going to make those type of guys work.”
The point is not that Lowry is the best point guard of his generation, but that, at 6 feet tall and without elite burst or bounce, he made himself into a different kind of difference-maker. Even when he made All-NBA, he did the dirty work. Lowry’s disregard for style was a style in itself. His Hall of Fame résumé is a monument to effort and guile.
“His handle and everything is basic,” Williams said. “He’s going to get the job done. The game has shifted a little bit with the step-back, the footwork maneuvers, and Kyle was practicing all that. But he’s doubling down on his style, he’s doubling down on how he plays the game, and you have to appreciate that. That comes from where he’s from, North Philadelphia. It’s a gritty, it’s a grimy area, it’s tough-nosed basketball.”
As Williams told Lowry in 2012, it’s also the type of basketball that makes you beloved in Toronto. Williams said that Lowry exudes heart, and that means everything there. The championship means everything, too.
With Leonard, once again a Raptor, in attendance at Lowry’s press conference on Tuesday, the symbolism was impossible to miss: Before Lowry showed up, Toronto was a place that stars left. It is now a place that stars return to.