Kyle Lowry’s Improbable NBA Journey: From Mr. Stubborn to Mr. Raptor

He didn’t see eye-to-eye with his boss after a franchise-altering trade, but Raptors point guard Kyle Lowry kept his cool, cleared the air and four months later helped lead Toronto to its first NBA title.

This story appears in the July 1, 2019, issue of Sports Illustrated. For more great storytelling and in-depth analysis, subscribe to the magazine—and get up to 94% off the cover price. Click here for more.

The parade buses pulled out of the OVO Center, puttered east down Lakeshore Boulevard, cut north up York Street and turned onto University Avenue before stopping in Nathan Phillips Square, where a horde of red-clad Raptors fans—some of whom had sacked out there in sleeping bags the night before—waited to celebrate the city’s first major sports championship since Joe Carter’s home run delivered a second straight title for the Blue Jays, in 1993.

From a perch atop one bus 33-year-old point guard Kyle Lowry took it all in. He sprayed the crowd with champagne. He hugged Drake. He made small talk with Justin Trudeau. When fans chanted One more year at Kawhi Leonard—the Finals MVP who will become an unrestricted free agent on June 30—Lowry hovered above Leonard, stuck his palm in the air and tweaked the wording: Five more years. He hugged the Larry O’Brien trophy, pressing it to his throwback Damon Stoudamire jersey. Fitting: an homage to the Original Raptor from Mr. Raptor. 

Lowry resists the label. He’s the longest tenured member of the NBA champs—seven years, and counting, during which he made five All-Star teams and led Toronto to five division titles—but he thinks of himself more as a cog in the wheel. Lowry isn’t much for reflection—“I’ll reflect when I retire,” he says—but he appreciates the journey, which began at 20th and Lehigh in North Philadelphia, on the blacktop courts near where Connie Mack Stadium once stood, where the undersized kid with the baggy shorts and oversized T-shirt fired up shots until dinner time—then went back and tossed up a few more. 

The journey took him from Cardinal Dougherty High to Villanova, where his game blossomed after his college career nearly fell apart. Coach Jay Wright remembers his two years with Lowry vividly. “He wanted to do things his way,” says Wright. “The other side of it was you always knew he was intelligent and he had a good heart. Really, it was a strange combination.” Lowry’s insistence on doing things his way had Wright wondering if the four-star recruit was worth the trouble: “It got to the point where I said, ‘If you don’t do it our way, you’ve got to go.’ ” In August, Wright warned Lowry: Don’t ditch freshman orientation. On the first day Lowry was a no-show. Wright was incensed. He intended to toss Lowry off the team. When he tracked Lowry down, he was in the hospital. He had torn his ACL in a summer league game that morning. But he was back on the floor in December and missed only seven games, 

The journey took him to Memphis, where he saw the team draft another point guard, Mike Conley, after his rookie season, then to Houston, where he chafed under the direct, brusque style of coach Kevin McHale. It finally took him to Toronto, where be developed into an All-Star but couldn’t overcome LeBron James in the playoffs, where he bottled up his anger in the aftermath of the Raptors’ trading his best friend, All-Star shooting guard DeMar DeRozan, where he played with amazing fire in the Finals, culminating in a 26-point, 10-assist effort in Game 6 at Oakland, ending the Warriors’ reign. 

“Words can’t describe the feeling,” says Lowry. “Wow. Just f------ wow.”

Andrew D. Bernstein/Getty Images

Last summer Raptors president Masai Ujiri believed his team had plateaued and needed a shakeup. So Ujiri fired Dwane Casey a month-and-a-half before he was named the Coach of the Year, and replaced him with assistant Nick Nurse. Then he flipped DeRozan, center Jakob Poeltl and a first-round pick to the Spurs for Leonard and shooting guard Danny Green, gambling that Leonard—coming off an injury-ravaged season—could push the team to a championship level. Lowry was crushed. 

A hash-it-out meeting between Lowry and Ujiri should have happened last fall. It needed to happen in early February, with the Raptors struggling and the strained relationship between Lowry and Ujiri—who interpreted his star’s put-your-head-down-and-do-your-job mentality as indifference that was poisoning the locker room. “We needed to figure some things out,” Ujiri says. “We needed to communicate. We needed to sit down and talk.”

Lowry is hardheaded. He knows it. He knows where he gets it: His grandmother Shirley Holloway, who raised Lowry with his mother, Marie, was just as stubborn. “About everything,” Lowry recalls. Don’t walk down the stairs like that. Don’t cook grits like that. On Sundays, don’t think about coming near the kitchen until she was done cleaning. “Like, ‘Everybody get out of my goddam way or I ain’t cooking breakfast,’ ” Lowry says. “You don’t get breakfast when she’s cleaning. How I am, that’s straight from grandma.”

That streak cut both ways. It earned Lowry a reputation as hard to handle. He didn’t think he deserved it with the Grizzlies, who drafted him in the first round in 2006 only to give up on him midway through his third season. “I had bad coaches,” says Lowry. He definitely deserved it with the Rockets. Lowry spent two and a half seasons playing for Rick Adelman, connecting with the coach’s laid-back approach. After the 2010–11 season, Houston replaced Adelman with McHale, whom Lowry, then 25, clashed with immediately. “You have to earn [Lowry’s] trust,” says Wright. “He’s not giving that away easily.” After one season together, Lowry requested a trade. “I didn’t buy in,” says Lowry. “I have apologized to Kevin. I didn’t know he was trying to coach me. At the time, I didn’t understand it.”

That stubbornness, though, fuels Lowry. After being traded to Toronto, a rival executive (Lowry declines to name him) told him he should prepare for life as a backup. Lowry has played 497 games for the Raptors—and started 481. A former teammate (“Jared Jeffries,” says Lowry. “Yeah, you call him out”) once told Lowry he would never make more than $5 million per year. In 2017, Lowry signed a three-year, $100 million deal. 

A tense meeting with Ujiri wouldn’t be a first, either. Ujiri didn’t trade for Lowry. He was hired in 2013, a year after the Raptors acquired Lowry from Houston for a first-round pick and little-used swingman Gary Forbes. Ujiri loved Lowry’s talent. His fearlessness. His ferocity. He hated his body language and his defiant attitude. Before training camp that fall, Ujiri called Lowry into his office. He challenged him. He said Lowry could be a $4 million per year player or a $12 million per year man. Lowry heard him. He responded with a career-best season, improving his scoring average from 11.6 points to 17.9 and propelling Toronto into the playoffs. 

So here the two were again, days before the February trade deadline, squaring off once more. Ujiri admits he didn’t realize how hard the DeRozan trade would hit Lowry. But with the playoffs approaching, the issues between player and president needed to be dealt with. “It was, ‘Let’s have a conversation and see where we are,’ ” Lowry says. “We weren’t as cohesive a team as we could have been. We could have, we should have been at that time, and we weren’t there. Things were just building up.”

Both declined to discuss the specifics of what was said. “It was a tough meeting,” says Ujiri. “We both expressed how we felt. And then we started to reason.” Lowry told Ujiri he wanted to be there, that he believed in this team. When DeRozan was traded, Wright told him: Be professional. Hold it in. Chauncey Billups, a longtime mentor, said the same. “That’s the thing about being a man and being a professional, that you go in here and you do your job,” says Lowry. “You don’t pout. I didn’t pout, I just went out there and went to work.”

Ujiri needed to hear more. Lowry needed to say more. In the two-hour meeting, the two aired it out. “We needed to voice our opinions to each other, face-to-face,” says Lowry. “My emotional side as a friend—yes, I definitely was upset [about the trade]. My best friend is upset, so I’m upset. But the business side of it is like, ‘Listen, you’re getting the top one or two basketball players in the world in Kawhi Leonard. I knew how talented he is.' We had to make sure we were on the same page. And we were.”

That meeting, says Ujiri, “was a turning point.” The Raptors went 8–1 in February. They finished the season with 58 wins, second only to the Bucks’ 60. Lowry’s confidence in the team swelled. After dropping the first game of the opening round to the Magic, Toronto had a team meeting. Lowry approached Ujiri, declaring that the Raptors would win four straight. They did. After losing Game 2 of the Finals, Lowry called Wright and said, We’re winning this series.

“He just loves having his back against the wall,” says Wright. “At Villanova, every time we went into a road gym as a staff we would say, ‘Thank God we got Kyle Lowry.’ Because we knew he loved to play on the road. He loved everybody being against him, and we all knew it.”

In Oakland, when the buzzer sounded after the clincher, Lowry spotted Ujiri trying to get onto the Oracle Arena floor. A police deputy blocked him, telling him he didn’t have the proper credentials. (The officer alleged Ujiri struck him, which he denies.) Lowry shouted at Ujiri, then pulled him past security. Ujiri had just constructed the first championship team in Raptors history. And the first player he hugged was Kyle Lowry.

Ron Turenne/Getty Images

Champagne-soaked, Lowry sat in his locker inside Oracle Arena after Game 6 and pulled out his cell phone. He scrolled through his messages. There were 650. Friends. Family. Ex-teammates. Ex-coaches. Adelman offered his congratulations. “Anyone that knows Rick [knows] that’s something,” says Lowry, laughing. “I said, ‘Oh s---, I’m definitely responding to this one. And I’m saving this number.' ”

Lowry replied to nearly all of them. He started as he was sitting in his locker, and he finished just after five in the morning. “I always do,” says Lowry. “People that text you are thinking about you, so why not reach out to them and say ‘thank you’ or ‘I appreciate it’?”

In the hallway his kids, Karter, seven, and Kameron, three, waited. A championship means everything to Lowry. Sharing it with his sons means more. He grew up with an absentee father and vowed his kids never would. Kameron, says Lowry, isn’t old enough to fully grasp what this season has been like. “He just likes to play in the confetti,” says Lowry. Karter, however, is. As his teammates celebrated the series clincher, Lowry pulled Karter close and told him, “We did it.”

And now Lowry wants more. “My goal is to keep winning championships,” says Lowry. “Get another, then another. I know I can play this game at a high level for a few more years. I want to continue to be a winner.”

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Enter Leonard, whose free agency will dictate the future of the franchise. Lowry learned a lot from Leonard—most importantly, the value of staying even-keeled. “Never get up, never get down,” says Lowry. “That’s one thing I’m going to continue with for the rest of my career.” Lowry has no problem deferring to Leonard. Never did. When Leonard arrived for training camp, Lowry told him the Raptors were his team now. As 25-year-old forward Pascal Siakam began to expand his game, Lowry told him it was his time, too. “For me, it was about making my teammates comfortable,” says Lowry. “That’s all that mattered.”

No one, including Lowry, has any idea what Leonard is going to do. The Raptors will offer him a five-year, $190 million contract next week, the richest deal he can get. They can also offer a more flexible, short-term deal. But the Clippers have shadow-recruited Leonard all season, and the California native could be tempted to return home. 

“I want him to stay,” says Lowry. “I’d love him to stay. But he’s my friend. And I always say this in this business, you don’t have that much choice in happiness sometimes. You have to make yourself happy. You have to be able to wake up every day and be happy with what your decision in life is, and that’s why I never recruit. I never say like, ‘Listen, yeah, I want you back. Come on back. Let’s continue to be teammates. But if you choose to do something different, I’ll support you.’ Free agency is where you make a decision. And if he chooses to do whatever he chooses to do, I swear I’d be happy for him. I have no idea what he’s going to do. All I know is that he’s happy right now, and he’s a fun guy.”

With Leonard, the Raptors will be favorites to repeat. Without him, they could be in rebuilding mode. Lowry could be traded. The team could be ripped apart. But they will always have that title. And the kid from North Philly will forever be part of Canadian sports lore. During the Finals, a kid reporter asked Lowry what it felt like to be an icon. Lowry, briefly, was speechless.

“I truly just want to be able to have people look at me as a guy that holds himself to a high standard,” says Lowry. “I just want to be a guy that people could say, ‘Man, that guy was a real good guy. He was a legit man. He took all the punches, he took all the criticism. He took everything, and he stood tall 10 toes down.’ ”