Kyle Lowry’s Path to Toronto Was Unexpected, but Meant to Be

The night was a walk down memory lane from the moment he set foot in Scotiabank. But the buildup of his potential last game in the city he called home for nine seasons almost didn’t happen in the first place.  

How Kyle Lowry Became a Raptor

When a 26-year-old Kyle Lowry landed in a new country, he couldn’t have imagined what Canada would mean to him. He’d spent two and a half years in Memphis coming off the bench and just over three seasons in Houston.  

Though he continued to develop his skills to blossom into a starter in Houston, Lowry only made the playoffs once with them — in 2009. Rumors of dissension between him and then-coach of the Rockets, Kevin McHale, coupled with Goran Dragic stepping up in Lowry’s injury absences, resulted in the team moving on from him. 

Meanwhile, in Toronto, former GM Bryan Colangelo was attempting to recruit Hall of Famer Steve Nash. After Nash chose to team up with Kobe Bryant in Los Angeles, the Raptors sought out Lowry.

Lowry was acquired by the Raptors in July of 2012. 

Team Uncertainties

The season after Lowry was dealt to Toronto, 2013-2014, the team started 6-12. Freshly hired Team President Masai Ujiri felt the team needed a rebuild and was looking to make several moves. Ujiri hoped Lowry, along with Rudy Gay and DeMar DeRozan, could form a star trio to lead the Raptors to relevance; however, they had struggled. 

Rudy Gay was subsequently traded that December, with Lowry slated to be next. Ujiri was reportedly in talks with several teams to trade his point guard, including the Lakers, Heat, and Knicks. As talks escalated with New York, many began assuming it was a done deal – even Lowry himself.

“I didn’t think I was getting traded anywhere besides the Knicks,” Lowry said. “I honestly thought that was going to happen. I had two duffle bags ready to go.”

Knicks owner James Dolan ultimately backed out of the deal at the last minute, leaving the Raptors stuck with Lowry. The story goes that Dolan grew hesitant to engage in business with Ujiri. Dolan had been scolded in the past for making deals with Ujiri that ended poorly for the Knicks. Additionally, the Knicks’ owner refused to send the players needed to make the deal work. 

Head coach at the time, Dwyane Casey, said: “Once he saw that he wasn’t going to be traded, he took it as a personal challenge as far as the team and everything to make sure he put it on his back.”

That he did. Lowry began to grow his chemistry with DeRozan, eventually becoming All-Star backcourt mates. The two turned their team’s season around that year, clinching a postseason berth and taking the Kevin Garnett-led Nets to a grueling seven-game series. 

An Unlikely Friendship

The relationships Lowry formed along his journey left a lasting impression on those around him. Though Lowry is now playing for the City of Brotherly Love, he experienced that same love with DeRozan during their time together. 

Initially, however, Lowry and DeRozan’s relationship was rocky when they first joined forces. As DeRozan described in his memoir, “Above the Noise: My Story of Chasing Calm,” the two weren’t immediately best friends. 

“He’d come and go and never really seemed a part of the team,” DeRozan recalled of his first impression of Lowry. “He walked around the facility in a hoodie with the hood pulled up over his head and always seemed short-tempered with everybody,” (pg. 104). 

Lowry was a vocal leader unafraid to express how he felt; DeRozan was reserved and kept to himself. 

DeRozan grew to understand that he and Lowry had much more in common than either thought; they just went about their business differently. Both came from struggling households in rough neighborhoods. Both fought against becoming a product of their environment to create a better life for themselves.

The turning point in their relationship came after Game 7 of the 2014 first-round playoff series against the Nets. The game came down to the wire, and the Raptors had the ball with 6.2 seconds and a chance to take the lead. Lowry had a potential game-winner blocked by Paul Pierce, resulting in a devastating one-point loss for the Raptors. 

In that moment, DeRozan reached down to console Lowry, who had dropped to the floor in pain-staking disbelief. 

“I don’t care if you made that shot or if you missed,” DeRozan reassured, “I’m riding with you no matter what,” (pg. 113). 

More Than Just a Game

Their connection strengthened throughout the years, with Kyle Lowry’s loyalty and support providing comfort for DeRozan, especially as he was battling personal issues behind the scenes. 

Once DeRozan’s dad fell ill during the 2017-18 season, it was Lowry who became his confidant. Their lockers were adjacent to each other, and only he knew the true extent of his condition.  

“I felt I could trust Kyle with anything,” DeRozan said (pg. 125). 

“When I was going through my worst, he would lean into my locker stall before games, when the rest of our teammates were talking among themselves, and look me in the eyes, ‘All right, D, let’s go to our happy place’,” (pg. 126).  

“When games were over, he’d put an arm around me on our way back to the locker room and say, ‘Now back to reality. You got this’,” (pg. 126).

His pregame and postgame talks with Lowry allowed him to open up about his feelings — something that he’d spent decades afraid to do. For DeRozan, Lowry was a safe space. He allowed him to be vulnerable and tear down the facade that so many professional athletes hide behind.  

Lowry Set the Foundation in Toronto

The end of Lowry’s time with the Raptors in 2021 was an amicable parting of ways. The team was revamping and going younger. An aging Lowry was nearing the end of his prime, looking for a last opportunity to win another title. 

His stops in Miami, Philadelphia, and Toronto saw him become a mentor to the teams’ young players.

His young protege in Toronto, Fred VanVleet, calls Lowry “a big brother” for helping him in basketball and in life. VanVleet spent years soaking up knowledge from his vet as he emerged from an undrafted guard to an NBA starter.

Lowry’s work ethic set the standard for his up-and-coming teammates. They were always paying attention to how he went about his business. 

“I remember in training camp, I would show up two hours early to practice, and he would already be there, done with his workout,” VanVleet described of Lowry’s routine. 

“I learned a lot from Kyle. Not really about my game, but how to move — business things, family things, how to work out, your routine, how to recover.”

To this day, the two stay in touch, texting each other throughout the week. 

Kyle Lowry’s Role as a Mentor

Kyle Lowry brought those same leadership qualities with him to Philadelphia. Tyrese Maxey specifically has praised him for always being in his corner. Like with Lowry’s Raptors teammates, his support and care extend far beyond basketball for Maxey. Despite Maxey facing off against the 39-year-old just once while he was a Raptor, he is fully aware of the love Toronto has for him.

“He’s a legend. He’s legendary,” Maxey said. “What he’s done for this organization, franchise, whole country, is bigger than basketball.”

When asked what he learned from Lowry, he simply responded: “Literally everything. I take so much from Kyle every single day.”

The bond the two have is why he, along with the rest of the 76ers’ players, focused on putting the game away as early as possible.

Lowry hasn’t confirmed whether or not this season will be his last, but the end is getting closer.

Just two months shy of his 40th birthday, the Philadelphia native has seen a drastic dip in playing time over the last two seasons. Lowry has logged minutes in only 41 games since the beginning of the 2024-25 season. His body isn’t holding up as it used to.

The best shot Lowry had at seeing the floor was if the game was put away, which Maxey tried hard to do. He wanted his mentor to get one last ovation (possibly) from the fans who watched him grow up. The fans that were there through the highs and lows, and witnessed him hoist the Larry O’Brien trophy. 

Maxey’s bloom into stardom has meant that Lowry can take a backseat, leaning into more of a leadership role. Still, if Maxey ever needs anything, he knows Lowry is there for him.

Forging a Lasting Legacy

At this point, the legacy of Kyle Lowry up North is one that is familiar. He is a multi-time All-Star, Olympic Gold Medalist, and NBA Champion. But what means the most to Raptors fans is that he chose to stay when the going got tough. Lowry may not have been drafted to the Raptors, but it almost feels like he was. He loved Toronto like it was his home.

 Because of the deep ties he has with the city, he intends on retiring a Raptor. He has stated on numerous occasions his plan to sign a one-day contract with the team before leaving basketball.

Fans had seen the same story too many times. They’d watched players like Vince Carter, Tracy McGrady, and Chris Bosh walk out the door, leaving nothing but broken hope to a fanbase aching to have a player to call theirs. Someone who was along for the ups and downs, and was as committed to them as they were committed to him. They finally got that player.

What they didn’t know was that he would be one narrowly missed trade away from never becoming theirs in the first place.