Believe it or not, Kyle Lowry is gearing up for his eighth season with the Toronto Raptors. It has been a rollercoaster of a ride, with the peak coming in April when he helped bring home the franchise’s first Larry O'Brien Trophy.

Lowry has become an iconic figure in the team’s history. In light of the news Monday that he’s reached a one-year contract extension with the team, let’s take a look back at Lowry’s time with the Raptors and how we got to this moment.


The Arrival:

On July 11, 2012 the Toronto Raptors sent Gary Forbes and a 2013 first-round pick to the Houston Rockets for Lowry. The move saw the Raptors land a 25-year-old point guard who had just averaged a then career-high 14.3 points per game in 47 games.

His first season in Toronto was a rough one; Lowry played in 68 games, starting 52 of those but scored just 11.6 points per game, his lowest total in his last three seasons.


The Trade That Never Was:

Less than a year after being traded to Toronto, it looked like Lowry was once again going to be on the move. Things weren’t going the way general manager Masai Ujiri had planned, and it appeared he was ready for a full-blown rebuild. On Dec. 9 2013, Rudy Gay was moved out of town and Lowry seemed destined to follow him.

Lowry was going to be a New York Knick, in a deal where the Raptors would have received Metta World Peace, Iman Shumpert and a future first-round draft pick.

But Knicks owner James Dolan stepped in and called the deal off. Dolan had been burned by Ujiri before when he was in Denver and traded Carmelo Anthony to Dolan’s Knicks for a number of valuable assets.

The trade was off, Lowry remained a Raptor, and the team went on to make the playoffs.


Playoff heartbreak:

With Lowry and DeMar DeRozan leading the charge, the Raptors were back in the playoffs for the first time since the 2007-08 season. Toronto faced a veteran-led Brooklyn Nets team and came up just short in Game 7 when Lowry had his game-winning layup attempt blocked.


The Contract:

Just months after almost trading him away, the Raptors and Lowry agreed to a $48-million contract that would keep him in Toronto for four years. The deal cemented the fact that Lowry was the point guard of the future in Toronto, giving him security and a new home in Canada.

His first season with the new contract was a good one, at 28-years-old Lowry made his first all-star team, scoring 18.6 points, 7.1 assists and adding 4.9 rebounds per game.

That season was the first of five straight All-Star Game appearances as Lowry finally had a seat at the table with the games top-tier point guards. 


More Playoff heartbreak:

The Raptors looked better than ever going into the 2015 playoffs, the Lowry and DeRozan-led Raps had a date with the Washington Wizards. But their 49-33 regular season record did them no good and they were swept in the first round.

The breakthrough finally came in the 2016 postseason, as Lowry and the Raptors made their first conference finals in team history, losing in six games to the LeBron James-led Cleveland Cavaliers. Lowry shined that spring, averaging 19.1 points per game in the playoffs (a number he has not surpassed since). 

Unfortunately, the 2017 and 2018 playoffs were the same story: win the opening round in six games and the get swept in the second round by the Cavs. 

Something wasn’t working. The team had plenty of regular season success, but couldn’t get over the hump.


The DeRozan trade / Issue with management:

Lowry and DeRozan had become one of the tightest duos in the NBA, and had a chemistry and bond that seemed inseparable. And then, at 2:30 a.m. on a July morning, Lowry got a phone call from DeMar saying that he had been traded. The return for DeRozan was massive, landing Kawhi Leonard and Danny Green, but Lowry wasn’t happy.

In an interview with ESPN’s Rachel Nichols, Lowry said he “felt betrayed because [DeRozan] felt betrayed.”

When asked in that same interview about his relationship with Ujiri he said, “He’s the president of basketball operations, and that’s it,” he added. “For me, I come out here and do my job.”



After all of the heartbreak and all of the ups and downs, Lowry, the Raptors, and their new running mate Kawhi Leonard broke through in 2019.

At the age of 32, 12-years after making his NBA debut with the Memphis Grizzlies, Lowry became an NBA champion. The dramatic run saw the team go seven games against the Philadelphia 76ers in the second round and six games against the Milwaukee Bucks in the Eastern Conference finals, before beating the defending champion Golden State Warriors in six games.

When the lights were the brightest Lowry didn’t miss a beat. He and Pascal Siakam led all Raptors with 26 points in the championship-clinching game. It was Lowry who set the tone that night, opening the game with his own 11-2 run and picking up three assists in the first quarter.