The 15 Greatest Toronto Raptors of All Time, Ranked

Image via Complex Original/Kagan McLeod

Traded from the New York Knicks to Toronto in June of 1998, a 35-year-old Charles Oakley provided the Raptors with a physical inside presence and veteran leadership that was invaluable to a team coming off its worst season in franchise history, winning just 16 games in 1997-98. But more important than that, Oakley brought a sense of legitimacy to the struggling expansion franchise, lending a hand in turning around its image as he helped make the Raptors winners that demanded the rest of the league’s respect. 

After all, Oakley was one of the greatest (and toughest) players on two of the greatest and most important teams in the league throughout the 1980s and ’90s, playing with Michael Jordan’s Bulls and then Patrick Ewing’s Knicks, going to the playoffs in each of his first 13 NBA seasons. He simply knew how to win and how to hold his teammates (and opponents) accountable, which was why the Raptors traded a promising young player in former No. 2 overall pick Marcus Camby for a past-his-prime Oakley and didn’t look back, with Oakley becoming the missing piece on a promising young team beside cousins Tracy McGrady and Vince Carter. 

Oakley played three seasons in Toronto between 1998 and 2001, appearing in 208 of a possible 214 games as a Raptor, starting in all but one of them. Oakley held his young stars accountable and made sure that no one on the other teams were going to mess with them, acting as an enforcer in a much more physical NBA that let him get away with a lot more than he would have gotten away with today. He was a unique character who brought with him winning habits, ultimately helping the Raptors reach their first playoff appearance in 2000 and then to their first playoff series win in 2001. —Oren Weisfeld

The Toronto Raptors have had their fair share of international players over the years, but none were more beloved by teammates and fans during their time in Toronto than Jose Calderon.

Calderon, who left his family as a teenager to play basketball professionally in Barcelona, Spain, signed with the Raptors in 2005 as an undrafted free agent. The 24-year-old went on to become one of the best point guards to ever don a Raptors uniform. The Spainiard suited up in 525 games over eight seasons with the Raptors, finishing in the top-10 in games (525), minutes (14,909), and field goals made (2,023). But Calderon was a pure, pass-first point guard, bringing the best aspects of European basketball to the Raptors and the NBA, including his flashy playmaking and feisty attitude. In fact, Calderon was the franchise leader in assists (3,770) before Lowry (4,277) passed him in 2020, and he still ranks third in assists per game (7.2) and second in assist percentage (39.9). 

Ironically, Calderon entered the league as a poor three-point shooter, but as the NBA evolved towards the pace and space game that it is today, so did Calderon. After shooting just 24.8 percent from beyond the arc in his first two seasons, including 7-for-43 as a rookie, Calderon went on to become one of the most efficient three-point shooters in Raptors history, ending his career as a 40.7 percent three-point shooter. His improved outside shot was one of the biggest reasons why Calderon was able to stay in the league into his late thirties, ultimately playing for seven franchises over the course of 14 seasons.

But it was in Toronto that Calderon left his biggest mark, beating out several players for the starting point guard gigs throughout the years while still being considered one of the greatest teammates in Raptors history. Calderon played for four different coaches in Toronto and was here for the good (2006-2008) and the bad (2008-2013), ultimately passing the torch to Lowry and the We The North era of Raptors basketball. —Oren Weisfeld

Picture it: You’re downtown Toronto in early November 2012, maybe you’re at the Eaton Centre; there was still a Sears around there then so maybe you’re buying some new pillows. All of a sudden down Yonge Street comes this horde of people, dressed like zombies. You know it’s just a joke thing, but a part of you still doesn’t feel all that great watching a bunch of grown adults drag their feet as if their feet are broken, with blood and guts smeared across their face. But then, poking out of the crowd is a familiar face. It’s a face with a lot of grotesque makeup on but still, you’d know that face anywhere. It’s Amir Johnson. You feel instantly at ease and loosen up your grip on your pillows, gone flat in your hands.

Johnson was important to the Raptors for a lot of reasons that are lost now to the new heights the team arrived at once he left. Kind of like an archeological dig, buried in the sands of time. But the thing he came to be loved best for is how much he genuinely loved being in Toronto. After a long bout of players packing up for sunnier places, or straight up no-shows, it was a genuine joy to have a guy who played his heart out on the floor, did all the extras right and with care, and still made it feel like there was no place, no team, he’d rather be on. And those were lean years where the only plan was the postseason, to just make it there. Amir Johnson helped get us there for a long time. —Katie Heindl

Jonas Valanciunas, Lithuanian Lightning, or simply JV; whatever you want to call him, Valanciunas goes down as one of the greatest centers to ever play for the Raptors. Even though his game would have been better suited to the NBA of the 1990s than the one he actually entered, JV was a skilled 7-footer who became a beloved personality in Toronto for his feisty personality on the court, his quirkiness off of it, and his willingness to do whatever was asked of him and to take it in stride. 

The fifth overall pick in the 2011 NBA Draft, Valanciunas spent a year in Lithuania before making his way over to Toronto, where he had to get acclimated to the culture and language while learning the drastically different NBA game. In fact, Valanciunas came into the league at a very weird time for big men, just as it was beginning to transition towards a more perimeter-oriented game with more outside shooting and a faster pace. That’s why the Raptors asked JV to perform any number of roles during his seven seasons in Toronto, oscillating from putting on weight to taking it off; from emphasizing strength to emphasizing mobility; from playing with his back to the basket to shooting the three. 

But Valanciunas took it all in stride and succeeded in almost every role asked of him, always doing the dirty work of screen-setting and rebounding, helping the We The North era Raptors have the most successful run in franchise history. JV continued to be a good teammate and to alter his game to the Raptors’ needs until the very end, when was ultimately traded to the Memphis Grizzlies in return for Marc Gasol. Even then, JV never soured, returning to Toronto as a spectator as he supported his old team in the playoffs, watching them bring Toronto its first NBA championship that same year. —Oren Weisfeld

Look, what Marc Gasol did to Joel Embiid in the 2019 playoffs is reason enough for him to be on this list, despite his comparatively brief tenure to the majority of the names here. Gasol became a vortex, a vacuum, and a Great Wall to Embiid’s in-game capabilities and off-court psyche. That Sixers series was a gauntlet—just look at the knife’s edge on which it ended—and the Raptors don’t make it out as the winners without the calm, cool, and savant status of Gasol’s defensive mind. What’s more, his stoicism was a ballast when the team needed it and his occasional bursts of passion, either in the form of a perfectly timed hard stop or just throwing his arms up and roaring, were perfect emotional counterweights to Kawhi Leonard’s robotic calm.

Kyle Lowry found a perfect outlet in him, Fred VanVleet and Pascal Siakam got some much needed space, and Leonard gained welcome company with another elite defender, while the Raptors got all the rim protection and rebounding they could handle—crucial in the closer games that came in each of Toronto’s playoff matchups. And Gasol was no slouch in the regular season, digging in as soon as he got off the plane from Memphis and carrying the championship shine into the season that followed despite injuries and a pandemic.

Gasol was a crucial part of the best Raptors team of all time, a roster of rare balance that had every player working in perfect tandem. That’s legacy stuff, even if it only was two seasons. —Katie Heindl

Fred VanVleet might not have even made this list one year ago. And yet, out of all the players on this list, VanVleet has the most potential of continuing his steady rise towards the top in the years to come. Still, it’s worth celebrating what VanVleet has already brought to the franchise, because his is one of the greatest success stories not just in Raptors history, but in the history of professional sports. 

VanVleet went undrafted out of Wichita State in 2016 and coined the phrase “Bet on Yourself,” determining his own fate as he accepted an invitation to Raptors’ training camp that summer. VanVleet won a roster spot, played with the Raptors 905 of the G League, and then won minutes on the big club when Delon Wright went down with an injury, taking a little bit of luck and a whole lot of hard work to cement himself as a key part of the Raptors “bench mob” by his second season. 

Since then, VanVleet has, well, how do I put this: been freaking awesome! The 27-year-old Rockford, Illinois native has become one of the best three-point shooters in the NBA, a smart, hard-nosed defender with a knack of poking the ball loose, a heady playmaker who is still improving and, in the mould of his mentor Lowry, a winning player who consistently makes his team better despite being barely six feet tall. VanVleet also hit some of the biggest shots in franchise history during the 2019 title run, seemingly refusing to miss a shot after the birth of his son, Fred Jr., midway through the playoffs. 

It’s truly remarkable how VanVleet has beaten the odds at every stage in his career to be what he is today: the on- and off-court leader of the Raptors and their best player this season, averaging 21.7 points, 4.7 rebounds, and 7.0 assists while leading the league in minutes. 

Steady Freddy. Freddy All-Star. Freddy Vandalay. Whatever you want to call him, VanVleet has only just begun his unlikely rise towards the top of the NBA’s totem pole. And, more importantly for the purposes of this exercise, the list of Toronto Raptors all-time greats. —Oren Weisfeld

Had the Raptors not selected Damon Stoudamire with the seventh overall pick in the 1995 NBA Draft to commence their inaugural season, the Raptors might not be the Raptors anymore. Or, at the very least, they might not be the Toronto Raptors anymore. If not for Stoudamire, the Raptors could very well have folded like their Canadian counterpart Vancouver Grizzlies did in 2001.

After all, the odds are against you as an expansion franchise, especially one north of the border playing in a baseball stadium for their first few years. So, getting the first draft pick right tends to be very important. But when Raptors general manager and Hall of Fame point guard Isiah Thomas selected the 5-foot-10 Stoudamire out of the University of Arizona in the 1995 NBA Draft—which happened to be held in Toronto’s Skydome— he boos came raining down from the 20,000 Canadian fans in attendance. To which Stoudamire confidently responded: “Wait until these fans watch me play. Trust me, they won’t boo me anymore.”

Stoudamire, or Mighty Mouse, was right. The hard-nosed point guard endeared himself to Raptors fans immediately with his edgy demeanor and flashy game. He could shoot, pass, drive; you name it. And he could do it immediately, winning Rookie of the Year in his and the franchise’s first season. And it didn’t matter who he was going against, either. In fact, Stoudamire cemented his rookie of the year campaign with a brilliant 30-point, 11 assist performance at the Skydome against Michael Jordan’s Chicago Bulls during their historic 72-10 season. 

While Stoudamire’s Raptors tenure ended shorter that it should have due to a front office dispute forcing general manager and mentor Thomas out of town—with Stoudamire asking for a trade shortly afterwards—he will always be remembered for the showman that he was and for keeping the Raptors afloat (and alive) at a time they were having trouble simply keeping other players in Canada. Stoudamire breathed life into a franchise that was desperately in need of it, and every Raptor that came after him has Mighty Mouse to thank for putting the team on his back during the franchise’s early years. —Oren Weisfeld

Chris Bosh was the highest pick the Raptors had in close to a decade and he arrived to a powerhouse of a team that was, nevertheless, an offensive nightmare (not in its own favour). Vince Carter and Bosh would only play Bosh’s rookie season together, but Bosh saw the team’s void for a star and stepped into it at just 20 years old. For the next six seasons Bosh was a powerhouse, averaging between 22-24 points per game and shooting 48 percent or better. Bosh got stuck in the quagmire that followed Carter’s exit and every team the front office attempted to build around their best player didn’t quite work, but he brought the Raptors to two postseason appearances and still leads the franchise in offensive, defensive and total rebounds, and blocks. —Katie Heindl

Pascal Siakam has come to embody the best and the worst of the Raptors as a franchise, unfairly or not. It’s rare for any athlete to have such a meteoric rise, rarer still for a basketball player to hit the kind of heights he has after picking up a ball for the first time at the age of 18. That he’s already made it so high up on this list, in such a short amount of time, is evidence itself of his incredible come up. Statistically, he’s only ever gotten better season over season—but symbolically he is all raw, unbridled hope and promise as much as he’s the counter of those same feelings: doubt and difficulty. Heights come with plateaus, but the timing of Siakam into Toronto’s grand scheme as a team has never aligned with patience because the teams he was on were always, until a couple seasons ago, winning.

To put Siakam on a list like this is to embrace the duality that he represents. That his field goal percentage has never dipped below 45 but he can still be harangued as a hopeless shooter, or that he was part of the same gilded, gritty 905 team that won the G League championship and more or less immediately went on to win an NBA title, and now leads the franchise as its preeminent star are perfect encapsulations of that endlessly frustrating, forever joyful bilaterality. The crux of it is that the discourse will always continue, because fans see in Siakam the good and the overblown, the bad and the actually fine, and want to believe there will always be more and it will always be better when the reality is, and has always been, the Siakam they are seeing right now is that best version. So please, enjoy it. —Katie Heindl

Out of all the players on this list, the seasonal sample size is lowest for Kawhi Leonard, but he’s still technically the best player the Raptors have ever had. Six of the franchise’s 13 highest scoring playoff games came from him and he’s the only Raptor to ever make an NBA All-Defensive team, he ranks right after Lowry and DeMar DeRozan in all-time postseason scoring after just 24 playoff games. Leonard was a postseason pro, and he taught his teammates what it was to show no mercy, or emote much of anything, until the job was done.

Besides the numbers and ultimate, pretty glorious outcome, there’s something strictly aspirational about Leonard landing in Toronto. He was the calibre of player fans had long been told would never, ever end up in Toronto (even when the trade had happened, that was still the rhetoric) because as a city and a club, it wasn’t big enough. Whether it was a real or psychic barrier, Leonard in a Raptors jersey shattered it. What’s more, Leonard came to trust the franchise as a result of the care its medical and training staff took with him—no small feat after his relationship with the Spurs deteriorated so completely. The window was always going to be small—that was the bargain Masai Ujiri struck in trading away half the team’s heart for its best hope of a title—but Leonard gave Raptors fans a hell of a view. He even laughed, a lot! —Katie Heindl

How do you break a generation’s heart? Ask Vince Carter. Carter who put Toronto on the map for the first time with Vinsanity, with the best NBA Dunk Contest there ever was, who had the face for SLAM and SI covers but the game to back it up, and who still leads the franchise in points per game and overall efficiency. Carter could do it all, did it all in Toronto for a while, and then just… quit. When he walked, it would be the catalyst for a psychological weight most long-time Raptors fans didn’t shake until the team won the title and for that kind of cruel impact alone, Carter’s career in Toronto was franchise shaping.

Even with the eventual reconciliation, Toronto doesn’t become the gritty, do-whatever-it-takes-to-win team it did under DeRozan and Lowry—teams without baggage don’t play that way. One of the most visceral feelings I’ve ever had at a basketball game was when Carter came to town with the Grizzlies and about two seconds into the familiar, requisite booing, the entire arena changed its mind and started to cheer. It was a weight being lifted, a wound being sewn up; Carter cried and a very long and difficult chapter closed. —Katie Heindl

This is difficult because when tasked to write a blurb about Kyle Lowry, the greatest Raptor of all time on this list, in real life, and in the hearts of hundreds of thousands of people, the task of distillation is impossible. So let’s be loose.

Because that’s what Lowry did for the Raptors. When he and DeMar DeRozan decided to dig in for Toronto, to look beyond where the franchise ever had before with its aspirations, they took a strung-out, cobbled together, dejected group and pushed it as hard as they could. Lowry whipped everything, everyone, into shape, including himself. He took his wide scope, cerebral style of play, and drilled it into his teammates until it trickled down into the G League and the next generation of Pascal Siakam and Fred VanVleet, and was basically atmospheric for Serge Ibaka, Marc Gasol and later, Kawhi Leonard. They all felt it, like weather. Toronto was always a catch-up team, a come-behind group of gritty, dogged, not especially beautiful basketball players, and Lowry was in that too but after, after all that, there was a lightness. When you know the game as well as Lowry does there’s never any reason to panic. Raptors basketball, for the first time in its still-short history, became easy. A pleasure. —Katie Heindl