Illustration by @drakecereal
Illustration by @drakecereal
As the Toronto Raptors celebrate their 25th anniversary, we’re counting down the 25 best players in team history. But who will reign supreme?

The great Toronto Raptors experiment began on Nov. 3, 1995, in front of 33,306 fans at the then SkyDome. And for a long while after it seemed to have gone irreparably awry. Through 18 years of existence, the franchise had a .406 win percentage and a grand total of: four playoff appearances, one playoff series victory, and one Atlantic Division title.

But the last six years have been awful kind. Six more playoff appearances, eight playoff series victories, five Atlantic Division titles … and one NBA championship.

And as if the team didn’t have enough to celebrate right now, they are also recognizing their 25th season in the NBA with a series of “95 Rewind” nights. In honour of the first of those dates Tuesday, we’re taking a look back ourselves — by breaking down the 25 greatest players in team history.

For this definitive list, we sought the help of 11 Sportsnet insiders — Donnovan Bennett, Ashley Docking, Brad Fay, Michael Grange, Paul Jones, Faizal Khamisa, Steven Loung, Arash Madani, Danielle Michaud, Eric Smith and Dave Zarum — and asked each to create a personal ranking based on two criteria: individual play as a member of the Raptors and impact on the franchise. Then we amalgamated them for the final rank.

Read on for the results. And try not to get misty when you think of just how far this team has come.

#25. T.J. Ford

Ford came to the Raptors looking for a fresh start after a spinal cord injury robbed him of an entire season with the Milwaukee Bucks and the emergence of Mo Williams made him expendable. He found it and was very effective for a time, helping the Raptors to their first-ever Atlantic Division title in 2006–07. However, Ford still couldn’t shake the injury bug, and the strong play of backup Jose Calderon ultimately made him expendable again as he was traded to Indiana as part of the Jermaine O’Neal deal two seasons after arriving in Toronto. — Steven Loung

#24. Jerome Williams

A career role player who averaged 7.9 points and 7.0 rebounds in 180 games with Toronto, fans loved Williams’s manic energy. Something was going to happen — good or bad — when he entered the game. It didn’t hurt that Williams was more excited to be a Raptor than anyone before him. He drove through the night from Detroit when Toronto acquired him during the 2000–01 season, and made being a Raptor seem refreshingly fun. — Michael Grange

23. Lou Williams

Being the best sixth man of a generation is a dubious title — you’re good enough to log heavy, productive minutes off the bench, but still not relied upon as a starter. Yet it doesn’t seem to bother the smooth, deceptive Williams, who won the first of his three Sixth Man of the Year awards during his lone season with the Raptors in 2014–15. Immortalized for the general public in Drake’s “6 Man,” Williams averaged Toronto’s third-most field goal attempts that season despite playing the seventh-most minutes. — Arden Zwelling

“The Raptors don’t get out of the second round and on the road to history without him.”

#22. Jalen Rose

Even though the former member of the Fab Five didn’t leave as large an imprint in Toronto as he did at Michigan, his time as a Raptor was solid, averaging 16.7 points per game during a time when the team was in turmoil. Rose’s best quality was his candid nature with the media — unsurprising in retrospect as he’s moved on to a successful broadcasting career. Unlike some other former players turned media members, he’s spoken fondly about his time in the country and playing for the organization. His impact as a team ambassador may eclipse his impact on the court. — Donnovan Bennett

#21. Marc Gasol

It was no coincidence Toronto led the NBA in three-point shooting after his arrival at the trade deadline in 2019. The Raptors hoped the big Spanish centre could facilitate, defend, and be Philadelphia 76ers star Joel Embiid’s kryptonite when they acquired him. He delivered. In the post-season, Gasol helped hold Embiid to a measly 17.6 points and 37 per cent shooting in their seven-game series. The Raptors don’t get out of the second round and on the road to history without him. — Grange

#20. Danny Green

Criminally overlooked as merely a throw-in piece of the Kawhi Leonard trade, Green’s lone year in Toronto coincided with the most successful season in franchise history. He was a rock throughout Toronto’s championship campaign, shooting 45.5 per cent from distance in the regular season while leading the Raptors with 80 games played, all of them starts. And off the court he embraced an unfamiliar city — and country — with open arms, engaging with fans during live tapings of his popular podcast and hosting basketball clinics everywhere from Winnipeg to Halifax. — Zwelling

#19. Anthony Parker

At the age of 31, the man known as the “Michael Jordan of EuroLeague” brought his talents back to the NBA. After being a EuroLeague Champion and two-time MVP, Parker was a double-digit scorer and shot 42 per cent from three for the Raptors while more than holding his own on the defensive side of the ball. Parker helped usher in a winning mentality during his three seasons in Toronto and was a big part of the team’s first-ever Atlantic Division title in 2007. — Bennett

#18. Doug Christie

Christie was a top-end three-and-D role player before we even knew what that was. An instrumental part of the Vince Carter-Antonio Davis playoff years, Christie was counted on to both guard the opposing team’s best perimeter player and knock down the open shot (not necessarily a triple) when given the opportunity. Along the way, he also stuffed a few stat sheets. As a Raptor, Christie was always among the league leaders in steals and even recorded seven blocks in a game once. — Loung

#17. Serge Ibaka

Talented yet mercurial, Ibaka’s just as likely to leave you in awe when he takes over a game as he is to leave you flabbergasted when his worst instincts take over. You get the former more often than the latter, which is why Ibaka’s played 27 minutes or more a night each of his three seasons in Toronto, averaging 13.9 points, 7.1 boards, and 1.4 blocks per game. He made a new legion of fans last season with his utterly unique YouTube cooking show — in which he blends gross-out comedy with revealing celebrity interviews. Then those fans got to watch him selflessly grow into a crucial role player during the 2019 championship run, accepting fewer minutes and a position change for the betterment of the team. — Zwelling

#16. Amir Johnson

Johnson unfortunately was with the Raptors in some of the leanest years of the franchise, only getting a taste of the success to come in his final two seasons with Toronto. Still, he was a player who made the Raptors a team to cheer for even when they weren’t much fun to watch. He embraced Toronto and took part in a number of events in the city, including the Zombie Walk. And on the court, Johnson was an underrated player who could both catch a pass in traffic and finish when rolling hard. — Loung

#15. Charles Oakley

Arriving in Toronto in 1998 when the Raptors traded Marcus Camby to the New York Knicks, “Oak” brought a level of grit, work ethic, toughness and veteran savvy to the young franchise. His 18-foot jumpers and behind-the-back passes were the finesse plays that complemented his bone-crushing screens and hard fouls. His role as an enforcer allowed Vince Carter and Tracy McGrady to play freely and was greatly appreciated by fans. His greatest contribution may have been schooling the young, talented Raptors on what it meant to be a professional. He started in 207 of his 208 games as a Raptor, averaging 7.9 points per game and 8.0 rebounds. Some of the loudest ovations given to former Raptors upon their return have been reserved for Oakley. — Bennett

#14. Fred VanVleet

VanVleet’s “Bet on Yourself” backstory is an inspirational one of what hard work and perseverance can lead you to in life. He’s on this list because he’s always been a good player who can shoot the hell out of the ball — as evidenced by his Finals performance — but in signing with the Raptors he found the perfect marriage partner to let his talent shine. — Loung

#13. Alvin Williams

Before Kawhi Leonard hit “The Shot,” Williams was the owner of the biggest make in franchise history. With 42.9 seconds left in Game 5 of the 2001 first-round playoff series between the Raptors and New York Knicks, Williams hit a long two with the shot clock winding down to put the Raptors up six and, essentially, send the team to the second round for the first time in franchise history. Williams is remembered fondly for his steady play at point guard, but no moment stands out more than this one. — Loung

#12. Morris Peterson

It’s a testament to his skill and consistency that Peterson’s Toronto tenure began with the team’s first conference semi-final appearance in 2000-01, carried through the lean early aughts, and lasted all the way to the return to playoff contention in the heart of the Chris Bosh era. As players came and went, Peterson remained a productive, defensive-minded stalwart, providing steady three-point shooting, a gutsy eagerness to drive, and the occasional clutch circus shot. He left the franchise in 2007 as its leader in games played, a mark he held until DeMar DeRozan surpassed it in 2016. — Zwelling

#11. Tracy McGrady

T-Mac didn’t become a superstar until he left Toronto for Orlando and escaped the shadow of his cousin, Vince Carter, but during his formative years with the Raptors he offered several glimpses of the eventual two-time scoring champion he would become. And even though it’s likely you don’t remember much of McGrady’s Raptors career, we can guarantee you’ll remember at least one moment that he was a prominent part of, but gets next to no credit for. Without McGrady’s perfect bounce pass in the 2000 Slam Dunk Contest, Carter’s famous between-the-legs jam wouldn’t have happened. — Loung

#10. Pascal Siakam

Just how high Siakam’s ceiling resides is one of the most fascinating questions for Raptors fans and management alike as the franchise charts its future course. The 25-year-old Cameroonian was the NBA’s Most Improved Player last season, going from a raw, athletic, late-first-round project to a legitimate star and offensive focal point on a championship team. Blessed with the motor of all motors, Siakam’s creating and finishing skills are as unorthodox as they are effective, and his relentless, hounding defence can be a nightmare for guards and forwards alike. If he continues to develop at the rate he has — remember, Siakam began playing competitively less than a decade ago — we could be watching the emergence of an elite NBA talent. And whether or not he can fulfill that potential may be the most critical factor in how long the Raptors go between their first NBA Finals appearance and their next. — Zwelling

#9. Antonio Davis

The Raptors’ first all-star not named Vince Carter, Davis was a stabilizing force on the team’s first three playoff teams. He gave Toronto a hard-nosed defensive identity in support of Carter’s theatrics and just enough scoring. In his finest moment, Davis averaged 16.9 points and 10.4 rebounds in the Raptors’ seven-game series against the Philadelphia 76ers while going up against Hall of Fame defender Dikembe Mutombo. — Grange

“He was a skinny 19-year-old expected to heal a franchise’s post-Vince Carter heartbreak. He almost pulled it off, too.”

#8. Jonas Valanciunas

The most efficient low-post scorer the club has ever had, Valanciunas was drafted with the fifth overall pick in 2011 and was a polarizing figure from the start. Maligned for his defence and seen at times as out of step with the modern game, he learned to adapt — shuttling between starting and bench roles with grace and enthusiasm, and adding a three-point shot to his arsenal. After seven years with the club, his greatest Raptors moment may have been his gesture to come back and cheer on his old team after they had traded him. It’s a shame he wasn’t on the team when they finally got over the hump, because I’m not sure any Raptor sacrificed more. That won’t go without acknowledgement — if Kyle Lowry has anything to say about it, the team is expected to present him with a ring before much longer. — Bennett

#7. Jose Calderon

Though his defence frustrated many a Raptors observer, Calderon is an all-time Raptor not only because he had a 50-40-90 season (despite the fact Wikipedia claims he didn’t) but because he was a constant during a tumultuous period of Raptors history. Joining the club at the very end of the Rob Babcock era and leaving just before the fortunes of the franchise were about to turn, Calderon was an endearing fan favourite when one was needed most. — Loung

#6. Damon Stoudamire

Before there was Vince Carter, there was “Mighty Mouse” Damon Stoudamire, the Original Raptor. Taken with the seventh-overall pick in the 1995 draft, Stoudamire would go on to win Rookie of the Year in the franchise’s inaugural season. Though his Raptors tenure was shorter than most would’ve liked (he was traded in Feb., 1998), Stoudamire is still a key figure in Raptors history as he helped give the franchise some desperately needed star power in its earliest days. — Loung

#5. Chris Bosh

He was a skinny 19-year-old expected to do the impossible: Heal a franchise’s post-Vince Carter heartbreak. He almost pulled it off, too. Taken fourth overall in the legendary 2003 draft, Bosh came to a team that had nowhere to go but up, although with no clear path to get there. He quickly made his mark. He was an all-star in his third season (the first of 11 straight nods), kicking off a five-year stretch during which he averaged 22.8 points and 9.9 rebounds a game on 50 per cent shooting — the only player in the NBA to reach those marks over that time frame. He led the Raptors to three consecutive playoff appearances and the brink of a fourth, but Bosh could never get Toronto out of the first round. As much as his game had evolved, Bosh needed help to go deeper in the post-season, and after seven seasons he went to Miami to find it. — Grange

#4. Vince Carter

Where to begin with Vincent Lamar Carter? There’s no denying that the way things ended between him and the Raptors was, to put it lightly, unideal, but his contributions to the Raptors and basketball in Canada in general can’t be denied. Yes, his greatest accomplishment is probably only a dunk contest win, but without Carter there might not even be a Raptors anymore, let alone an NBA championship. It’s OK to be upset with the man once known as “Air Canada,” but he was the catalyst for everything that followed, and as such, is deserving of being considered one of the best in franchise history. — Loung

#3. DeMar DeRozan

“Don’t worry, I got us.” Five words that encapsulate DeRozan perfectly. He is Mr. Raptor. For all his flaws as a player, DeRozan will always be loved because no other player of significance embraced the franchise the way he did. Drafted ninth overall in 2009, DeRozan grew up right before Raptors fans’ eyes, earning four all-star nods and being named to two all-NBA teams. He’s the franchise leader in games, minutes, points and a host of other leaderboards. And as much as fans grew to love him, he reciprocated that love. He never wanted to leave and, in some ways, he never did. DeRozan will forever be a Raptor in Toronto fans’ hearts. — Loung

#2. Kawhi Leonard

Leonard’s stint in Canada may have been brief, but his legacy will always be the Most Valuable Player on the first championship team the franchise has ever seen. The bouncing buzzer beater versus Philly, the dunk on Giannis, the domination of the Warriors — Leonard’s resumé was fortified in a dominant playoff run. Not only did he become the third Finals MVP to have won the award with two teams, he is also the first person to win Finals MVP with a team from each conference. Facing double and at times triple teams and often performing on one leg, Leonard scored 732 points during the 2019 playoffs, the third-highest scoring total for a single NBA post-season. He wasn’t here nearly as long and wasn’t nearly as charismatic, but in a couple of generations the “Kawhi effect” will likely be even stronger than the “Carter effect.” — Bennett

#1. Kyle Lowry

Kyle Lowry taught Canada how to appreciate basketball. That’s just one of his accomplishments over the course of his rise to the peak of a quarter-century of Raptors players. There are plenty more: The five all-star games, the franchise records for three-pointers made, steals, triple-doubles and — barring anything unforeseen in the 2019–20 season — eventually assists. He’s won more playoff games than any Raptors player and he’s the franchise leader in championship rings consulted on.

But Lowry’s legacy is more significant and more subtle than the bling or the records or even all the winning. Lowry provided those who watched closely a complete basketball education. The franchise has never had a player as savvy, clever or competitive. We’ve become a smarter basketball nation as a result. His feel for time and situation; his uncanny knack and unfailing nerve for stepping in and drawing charges; and the fierceness with which he approached every moment and battled for every call. The smile he would flash when the goal was reached.

Other Raptors may have wowed us more; some were more gifted scorers. Plenty might have looked smoother doing their thing. None got more done on the floor than Kyle Lowry. — Grange

Edited and designed by Craig Battle and Gary Melo.

Photo Credits

Frank Gunn/CP (Ford; Green/Gasol; Lowry/Leonard); Aaron Harris/CP (Oakley); Fernando Medina/NBAE via Getty Images (McGrady); Ron Turenne/NBAE via Getty Images (Bosh/Carter)