Founded in 1995, the Toronto Raptors have hosted several modern NBA greats and fan favourites, but in 2019, the Canadian team finally broke through to become NBA champions for the very first time. 

Naturally – even with many of their top performers still being active – a bunch of the 2019 Raptors and those who played important roles in getting the team playoff-ready rank among the franchise’s greatest players.

Keep scrolling to find out who ranks among the very best players ever to pull on a Toronto Raptors jersey.

1. Kyle Lowry

Very, very few, if any, NBA fans would dispute Kyle Lowry as the greatest player to ever play for the Raptors, being pivotal during the championship run and throughout his nine-year stay in Canada.

After bouncing from the Memphis Grizzlies to the Houston Rockets between 2006 and 2012, when he finally landed in Toronto, Kyle Lowry certainly wasn’t expected to explode into an NBA All-Star.

Still, as a Raptor, Lowry collected all six of his All-Star call-ups and remains the franchise leader for three-point field goals, assists, win share, and steals. 

2020/21 would end Lowry’s much-lauded time in Toronto, but now with the Miami Heat, he’s certainly in the mix to win another NBA Championship at +800 in the NBA odds.

2. DeMar DeRozan

DeMar DeRozan was Toronto basketball for the better part of a decade. Picked 9th overall in 2009, by 2014, he was an All-Star, stacking up gaudy stat lines and making Toronto relevant again.

Beloved by the fans, he’s still topping the franchise’s charts for games, minutes, field goals, and free throws. However, he was, unfortunately, who the front office gambled away for a shot at the title. 

It proved to be the right play, but seeing DeRozan get traded with little regard to the player who had entrenched himself in Toronto was a rough way to start the season. 

Now, he’s on the books of the Chicago Bulls, helping to bring through the young guns. Just as we saw in Toronto, his presence in the locker room adds heaps of value, even to the extent that some call the 33-year-old almost untouchable in the trade market.

3. Kawhi Leonard

Quite possibly the most impactful single-season player for any team in NBA history, Kawhi Leonard’s stay in Toronto was certainly brief, but it was exactly what a team with championship aspirations needed.

The Raptors bet the farm, and then some, on Leonard being the final piece of the puzzle, even sending away DeRozan and a first-rounder for who was widely considered to be the best defensive player in the league.

With only one year left on his contract, the job was simple: win Toronto the title. “Klaw” did exactly that, playing 24 games in the postseason with averages of 39.1 minutes, 49.0 field goal percentage, 2.3 offensive rebounds, 6.8 defensive rebounds, 3.9 assists, and 30.5 points. 

Leonard delivered, and then some, for Toronto. Now back home with the Los Angeles Clippers, he has an outside shot of being on another title-winning team at +1200 in the basketball betting

4. Vince Carter

One of the most exciting players of 00s NBA, Vince Carter was technically picked fifth overall in 1998 by the Golden State Warriors, but would become a legend in Toronto after an immediate switch for the fourth pick of the draft.

He powered the young franchise to its first-ever postseason, but everyone remembers Carter for his awe-inspiring aerial ability. Dunks and absurd acrobatics were the hallmarks of his play from his NBA Rookie of the Year season onwards. 

With six years as a Raptor under his belt, Carter and several other stars moved on as part of a massive 2004 reshuffle.

He was often booed when he returned to Toronto in another jersey, but ‘Air Canada’ is more often considered much more fondly now that his incredible 21-year NBA playing career has come to an end.

5. Chris Bosh

Chris Bosh was the face of the franchise to replace Vince Carter, having been invested in heavily with a fourth overall pick in the 2003 draft. 

Up to the end of the 2009/10 campaign, Bosh was superb for Toronto, securing five of his eventual 11 All-Star call-ups and setting new bars in just about every statistical category. 

In the summer of 2010, Bosh would be part of a multi-player movement that would change the NBA forever.

Working a move to the Miami Heat, he joined LeBron James and Dwyane Wade to forge what was essentially the first “superteam” to be put together by players directly. 

Bosh would finish his career with Miami, adding back-to-back NBA Championships in 2012 and 2013 to his glittering career. 

6. Damon Stoudamire

The first true draft pick for the Toronto Raptors, Damon Stoudamire arrived as an exciting point guard worthy of the 7th overall pick.

In his first season (1995/96), he proved that by landing the Rookie of the Year Award.

Through three seasons, Stoudamire put up points averages of 19.0, 20.2, and 19.4 as a key piece of the team, but demanded a trade amidst the 1997/98 season and joined the Portland Trail Blazers. 

Raptors fans can take solace in the knowledge that Toronto saw the very best of Stoudamire, when he played the most minutes and was putting up the most points. 

7. Pascal Siakam

Born in Cameroon, Pascal Siakam isn’t only a significant figure in Toronto Raptors history, but also in NBA history.

In 2020, the power forward became the first G League graduate also to be an All-Star starter.

For the Raptors, the time put in from 2016 to 2018 paid dividends in the 2018/19 campaign, with Siakam blossoming into a starter, averaging 16.9 points, and playing a key role in their run to the title.

Most impressively, the Championship-winning season was just the beginning for Siakam individually, as his averages have only improved since, and he landed his second All-Star nod just last season.

8. José Calderón

One of the most selfless point guards to step foot on Toronto’s court, José Calderón came to the Raptors undrafted and 24-years-old, but he’d become a key part of what made others like Chris Bosh so strong statistically.

The Spaniard once held the franchise record for assists put up during his seven-and-a-half run as a Raptor, and while Lowry has since eclipsed him, Calderón can still boast a top-ranking .877 free throw percentage.

9. Jonas Valančiūnas

Further proving the historic prowess of the Toronto Raptors when the franchise picks early, Jonas Valančiūnas arrived from Lithuania via the fifth overall pick in the 2011 Draft.

By the 2012/13 season, he was a regular starter.

The towering and incredibly adaptable center did everything that was asked of him, but in a cruel twist, Valančiūnas was traded to the Memphis Grizzlies at the deadline of what would prove to be Toronto’s championship season. 

10. Fred VanVleet

At the time of writing, Fred VanVleet only signed for the Houston Rockets on a hefty $130 million, three-year deal two days ago. Still, that didn’t influence his ranking among Toronto’s greatest-ever players.

Like Siakam, VanVleet was undrafted, picked up by the Raptors, and assigned to the G League to enhance his skill. The 6’0’’ guard did exactly that and was rewarded with regular starts in the 2018/19 season.

He broke through just in time to win the NBA Championship, and through the more turbulent seasons thereafter, VanVleet transformed into one of the team’s star players and a 2022 All-Star.

*Credit for all images in this article belongs to AP Photo*

Ben is very much a sports nerd, being obsessed with statistical deep dives and the numbers behind the results and performances.

Top of the agenda are hockey, soccer, and boxing, but there's always time for the NFL, cricket, Formula One, and a bit of mixed martial arts.