Counting Down the Five Greatest Raptors Point Guards of All Time

By Pete Baxter

Through the Raptors 2.5 decades of existence, they have had some exciting highs, none greater than their 2018 NBA Championship victory. The Raptors and their fans have also battled through some of the deepest lows you can imagine, as a struggling, fledgling franchise through the late 90s and mired with such disfunction in the early 2000s that they ran their greatest star ever (up to that point, anyway) out of town.

Naturally, the franchise’s success (or lack thereof) hinged on the talent they could put on the floor. No position in basketball is more influential than the point guard, and thus the state of the squad was often a reflection of the team’s floor general during a given season.

With that said, let’s take a trip down memory lane and explore the relatively short (but eventful) history of the Toronto Raptors, and dig deeper into the characters that have held the reins to the offense since they exploded onto the scene with their vibrant purple jerseys in 1995. We will attempt to fairly weigh statistical achievement, impact on the franchise, and tenure as we nail down a list of the top five Raptor greats at the position.

Let’s jump right in:

Honorable Mentions

There are just too many fascinating characters in the history of the Toronto Raptors to not at least shout of the guys who couldn’t quite make the cut. Gone but not forgotten, let’s take a quick look at some honorable mentions:

Rafer Alston, aka streetball legend “Skip to My Lou” had two different one-year stints in Toronto (2002/03 and 2004/05). The second of his seasons as a Raptor was the best of his NBA career, as he averaged 14.2 points, 6.4 assists and 1.5 steals per game. Unfortunately, this was during a dark time in franchise history as the Raptors gradually moved on from an injured and disgruntled Vince Carter. The team never won more than 33 games during Alston’s tenure. However, he will always be remembered for bringing the exciting playmaking and flare of the AND1 Mixtape Tour into the NBA. He could put on a hell of a show.

Mark Jackson played just 54 games in Toronto while on the back nine of his career. However, his statistics during that lone partial season hold up, and remain one of the best performances in terms of assists in the team’s history. He averaged 8.5 points and 9.2 assists during the 2000/01 campaign before being traded at the deadline to the Knicks.

Chauncey Billups was a Toronto Raptor long before he became a champion and legend with the Detroit Pistons. His future success is the only reason he appears on this list, as he in fact only played 26 games as a Raptor during his rookie 1997/98 campaign, in which he averaged a respectable 11.3 points per game. It is fun to imagine if he had stuck around and joined Vince Carter and Tracy McGrady just a couple years later, though…

Mike James put up one of the most unlikely 20+ point per game seasons ever on a bad Raptors squad in 2005/2006. James was a borderline All Star over that 79-game stretch, in which he played 37.0 minutes per night while averaging an impressive 20.3 points and 5.8 assists while shooting over 44% from three-point range. In fact, late in the season, James became the first player in franchise history to score 30+ points in four consecutive games. Unfortunately, the Raptors won just 27 games that season, and James signed with Minnesota the following season, where his career began a swift decline.

T.J. Ford had two solid seasons as the Raptors’ starting point guard in the midst of the Chris Bosh era.The best season of Fords career came during the 2006/07 season, in which he put up 14.0 points, 7.9 assists, and 1.3 steals per game. He helped lead the team back to the playoffs, tying a franchise-best 47 wins. Unfortunately, he returned to his injury-and-turnover-prone ways the following season, and ultimately lost his starting position to Jose Calderon. Ford was traded to Indiana after the 2007/08 season.

Oh, and shoutout to Muggsy Bogues. He only averaged 5.1 points and 3.7 assists in the final games of his career in Toronto, but the 5’3” legend did help mentor a young squad led by VC and TMac that would go on to make the playoffs.

And with that, let’s move on to the Top Five Raptors Point Guards of All Time!

#5. Alvin Williams

Williams was never a star in the league, but he was a fan favorite, a stabilizing presence, and reliable backcourt running mate for Vince Carter in the late 1990s and early 2000s. Williams was the primary floor general during the peak Carter years, and spent 6+ seasons in Toronto. His best season statistically came in 2002/03, in which he averaged a respectable 13.2 points, 5.3 assists and 1.3 steals per game. He helped the Raptors reach the playoffs in three straight seasons from 1999/00 through 2001/2002, including the team’s first trip to the Eastern Conference Semis in 2000/01.

Unfortunately, Williams’ career would be slowed and eventually cut short by nagging knee injuries. He would return to the Raptors as an assist coach in 2009. Williams joins the likes of Amir Johnson and Jerome Williams as reliable, tough, leaders in the history of the Raptors, despite their statistics not jumping off the page.

#4. Jose Calderon

Jose Calderon took the reins after the team opted to move on from T.J. Ford (after sharing point guard duties with him during his rookie and sophomore seasons). Calderon spent the first seven+ seasons of his career as a Raptor (from 2005/06 to 2012.13) after being signed as an undrafted free agent out of Spain. He became known for his elite shooting and passing despite his relative lack of athleticism (that eventually made him a defensive liability). Calderon led the league in free throw shooting at an incredible 98.1% in 2008/09 and led the league in three-point percentage in 2012/13 at 46.1%. His best statistical season came during that 2008/09 campaign in which he averaged 12.8 points, 8.9 assists, and 1.1 steals per game. Calderon also led the Eastern Conference in assists for that season with a borderline All-Star effort.

Unfortunately, Calderon’s career in Toronto essentially took place during the second dark age of Raptors basketball between the Carter era and the Lowry/DeRozan era, and the team only made the playoffs twice during his tenure, losing in the first round both times. Calderon was eventually traded to the Detroit Pistons in the trade that brought Rudy Gay (briefly) to Toronto. He is still the franchise’s all-time leader in free throw percentage at 87.7% during his Raptors career.

#3. Damon Stoudamire

Stoudamire, AKA Mighty Mouse, was the first ever draft pick by the Raptors in 1995 and became their first star. He hit the ground running in Toronto with an outstanding rookie campaign that saw him win Rookie of the Year while earning All-Rookie-First Team honors. He is still the shortest player to ever win Rookie of the Year at just 5’10.” Stoudamire averaged an impressive 19.0 points, 9.3 assists and 1.4 steals per game while setting a then rookie record with 133 made three-point shots.

Stoudamire only got better in year two, bumping his scoring up to 20.2 points per game with 8.8 assists and 1.5 steals, helping the brand-new franchise improve from 21 to 30 wins (a modest improvement) while getting snubbed from the All-Star game. Stoudamire only spent 2.5 seasons as a Raptor before being traded to the Portland Trail Blazers during his third season for a handful of role players and plethora of draft picks.

To this day, Stoudamire still holds the franchise record for assists per game with 8.8 during his Toronto tenure, as well as minutes per game at 41.0 (dude put in that work). Stoudamire will always be a legend in Toronto as their first star player, despite his brief tenure.

#2. Fred VanVleet

The past decade has been very good to Toronto basketball. The franchise won their first NBA title in 2018/19 and has managed to have a smooth transition between the two greatest point guards in their franchise’s history.

Fred VanVleet’s legacy is already an impressive one, as arguably the greatest undrafted NBA player in modern times. He joined the Raptors as an undrafted free agent out of Wichita State for the 2016/17 season, and by his second year he had become a key member of the team’s “bench mob.” By his third season, VanVleet played an invaluable role as back up point guard, sometimes starting shooting guard, and clutch three-point bomber as Kawhi Leonard and company brought the first NBA title to Toronto.

The following season, after the departure of key veterans Kawhi Leonard, Serge Ibaka, Marc Gasol, and Danny Green, VanVleet finally became a full-time starter and his numbers jumped to borderline All-Star levels. As the team’s starting shooting guard next to Kyle Lowry, VanVleet averaged 17.6 points, 6.6 assists and 1.9 steals per game as the Raptors returned to the playoffs and fell just a game short of the Eastern Conference Finals in the Orlando bubble.

This season, following the departure of Kyle Lowry to Miami, VanVleet has finally become the team’s true starting point guard, and his numbers have taken another notable jump. Through 41 games in the 2021/22 season, VanVleet has proven himself the clear-cut leader of the team, while putting up rock solid averages of 21.7 points, 7.0 assists, 4.7 rebounds, and 1.7 steals while shooting just under 40% from three-point range. He very well may make his first All-Star appearance.

If this current Raptors core of VanVleet, Pascal Siakam, O.G. Anunoby and company can reach their full potential and bring another championship to Toronto, VanVleet could very well challenge for the top spot on this list in the future. Either way, he is already a Raptor legend at just 27 years old.

#1. Kyle Lowry

Finally, that brings us to the top spot on the list. Kyle Lowry is considered by many to be the greatest Toronto Raptor of all time, and he is the unquestioned greatest floor general in franchise history. While Kawhi Leonard is deservedly remembered as the best player on that 2018/19 championship squad, Kyle Lowry was without question the motor and leader of that unit.

Lowry made six consecutive All-Star appearances as a Raptor while leading the team (along with best friend and backcourt mate DeMar DeRozan and later the young core of Siakam/VanVleet/Anunoby) to seven straight playoff appearances. Even before Kawhi arrived in Toronto in that trade for DeRozan, Lowry had already led the Raptors the Eastern Conference finals where they had pushed Lebron’s Cavaliers to six games.

Kyle Lowry is the franchise’s all-time leader in assists, steals, triple doubles, three-point field goals, three-point attempts, turnovers, and fouls, as well as metrics like win shares and value over replacement.

Lowry is a champion, an All-Star, and the Raptor’s GOAT. With his return to Toronto coming up as the Heat come to town on February 1st, let’s hope he gets the warm Jurassic Park welcome he deserves! All hail the Point God GOAT!

Looking Forward

Stay tuned as we count down the franchise’s top shooting guards, small forwards, power forwards and centers over the coming weeks, and eventually rank the greatest overall Raptors in franchise history.  More to come from Toronto!

Published by Pete of the North

Avid sports fan and obsessed statistician. Binge drinker turned writer. Toronto Raptors fan since the O.G. Zan Tabak. Based out of Albany, NY. Cheers!

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