Counting Down the Raptors’ Top Ten Shooting Guards of All Time

By Pete Baxter

Having previously counted down the top five point guards in Toronto Raptors’ franchise history, it is time to jump right in and take a look at the greatest shooting guards to ever grace Raptors’ purple (or black or gold or red or white).

To be honest, this list began as a top five. However, by the time I narrowed it down to ten players, I just couldn’t bring myself to exclude anyone else. So, for the first time, we will officially bump the list up to a top 10.

In basketball, there tends to be fluidity between positions. Therefore, some guys who appear on this list may have done double duty as point guards or small forwards (or even power forwards) at times. Conversely, there are players who won’t appear on this list because, while they spent time playing two guard in the Six, their primary position lies elsewhere. For example, we ranked Fred VanVleet as a point guard, and Tracy McGrady, Mo Peterson, and Jalen Rose will be considered small forwards in this series (spoiler alert, stay tuned for the top-ten small forwards next week).

With all that said, this is a hell of a list. Two of the top-four Raptors of all time appear on this list. The Raptors’ first ever super star appears on this list. A key part of the Raptors’ lone NBA Championship appears on this list. Without further ado, let’s jump right in!

#10. Dell Curry

The father of Steph and Seth Curry ended his playing career in Toronto as a sharpshooter off the bench and a mentor to a young Vince Carter. He helped the team to their first playoff appearance. While he never averaged more than 7.6 points per game during his three-year run as a Raptor, Curry shot nearly 43% from three-point range in 2000/01.

#9. Dee Brown

Brown is one who could have been listed as a one or a two on a given night, but for the purposes of these rankings, we will list him as a shooting guard since he already missed the cut as a point guard. Brown spent two-and-a-half seasons at the tail end of his career in Toronto. During his best full season as a Raptor in 1998/99, Brown averaged 11.2 points, 2.1 boards, 2.9 assists and 1.1 steals as essentially the team’s sixth man. Brown also played a key role as a sometimes-starter in the Raptors’ first playoff appearance in 1999/00. Unfortunately, Brown may be most known for missing the potential game winning shot in closing seconds of a playoff loss to the Knicks.

#8. Anthony Parker played a key role as the starting guard (and sometimes forward) on two Raptors’ playoff squads in 2006/07 and 2007/08. After spending six seasons playing in Europe and Israel (following three anonymous seasons as a benchwarmer in Philadelphia and Orlando), Parker returned to the NBA in 2006 with a bang. He had become an elite shooter, hitting over 44% of his three-point shots in 2006/07. His three years in Toronto were the best of his career, peaking in 2007/08 in which he averaged 12.5 points, 4.1 rebounds, 2.2 assists, 1.0 steal and hitting 1.6 three-pointers per game with 43.8% accuracy.

#7. Lou Williams only spent one season as a Raptor, but it was a hell of a season. Williams won Sixth Man of the Year during that 2014/15 season while averaging 15.5 points per game in just 25.2 minutes with zero starts. Williams is one of the greatest offensive sparkplugs to ever come off an NBA bench, and he was a key member of a Raptors team that won 49 games.

#6. Gary Trent Jr.

It is a testament to how good Gary Trent Jr. is that he is already this high up the list despite playing in just 54 total games for the Raptors. Since being acquired from the Portland Trail Blazers in trade for Norman Powell, Trent Jr. (who’s father briefly played for the Raptors in the franchise’s early days) has been electric. He has averaged over 16 points per game as a Raptor while hitting 2.7 three-pointers per game at 36.5% accuracy. He dropped a career-high 44 points against the Cleveland Cavaliers in April of 2020. There is no doubt that, if he sticks around Toronto as part of their talented young corps, he will be considerably higher up this list very soon.

#5. Norman Powell

Interestingly, just ahead of Trent Jr. on the list is the man who was traded away to acquire him. Norman Powell has built himself a hell of a career for a mid-second-round draft pick (drafted at 46 by the Bucks in 2015, though he was immediately traded to the Raptors along with picks for Greivis Vasquez). By the end of his rookie season, Powell had become a key part of the Raptor’s rotation, splitting time as a stand-in starter and key member of the team’s bench mob.

After four years of gradual improvement in primarily a reserve role, and winning a championship off the bench in 2018/19, Powell’s role increased dramatically in 2019/20 after Kawhi Leonard and Danny Green left town. Powell averaged 16.0 points per game while shooting nearly 40% from three on the season. His physical strength allowed he match up effectively on both ends of the court against bigger players, even spending significant time at the three-spot despite being just 6’3.” He had a strong season for a young Raptors squad that came just a game short of making the Eastern Conference finals in the NBA Covid Bubble.

He took another step forward in 2020/21, starting 31 games through the first half of the season for the Raptors while averaging 18.6 points per game and shooting over 41% from three. Unfortunately, the Raptors took a step back as a team while playing their home games in Tampa, Florida. The Raptors wanted to make moves at the trade deadline, and Powell was traded to the Portland Trail Blazers for Gary Trent Jr. after 5.5 seasons as a Raptors. He is a still a fan favorite in the Jurassic Park.

4. Doug Christie

While Christie is best known for his time with Chris Webber and company on a contending Sacramento Kings squad, he got his first taste of success as one of the best players on a young Raptor’s squad. Christie spent 4.5 seasons as a Raptor after being acquired half-way through the team’s inaugural season. Christie quickly became one of the team’s best players as an outstanding wing defender and effective scorer.

The best season statistical season of his career came in Toronto during the 1997/98 season, in which he averaged 16.5 points, 5.2 boards, 3.6 points and 2.4 steals per game while starting 78 games. He helped the Raptors make their first playoff appearance in the 1999/2000 season alongside rising star Vince Carter and company, before he was traded to the Sacramento Kings for Corliss Williamson.

3. Danny Green

Danny Green spent just one season in Toronto, but the leadership, tenacious defense, shooting, and winning pedigree that he brought to the squad played a key role in the team’s 2018/19 NBA Championship win.

Green had already won an NBA championship as the starting shooting guard for the San Antonio Spurs before coming to Toronto (along with Kawhi Leonard) in the trade that sent DeMar DeRozan out of town. While it was a highly emotional decision to let DeRozan go, the trade led to the ultimate short-term success.

While Green’s statistics didn’t jump off the page as a Raptor (he averaged 10.3 points, 4.0 rebounds, and 1.6 assists on the season), his elite defense and shooting (45.5% from three) had a massive impact on the team. In another example of the many heartbreaking personnel losses in the team’s history, both Green and Kawhi Leonard turned out to be one-year rentals, and Green himself moved on to join the Lakers in 2019/20 where he would win his third NBA Championship.

2. DeMar DeRozan

Naturally, that brings us to the Raptors’ legend who was sent away in the trade that brought the aforementioned Green to Toronto. This will be the most controversial placement decision on this list, as there is a major argument to be made that DeRozan should be number one.

DeRozan spent nine seasons in Toronto as a loyal, homegrown talent. He became a four-time All-Star as a Raptor, and along with his backcourt mate Kyle Lowry led the Raptors to five-straight playoff appearances, including the franchise’s first trip to the Eastern Conference Finals in the 2015/16 season. Unfortunately, the team once again was eliminated by Lebron James and company. After the team failed to make it past the second-round of the playoffs during the following two seasons, Masai Ujiri and company made arguably the biggest trade in franchise history, sending DeRozan to San Antonio for that package headlined by Kawhi Leonard.

DeRozan, perhaps the most loyal star the Raptors had ever had, was heartbroken after the trade and still talks about it to this day. Fans were split at the time. Many were livid that the team had moved on from one of its top-three greatest players and were afraid Leonard would simply refuse to report to Toronto. Fortunately, in the short-term, the trade worked out pretty damn well for Toronto as we have discussed. That said, DeRozan is one of the greatest players in Raptors’ history, and helped the team achieve it’s longest stretch of winning basketball in the history of the franchise. He will always be a Raptors legend.

#1. Vince Carter

And that brings us to the high-flying NBA legend who put Toronto basketball on the map at the turn of the millennium. While Vince Carter didn’t have the tenure or quite the playoff success that DeRozan did during his time in Toronto, the impact that he had on the young franchise, on basketball in Canada, and on the game itself puts him over the top as the greatest shooting guard in team history.

And yes, Carter did spend a lot of time at the small forward spot as well. However, because I am biased and my favorite lineup of his era featured Carter at the two and McGrady at the three, we are considering Carter a shooting guard for the purposes of these rankings.

Carter had an often-amazing, sometimes controversial 6.5-year run in Toronto. He won Rookie of the Year honors in 1998/99 after being acquired by Toronto on draft night from the Golden State Warriors for the rights to his college teammate Antawn Jamison. This turned out to be an outstanding deal for the Raptors, as Carter went on to be a six-time All-Star for Toronto (including the year he was traded) while becoming arguably the most popular player in the world for a time. He led the Raptors to their first-ever playoff appearance during his sophomore season in which he averaged 25.7 points per game with 5.8 rebounds, 3.9 assists, 1.3 steals and 1.1 blocks and shot over 40% from three-point range.

During the 2000 NBA All-Star Weekend, Carter essentially re-invented the Slam Dunk Contest in an incredible victory that is considered by many to be the greatest performance in the history of the competition.

His third season was even better, as he went on to average a franchise record 27.6 points, 5.5 rebounds, 3.9 assists, 1.5 steals and 1.1 blocks per game. The Raptors would finish just a last second shot by Carter away from the Eastern Conference Finals in a loss to Allen Iverson’s 76ers squad (Carter drew controversy for choosing to fly to North Carolina for his college graduation earlier in the day).

Unfortunately, “Air Canada” and the franchise that made him a global star had an ugly, slow-motion falling out over the next few seasons. Carter struggled to stay on the court, and gradually became disengaged from the team. He butted heads with the front office and their coaching selections. Eventually, things became so tense that the Raptors were forced to trade their disgruntled star, and Carter was sent to the New Jersey Nets for a weak package headlined by Alonzo Mourning (who refused to report to Toronto) and two first-round picks.

It was a disappointing ending to what had been an incredible run in Toronto. After more than a decade of raining boos during his return trips to the city and country that made him an NBA legend, late in his career Carter finally received a standing ovation from Raptors fans during a video tribute. Carter and the Raptors’ fan base finally made peace.

Looking Ahead

As noted, Gary Trent Jr., at just 23 years old, will very likely move up towards the three-spot over the next season or two. He helps round out a very exciting young core along with Fred VanVleet, Pascal Siakam, Scottie Barnes, and O.G. Anunoby. Dalano Banton, an oversized guard who can seemingly play anything from the one through the four, could also develop into a solid rotation player in the backcourt and could find himself on this list soon as well.

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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