Ranking the five greatest Raptors of all-time

Let’s start off by making sure we know the difference between greatest and best. There’s not a doubt in my mind that Kawhi Leonard is the best player to ever play for the Raptors, but that’s not how we define greatness. When you’re thinking about the greatest players to ever play you have to factor in things like longevity, leadership, winning, and the ‘it’ factor, along with their talent and ability. I think there’s overall agreement of who deserves to be in the top five, especially the top four, but a lot can be debated about the order, so be prepared to disagree with me. At the end of the day the final ranking is based on my personal opinion. Now, let’s take a deep dive into the five greatest Raptors of all-time.

5. Chris Bosh, PF/C, 2003-2010

Bosh played for the Raptors for seven seasons after they drafted him fourth overall in the 2003 draft. He played his rookie year alongside Vince Carter (who appears a little later on this list), before Vince Carter was moved to the New Jersey Nets in the middle of Bosh’s second NBA season. After losing their most impactful player in Carter, the franchise for the rest of Bosh’s tenure was built around him, and he stepped up into the leading role. After averaging 16.8 points per game in his second season, Bosh wouldn’t go another season with the Raptors averaging fewer than 20 points and 8.7 rebounds per game. A five-time all-star in Toronto, the Raptors only made two playoff appearances while Chris was on the team, and lost in the first round both times. Bosh kept the franchise afloat during the years between Vince Carter and DeMar Derozan, and much of the Raptors’ culture was built during the years of Chris Bosh. For that, and for his consistent all-star caliber play, he’s earned a spot on this list.

4. Vince Carter, SF/SG, 1998-2004

Some might argue that Vince appears too low on this list, and that’s understandable. Vince “Air Canada” Carter put Toronto on the map in the NBA. Arguably the second BEST player ever to play for the Raptors, the Golden State Warriors drafted him fifth overall in the 1998 NBA draft. He was then traded to Toronto for the fourth overall pick, Antawn Jamison. In his first year with the Raptors, he quickly became a fan favourite in Toronto, mostly due to his high-flying, poster-dunking nature. In just his second season, Vince Carter was named to the third team all-NBA while averaging 25.7 points per game. Earning the nicknames “Vinsanity”, “half-man, half-amazing” and the aforementioned “Air Canada”, Vince appeared in the dunk contest in his second year. Known for being possibly the greatest dunk contest of all-time, Carter put on a show (seriously though, go watch the highlights), putting him in the spotlight of the entire league. In just his third season, Vince averaged over 27 points per game and was named to the second team all-NBA, leading the Raptors into the playoffs where they would meet MVP Allen Iverson and the 76ers in the conference semi-finals. Carter and Iverson went back and forth all series, pushing the series to a deciding seventh game. In an infamous decision, Carter decided to attend his university graduation the morning of game seven, before flying back in for the game. After a hard-fought battle, Carter missed a shot at the buzzer that would have sent the Raptors to the conference finals with a good chance at their first ever NBA finals appearance. Unfortunately that’s as deep as the Raptors would get in the playoffs with Carter at the helm, and after a few more all-star seasons and some problems between Carter and Raptors management, he was traded to the Nets. Although things didn’t end well with Vince Carter in Toronto, he was the first player to bring real significance to Canada’s only NBA team, and is tough to have this low on the list.

3. DeMar DeRozan, SG/SF, 2009-2018

DeMar DeRozan was the first star player to ever truly love Toronto, and Toronto loved DeMar DeRozan. After being drafted by the Raptors in 2009, DeMar became the heartbeat of Toronto basketball. Few players (in fact only one other player) was beloved by Toronto fans as dearly as DeRozan was. When Chris Bosh left to play with LeBron James and the Heat in the 2010 offseason, DeRozan famously tweeted “Don’t worry, I got us…”. That tweet gives me goosebumps to this day. Carter wanted out of Toronto and got sent away to the Nets, Bosh left to play for the Heat, but DeRozan told Toronto fans he was here to stay, and he was true to his word. A four time all-star with the Raptors, DeMar stepped up his production after Bosh left, making a jump from 8.6 to 17.2 points per game in his second season. DeRozan never averaged less than 20 points per game after his first all star season in 2013-14, and consistently played his heart out for Toronto. DeMar is the Raptors all-time leader in games played, minutes played, and points scored (at least for now, Kyle Lowry could have a say in that soon). DeRozan played his heart out for the Raptors each and every year, but they couldn’t get over the hump in the playoffs. After being eliminated by the LeBron James led Cavaliers for the third consecutive year, team president Masai Ujiri decided it was time for a change. He moved away from DeRozan, onto the next player on this list, and it proved to be the right decision. It pains me to have DeRozan so low on the list, but the two players above him both have the one thing DeMar could never quite get.

2. Kawhi Leonard, SF, 2018-2019

A championship. That’s the one and only reason I rank Kawhi Leonard above DeMar DeRozan as the second greatest Raptor ever. Many of you will disagree with me here, and I understand why, but Kawhi took us home. After over 20 years of existence without a finals appearance, much less a championship, Masai Ujiri traded DeMar Derozan, Jakob Poeltl, and a first-round pick in return for disgruntled superstar Kawhi Leonard and Danny Green. There were doubts about Kawhi’s willingness to play in Toronto, as well as his ability to stay healthy after playing only nine games the previous season. Both of those doubts proved to be unfounded. Kawhi showed up in Toronto and went to work, and the Raptors staff handled his recovery from injury perfectly, playing him in only 60 games to keep him fresh for the playoffs. And fresh he was. After an all-star season averaging 26.6 points and 7.3 rebounds per game, Kawhi elevated his game to a whole other level in the playoffs. Leonard averaged 30.5 points and 9.1 rebounds in the 2019 playoffs, including some heroic performances – such as the 52 minute, 36 point double overtime game three against the Bucks in the conference finals, or the 39 point, 14 rebound game four against the 76ers in the semi-finals – that kept the Raptors afloat in the playoffs. And we will never forget the greatest shot in Raptors history, the game seven buzzer beater over Joel Embiid to send the Raptors to the conference finals. Kawhi was the driving force behind the first Raptors team to ever make a finals appearance, and led them to a six-game victory over the Warriors to win their first ever championship. Getting all but one finals MVP vote (VanVleet got the other), Leonard was the clear best player on the floor for most if not all of the finals and the playoffs in general. As great as DeRozan was, he was never able to make that claim, and that’s necessary to lead a team to a ring. At the end of the day, it might have only been one season, but it was the best season the Raptors ever had. Kawhi gets the spot as the second greatest Raptor of all time.

1. Kyle Lowry, PG, 2012-2020

There may have been some surprises amongst the other four, but all Raptors fans know who has the top spot on lock. Lowry came to Toronto in 2012 and never looked back, becoming a six time all-star during his Raptors tenure. Nobody can forget the pure joy on his face when the Raptors advanced to their first finals, and then again when they won. No Raptor I’ve ever seen can match the tenacity and determination that Lowry plays with, the willingness to lay his body on the line for his team. Kyle truly does do it all. He takes charges, he scores, he sets up teammates, he rebounds, he leads, and most of all, he wins. Lowry is the Raptors all-time leader in assists, steals, total win-shares, and playoff wins. The one constant Raptors fans have always been able to count on in his years in Toronto, Lowry showed again and again he would do anything it takes to win, and especially to win in Toronto. After his best friend (DeMar) got traded for Kawhi, he accepted the move and made it work with Kawhi, and for that reason much of the Raptors success in their championship season should be attributed to him. He stepped aside and allowed Kawhi to become the leading scorer on a team that was truly always his to lead, but knew when he needed to take over. In the closing game of the NBA finals, Lowry scored his team’s first 11 points, and scored 21 in the first half, keeping the Raptors in the game as some of his teammates struggled. It’s Lowry who has been the leader of this team from the DeRozan era to the Kawhi era, and it’s Lowry who we want leading this team until he retires. Kyle Lowry lives and breathes Toronto basketball, and, for the foreseeable future, the title of greatest Raptor of all-time is not up for debate.