The Toronto Raptors have had their share of highs and lows to in the first quarter of the 21st century, but they've had a superstar on their team for the vast majority of that time. RotoWire took our best stab at determining the best starting five of the last 25 years for the team.
A few things to note on the criteria before we dive in: we took a holistic approach, considering the player's stats, awards and overall impact on the franchise. Also, though positions have become more fluid in the modern game, we chose the traditional two guards, two forwards and one center lineup to determine our team.
Toronto Raptors All-Quarter Century Team Members
Kyle Lowry (2012 to 2021)
Kyle Lowry was the floor general for the Raptors throughout their success in the 2010s and had the prototypical profile of a franchise point guard. He posted standout seasons in multiple statistical areas in his nine-year tenure as a Raptor, accounting for three of the team's top single-season totals in assists and once in steals. Those statistical exploits were rewarded by six All-Star berths and one All-NBA team honor.
However, his true meaning to the team came from his toughness and longevity. He ranks second all-time in franchise history in games (601) and minutes played (20,813) and he also played key a complementary role to Kawhi Leonard on the way to Toronto's only NBA Championship in the 2018-2019 season. In 2024-25 he was still plugging away with the Philadelphia 76ers at age 38, though his props at NBA betting sites have not held as much value.
DeMar DeRozan (2009 to 2018)
DeMar DeRozan paired with Lowry for a number of excellent seasons throughout the 2010s and is the franchise's all-time leader in most offensive scoring categories as well as games and minutes played. Despite now playing nearly half of his career seasons with franchises other than Toronto, when the modern NBA fan thinks of the Raptors, DeRozan is undoubtedly one of the first names to come to mind. Four of his six All-Star seasons came with the team, as did two of his three All -NBA selections.
Unfortunately, he was unable to help deliver Toronto's only championship, as he was the key player sent to the Spurs in the trade that landed Kawhi Leonard in Toronto. Despite the somewhat sour ending, DeRozan is rightfully considered one of the most ionic players to call Toronto home in the last 25 years. In 2024-25, he played 77 games with the Sacramento Kings at age 35, still one to watch for sports betting apps customers.
Vince Carter (2000 to 2005)
Despite spending only half of the time of Lowry and DeRozan with the Raptors, Vince Carter made his mark with iconic dunks during game action, at the 2000 All-Star weekend (when he represented Toronto) and even at the Olympics. His second and third pro seasons particularly stand out in franchise history. The forward's numbers in the 1999-2000 season are still single-season franchise records in points (2,107), 2-point field goals made (693) asd field goals made per game (10.2); in the following season he set the franchise mark for points per game (27.6).
Kawhi Leonard (2018 to 2019)
The forward was something of a mercenary in Toronto, brought in as a known rental while swapping places with the beloved DeRozan. Kawhi Leonard's time with the Raptors could be remembered very poorly in an alternate universe, but his one campaign with the team will always be a part of franchise history as he was the best player in the team's only NBA Championship season. In particular, his play during the entirety of Toronto's run to the Larry O'Brien Trophy stands out. In the Eastern Conference semifinals, he averaged a whopping 34.7 points per game and converted one of the most iconic shots in recent playoff history with his dramatic game-winning shot over Joel Embiid in Game 7 against Philadelphia as time expired.
In the NBA Finals, he had no trouble going toe-to-toe with Stephen Curry and Draymond Green by delivering 28.5 points per game with 3.2 combined steals and blocks. He took home the Finals MVP for his troubles. Then of course, there is THAT shot to eliminate the 76ers:
Chris Bosh (2003 to 2010)
The center's relationship and this standing with the Raptors is likely the most complicated of this list because he departed in 2010 and, more important, became a part of the "Big Three" in Miami. The two sides have since mended fences, and that's a positive thing given everything that Chris Bosh accomplished in Toronto. Another complicating factor for Bosh's legacy is the Raptors' lack of team-level success when he was on the roster. They had only one winning season between 2003 and 2010 -- they also finished 41-41 in one campaign -- and never advanced out of the first round of the playoffs. Nevertheless, Bosh is the all-time franchise leader in key defensive stats such as blocks and rebounds, and he was also an All-Star in five of his seven seasons with the team.
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