Since their franchise debut in 1995, the Toronto Raptors have grown from an expansion curiosity into a franchise with a championship banner and a clear place in NBA history. They delivered Canada’s first NBA title in 2019, defeating the Golden State Warriors in six games to claim the franchise’s lone championship.
The years around that run established the Raptors as one of the league’s most consistent teams. Toronto reached the playoffs in seven straight seasons from 2013–14 through the title year and then again in the 2019–20 campaign, when they finished 53–19 and advanced to the Eastern Conference semifinals. That stretch changed expectations around the franchise, both locally and for people interested in sports betting online in Canada.
Recent seasons have been more uneven, but the Raptors have remained competitive. After a 2020–21 season in Tampa and a brief reset, they returned to the playoffs in 2021–22 before falling in the first round. They missed the postseason for the next three years, but entered mid-January of the 2025–26 season at 24–17, well-positioned in the top half of the Eastern Conference and back in the mix to return to playoff basketball.
Raptors Legends Through the Years
The Raptors’ rise has been powered by a core of players who helped lift the franchise from expansion struggles to regular contention. Their legacies span different eras, but each left a distinct mark on the organization’s identity and success.
Kyle Lowry
Kyle Lowry is widely regarded as the greatest Raptor of all time and the face of the 2010s era in Toronto. Acquired in 2012, he became the emotional center of the franchise, blending toughness, leadership, and a relentless competitive edge that reshaped the team’s culture.
Lowry made six All-Star appearances as a Raptor and played a central role in the 2019 title run, pairing his playmaking with timely scoring and charges that swung momentum in big games. By the time he left in 2021, he held franchise records in several major categories, including assists, steals, and three-pointers, and ranked near the top in games played and win shares. A potential one-day contract to retire as a Raptor has long been discussed and would fit the bond between Lowry and the fan base.
Kawhi Leonard
Kawhi Leonard spent just one season in Toronto, but his impact was historic. Acquired in the 2018 offseason, Leonard delivered one of the most memorable single-year playoff runs in recent NBA history, capped by his four-bounce buzzer-beater against the Philadelphia 76ers in the second round and a dominant Finals performance against Golden State.
Leonard averaged over 26 points per game in the 2018–19 regular season and elevated his play in the postseason, where he repeatedly took on the toughest defensive assignments while serving as the Raptors’ primary scorer. He became only the second player to win Finals MVP in both conferences and cemented himself as the central figure of the Raptors’ championship story, despite departing for the Los Angeles Clippers that summer.
DeMar DeRozan
DeMar DeRozan represents the bridge from the Chris Bosh era to the Lowry championship core. Drafted ninth overall in 2009, DeRozan steadily grew into a perennial All-Star and one of the league’s most reliable mid-range scorers, helping the Raptors shed their reputation as an afterthought in the East.
DeRozan was instrumental in leading Toronto to its first-ever Eastern Conference finals appearance in 2016. His scoring outbursts and ability to get to the free-throw line kept the Raptors competitive in multiple playoff runs, and his 52-point game in 2018 placed him among the franchise’s most prolific single-game scorers. The 2018 trade that sent him to the San Antonio Spurs for Leonard was painful for many fans, but it also directly set up the 2019 title. DeRozan later signed with the Chicago Bulls and, more recently, the Sacramento Kings, surpassing 26,000 career points and solidifying his status as one of the most productive scorers of his generation.
Vince Carter
Before DeRozan and Lowry, Vince Carter was the first true superstar to put the Raptors on the global NBA map. Acquired on draft night in 1998, Carter quickly became one of the league’s most electrifying players, combining explosive athleticism with scoring flair that helped drive both ticket sales and national TV exposure for a young franchise.
Carter’s 2000 Slam Dunk Contest performance remains one of the most iconic in league history and has permanently linked his name to the Raptors brand. On the court, he led Toronto to its first playoff series win in 2001 and pushed the eventual conference champion Philadelphia 76ers to seven games in the second round, coming within a single missed buzzer-beater of the conference finals. Though his departure to the New Jersey Nets in 2004 was contentious, time has softened the edges, and he is now widely recognized as a foundational figure who gave the Raptors credibility and attracted a new generation of Canadian basketball fans.
Chris Bosh
Chris Bosh carried the franchise through much of the post-Carter, pre-Lowry period and served as Toronto’s primary star in the mid-2000s. Drafted fourth overall in 2003, Bosh quickly developed into an All-Star-caliber power forward, anchoring the Raptors’ frontcourt with his versatility, face-up scoring, and rebounding.
Bosh led Toronto to division titles and back-to-back playoff appearances in 2007 and 2008, earning multiple All-Star nods during his seven seasons with the team. He left in 2010 to join the Miami Heat, where he won two championships as part of the “Big Three,” but his Raptors tenure laid the groundwork for later success by stabilizing the franchise after Carter’s exit. His contributions during that era often get overshadowed by later achievements, yet his production and professionalism during a transitional period made him a key pillar in Raptors history.
The Raptors’ Evolving Legacy
From Carter’s high-flying early days to Bosh’s steady star turn, DeRozan’s loyalty, Lowry’s leadershi,p and Leonard’s one-year title run, the Raptors’ legacy is defined by distinct eras that built on one another. Each of these players helped shift expectations, turning Toronto from an expansion project into a respected franchise capable of both sustained contention and championship success.
As the 2025–26 team pushes to re-establish itself as a regular playoff presence, it does so on the foundation laid by those stars. Their impact is visible in the fan base’s expectations, the franchise’s reputation, and the belief that another deep run is always within reach when the right core comes together.
