The Toronto Raptors are set to begin their 2026-27 NBA season with a seismic shift, officially welcoming back franchise legend Kawhi Leonard. His return comes after a recent preseason slate that saw the team go 3-2, including a 129-125 loss to the Detroit Pistons on October 16. The Raptors now turn their focus to the regular season opener against the Chicago Bulls at home on October 21.
Leonard, the two-time Finals MVP who led Toronto to its 2019 championship, rejoins a squad hungry for playoff success. The Raptors haven't won a postseason series since 2020. Last season, they finished 46-36 and lost a tough Game 7 in the first round to the Cleveland Cavaliers. Scottie Barnes earned an All-Star nod, while RJ Barrett averaged 24.1 points per game in that series. Leonard's arrival instantly changes the team's ceiling.
Leonard's path back to Canada was unexpected. After leaving in free agency for the Los Angeles Clippers in 2019, his tenure there was marred by injuries and unmet expectations. It ended with an NBA investigation. The league found the Clippers and Leonard guilty of salary-cap circumvention this year. Los Angeles was fined $30 million, lost five first-round picks, and Leonard was personally fined $700,000.
With an extension off the table in L.A., Toronto moved. Raptors executive vice president and general manager Bobby Webster finalized the trade and a two-year extension once the league's probe concluded. It's a major gamble. Leonard is 35 and has dealt with significant knee issues. But the Raptors believe in their medical staff, led by VP of player health Alex McKechnie, who managed Leonard's load masterfully during the 2019 title run.
Head coach Darko Rajaković is expected to start a formidable five: Leonard, Scottie Barnes, RJ Barrett, Immanuel Quickley, and center Jakob Poeltl. That group blends elite two-way talent with youthful athleticism. Leonard is coming off a career-high scoring year, averaging 27.9 points per game. His defensive prowess, even at this stage, upgrades the entire rotation.
The bench looks to Jamal Shead, recently signed to a three-year deal, rookie Ja'Kobe Walter, and last season's All-Rookie second-teamer Collin Murray-Boyles. Veteran forward Kyle Anderson adds savvy. This depth will be tested quickly in a competitive Eastern Conference.
All eyes are on the immediate future. The preseason offered glimpses of both potential and areas to tighten up. After beating the LA Clippers 114-106 on October 10 and the New York Knicks 148-98 on October 13, they dropped two close games to the Knicks (122-120) and Pistons to close their exhibition schedule.
The real test starts now. The season opener against the Chicago Bulls is a chance to make a statement at home. Leonard's integration with Barnes and Barrett will dictate Toronto's early trajectory. The goal is clear: end the playoff series drought and contend in the East. This high-stakes experiment begins Wednesday.
