The Toronto Raptors have built their identity through smart offseason moves, a strategy highlighted by their 2019 NBA championship run. Their recent form shows a 3W-0D-2L record (LWLWW), with their last result a 114-102 loss to the Cleveland Cavaliers on May 3, 2026. This history of savvy transactions proves essential for a franchise that often needs creativity in free agency.
What are the Raptors' best offseason moves?
The Raptors signed Spanish point guard Jose Calderon in 2005 after he went undrafted. He became a foundational piece for seven and a half seasons. Calderon averaged 12.8 points and 8.9 assists per game in 2008-09, setting an NBA single-season record by making 98.1% of his free throws. He helped Toronto reach the playoffs in 2007 and 2008.
A year later, the team signed Anthony Parker in 2006. Parker returned to the NBA after winning back-to-back EuroLeague MVP honors. He immediately became the starting shooting guard and was key to those same playoff appearances. His success paved the way for his replacement, DeMar DeRozan, whom the Raptors drafted in 2009.
How did the Kyle Lowry trade change the franchise?
In the summer of 2012, Toronto acquired Kyle Lowry from the Houston Rockets for Gary Forbes and a first-round pick. Forbes never played another NBA game. Lowry transformed from a serviceable guard into the heart of the franchise. He became the Raptors' all-time leader in assists, triple-doubles, steals, and three-pointers.
His peak came in 2019 when he led the team to its first NBA title. Lowry retired on a one-day contract this offseason, and the Raptors plan to retire his No. 7 jersey during the 2026-27 season. You can explore more franchise legends on our [squad](/squad) history page.
Why was the Kawhi Leonard trade so important?
The 2018 trade for Kawhi Leonard remains the biggest deal in Raptors history. It shook the entire basketball world. Toronto sent DeMar DeRozan, Jakob Poeltl, and a protected first-round pick to the San Antonio Spurs for Leonard and Danny Green. This was a classic high-risk, high-reward move.
Leonard delivered one legendary season, culminating in the 2019 championship. His iconic shot against the Philadelphia 76ers in the second round is etched in NBA playoff lore. The trade demonstrated the front office's willingness to gamble everything for a title, and it paid off perfectly.
What does this history mean for the Raptors now?
Looking at the current [standings](/standings), the Raptors' blueprint is clear. They must continue identifying undervalued talent and making bold trades. The Calderon and Parker signings show the value of international scouting. The Lowry and Leonard trades prove that a single transaction can redefine a decade.
The team's recent 3W-2L form indicates a need for new foundational moves. History suggests they won't rely on big-name free agents. Instead, they'll likely seek the next hidden gem or orchestrate a surprising trade. Their past success provides a clear model for future team building.
