The Toronto Raptors have never had the easiest road in free agency. That has forced the franchise to find different ways to build, and some of those bets have paid off in a huge way.
The clearest example sits at the center of the team’s lone championship run in 2019, a title that made Toronto the first NBA champion from outside the United States. But long before that trophy arrived, the Raptors were stacking up offseason moves that helped shape the franchise’s identity.
One of the earliest wins came with Jose Calderon. Signed by Toronto in 2005 after going undrafted in 2003, the Spanish guard turned into one of the most underrated point guards in franchise history.
He spent his first 7.5 NBA seasons with the Raptors, helped them reach the playoffs in 2007 and 2008, and put together a standout 2008-09 season by making 98.1% of his free throws, an NBA single-season record at the time. That year, he also averaged 12.8 points and 8.9 assists per game.
Toronto also found value by looking beyond the usual talent pipeline. In the following summer, the Raptors signed Anthony Parker, a shooting guard who had spent three years in the NBA as a fringe player before rebuilding his career overseas in Israel and Italy.
After winning EuroLeague MVP honors in 2005 and 2006, Parker made his way back and immediately stepped into the starting lineup in Toronto. The move helped fuel playoff trips in 2007 and 2008.
When the Raptors took DeMar DeRozan in the 2009 NBA draft, it was seen as a replacement for Parker, who left in free agency that summer and signed a two-year deal with the Cleveland Cavaliers.
Then came the move that changed everything. In the summer of 2012, Toronto traded Gary Forbes and a first-round pick to the Houston Rockets for Kyle Lowry.
Forbes had played 48 games for the Raptors the year before and never appeared in the NBA again. Lowry, meanwhile, became the engine of the franchise, finishing as the Raptors’ all-time leader in assists, triple-doubles, steals and three-point shots.
His rise from dependable point guard to perennial All-Star gave Toronto exactly what it needed, and his biggest moment came in 2019 when he helped deliver the championship.
Lowry recently retired this offseason on a one-day contract with the Raptors, and he is expected to have his No. 7 retired by the organization during the 2026-27 season.
The biggest swing of all came in 2018, when Toronto stunned the league by landing Kawhi Leonard and Danny Green from the San Antonio Spurs in exchange for DeMar DeRozan, Jakob Poeltl and a future first-round pick. The trade ended up powering the 2019 title run, and Leonard was named Finals MVP for the second time in his career. It also could still matter again if Leonard returns to Toronto once the deal with the Los Angeles Clippers becomes official.
In Other News...
Raptors Face A Costly Kawhi Gamble After NBA Punishment
The NBAs punishment of the Clippers has revived an old Raptors what-if, because Toronto is once again tied to the franchises most consequential swing in recent memory. The league handed down the maximum penalties allowed under the Collective Bargaining Agreement after finding salary cap circumvention tied to Kawhi Leonards off-court income opportunities and other violations, a ruling that puts a familiar name back in the center of a costly conversation for the league.
Leonard was fined $700,000, while the fallout also reached beyond the player himself. Former Clippers business manager Dennis Robertson was banned from league activities for five years, and owner Steve Ballmer was suspended for one year from all league and team activities, underscoring how serious the league viewed the case and why it now hangs over any discussion of how the Leonard era might have unfolded differently. [Read more 🡒]
Kyle Lowry Is Giving Raptors Fans A Rare Toronto Reunion
Toronto is setting up a familiar scene for Kyle Lowry again, this time with a public celebration at Maple Leaf Square on Sept. 19. The free event, called Kyles Block Party, will give Raptors fans a chance to mark his career with the club through merchandise, giveaways and a rotating cast of special guests, with Lowry himself expected to be part of the day.
The gathering also fits into a longer runway to one of the franchises biggest honors for a former star. Lowrys No. 7 is scheduled to go up to the rafters on Jan. 10, 2027, when Toronto hosts the 76ers, and this falls reunion looks like an early chance for fans to reconnect with one of the defining players of the Raptors modern era. [Read more 🡒]