Although all extension talks surrounding the Toronto Raptors have been clouded by Kawhi Leonard and the massive payday he is slated to get, Jamal Shead’s extension can’t be forgotten. The Raptors front office needs to have extending Shead as priority No. 2 or 3 behind only extending Kawhi Leonard and finalizing the roster.
Since he burst onto the scene as a rookie in the 2023-24 season, Shead has established himself as an integral piece, being the primary source of bench guard play. There’s no rush to sign Shead, and the Raptors can go through the whole restricted free agency process next offseason, but if they believe he’s part of their core, they should pay him now. Not to mention that the sooner they decide to pay him, the less leverage Shead has in negotiations and the more likely Toronto is to land him on a deal that ages like wine.
Landing Shead on a long-term deal in the range of $7 to $11 million annually is realistic and comparable to other backup point guards in the league. It would also create flexibility down the road to move on from Immanuel Quickley if Shead continues to trend upwards.
Paying Shead now can open more doors down the road
Last season, Shead averaged 6.6 points, 1.7 rebounds and 5.4 assists per game while shooting 36.7 percent from the floor and 32.1 percent from three. While the shooting splits weren’t there, his impact defensively was always felt and his playmaking instincts were the best on the team. His ability to get the Raptors into a set and conduct the show any time he was on the court is something the guard room really hasn’t had since Kyle Lowry. With a more talented cast around him in 2026-27 those assist numbers likely will do nothing but get higher and higher and so will his price tag.
Although his shooting splits don’t look great now, they project to improve over time. With Scottie Barnes and Kawhi drawing more attention from opposing defenses, Toronto’s role players are bound to see more open looks than they did last season. Given his playmaking potential, all Shead really needs to do as an undersized guard is shoot in the 41 to 44 percent range from the field and anywhere from 36 to 39 percent from three to be deemed efficient.Â
Let's say down the road the Raptors are in a position where they want to make a big-time play on the trade market, and it requires combining Quickley and Jakob Poeltl’s money. Trades like that would typically be tricky, as most teams wouldn’t have a player they could rely on to slot right in for their starting point guard. But if the Raptors can lock up Shead on a team-friendly deal for years to come, they have a perfect point guard to facilitate and run a star-studded roster.
A lot of the time in the NBA, teams don’t extend players to maintain financial flexibility and keep options open to make trades and extend their championship window. In the Raptors' case with Jamal Shead, extending him would quite literally be a way for them to keep their title-chasing window open for years to come.
At minimum, he is a solid backup guard on a team-friendly deal that can be flexed into trades or kept off the bench. At his highest, he could become one of the league's cheapest starting guards and potentially finally create an easier escape route from Immanuel Quickley’s contract.
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