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. 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. 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. 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.