Summary
The former undrafted point guard out of Wichita State is in for a big payday, and could cause a real tough decision for the Raptors, who are trying to save as much cap space as possible for a run at superstars in 2021. VanVleet had some massive moments for the Raptors on the way to their first ever championship in 2019.
 
VanVleet continued that strong play this season, showing he can operate on-ball or off-ball. On defense, VanVleet is strong enough and fights hard enough to guard bigger guards, giving his team flexibility to play him at either guard spot.
 
VanVleet will also be 26 years old next summer, so there will be somewhat of a concern about how much more he will improve. While it's unlikely VanVleet takes that next leap into a borderline All-Star, the former undrafted guard out of Wichita has been proving doubters wrong his entire career, and could continue to take strides to become an elite guard.
 
Cap Considerations
VanVleet will be an unrestricted free agent with a $17.8 million cap hold and full Bird rights, so the Raptors will have no restrictions on re-signing him. However, signing him to a large multi-year deal will cut into their cap space for 2021. If VanVleet is brought back by the Raptors on a multi-year contract, they could benefit from frontloading his contract, as it could give them additional flexibility in the future.
 
Since VanVleet will demand a starting salary above the full Non-Taxpayer MLE of $9.3 million, only teams with cap space will be able to sign VanVleet. If VanVleet and an over-the-cap team have mutual interest, sign-and-trade options can be explored.