Why It Makes Sense For The Raptors
The Raptors like VanVleet. He has become a big-time contributor along with Kyle Lowry and Pascal Siakam. The only situation where he does not come back could be if they bring in a replacement like Victor Oladipo.
Antetokumnpo was previously mentioned and indirectly, he may be a huge part of this. There have been rumors where VanVleet could land upwards of $23-$25 million on the free agent market. If the Raptors want to pay that price, they would basically be out of the running in the Giannis sweepstakes come 2021.
If they pull off a sign-and-trade for Oladipo, they would have him for one season while leaving the team completely open for 2021. Oladipo would act as a one-year rental, then Toronto would decide what they wanted to do moving forward.
The Raptors could choose to re-sign Oladipo while pursuing Giannis, depending on the price. This is a move that would keep them in the running moving forward.