2. Spurs give up too much future upside for a win-now piece
In trying to keep objectivity here, I first need to preface this by saying OG Anunoby would be the prize in this trade as he's the most naturally talented player of the three involved. That said, I'm not so sure Devin Vassell is going to need much longer to be on a similar level.
Vassell already made a bigger jump from year one to year two than Anunoby did. While it's true he played seven more minutes per game than OG did in his sophomore season, looking at the per 36 and per 100 possessions numbers already show the two aren't that far off from each other.
In a way, I feel like many Spurs fans value Devin as highly as Raptors fans view Anunoby. Is the hype warranted? Other fanbases would probably say no, but they don't really watch these guys play on a daily basis.
Giving up Vassell for Anunoby would be like forwarding the clock, -- giving the Spurs a taller, more polished player with a similar skillset -- something they'd already be getting by just letting him continue to develop (besides maybe the taller part).
Call me crazy after the season OG just had, but I think San Antonio would come to regret letting go of their own high-upside starter quickly in such a trade package. So given what we know about what both sides should be seeking, what does a package look like that could satisfy both sides?