So Adam McKay specificially (creator of Winning Time, Vice, and The Big Short) has never gotten permissions for his previous works, he stated this about Winning Time:
"Of course, this isn’t McKay’s first time capturing real historical figures onscreen. The “Vice” and “Big Short” director has plenty of experience dealing with pushback: “We know the drill at this point,” McKay said. “You get the fact-checkers, you check with the lawyers, and there are
very clear parameters: You’re never going to create
character-defining moments; it’s always going to be within the realm of the true story.”
So, it might just be that they are well-versed enough in the legal loopholes to get it through without the subjects approval. It would certainly be better than a whitewashed version that Vince would authorize himself.