2022--The Year We Move Up for a QB

Wilson's cap hit would cripple this team.
You seem to forget that the team that trades for a player does not inherit the cap hit of the player's prorated signing bonus. The team that trades the player away retains it... so subtract $13M from each of Wilson's cap hits starting in 2022 (if such a trade were to happen).

If it happens, Wilson's 2022 cap hit would become $24M to his new team... and $27M in 2023.

Going back to Winston, if cut, his voided years total of $4.5M would come due when he is cut... so the cap hit delta in 2022 would be a total of $28.5M... so your statement above may be accurate after all.