I dunno.
A) He kind of is a f***ing idiot, or at least the type of person to be blinded by how much he loves himself
If he gambles on himself a bit and it pays off he could not only make much more money but he could go down in history
I actually don't think a team is going to pay him quite as much as 5/$175. I think he's looking at $150 max on a traditional deal.
Let's say he signs the deal I envision and then in 2022 he pitches 280 innings with 25 wins, 330 strikeouts, and another Cy Young, along with an MVP. How much does he get that offseason? I think he would be attracted by the chance to go for it and elevate his historic status.
It's also not like it's a massive, all or nothing gamble, based on the possible contract. If his normal contract right now would be 150-175M, he's only gambling like 50-75M.