Depends on just what it costs for him to insure against injury.
But he could have *locked in* 100mil+. Current net worth estimated at 2 mil.
https://www.celebritynetworth.com/richest-athletes/nfl/dak-prescott-net-worth/
That's a big difference. The marginal utility of squeezing an extra 10 or even 20 mil out of Jerry is negligible compared to that *first* 100mil. Also, time is money, and he missed a fat run up in stocks.
If you ignore insurance, it would have been just stupid for him to play games he didn't have to last year. Stupid risk on a mountain of money that dwarfs what he then had.
But if it made sense to do last year with insurance, it certainly makes sense to do this year again, with 33mil in guaranteed franchise money coming.
He and Cooper should make Jerry pay through the nose now, or just play the season on tags while insuring themselves against injury, and then squeeze Jerry again next year.