If they're both still dealing after '22, their price tag will have skyrocketed by then. If you're going to do it, I'd rather not wait. I think I'd try to do something like 3/39 after '21 to buy out the remaining arby years for both. With two team options at 19M for '25 and 22M for '26, with 3M buyouts for each, for a total of 45M guaranteed over their arby years and a potential of 5/80. This sets both up for life, and reduces our risk. If they tank, we aren't committed past the 45M. If they're still elite, we still have 2 more years control, and if we didn't want to pay the options they'd be highly valued trade assets. If they weren't interested in a structure like that or something similar I'd probably just ride it out in arbitration. Possible that either or both would rather ride it out til free agency and go for Gerrit Cole type money and if they wanted to roll the dice on that it would certainly be their prerogative.