You can get a Cy Young pitcher through his age-31 season for $8M a year, or save some money and have to match someone else's $20M/year offer 2 seasons down the road. What possible argument could there be for not signing him now? Sign him now, and with his Health/Makeup hope he wants to re-up with you after the deal you offer him today expires. Try to save money on bench players and middle relievers, not staff aces. Patience has an effect, but not nearly enough to take any chance that he'll change his tune to wanting to test the market.