if this is worded too awkwardly, here's a gross oversimplification to make it clear what i mean if a player would rather sign a 6 year deal for $200M with an opt out after, say, year 3, than a 6 year deal for $300M with no opt out, then the opt out is good for the team. what that dollar valuation is, i have no horsefeathering idea, but it exists. But it seems to me that from the player's side, if they are really really good for the first 3 years, they are going to opt out for more money, and you are likely to lose that awesome player. If they suck, they are NOT going to opt out, and then you're on the hook for the rest of the contract (see: Jason Heyward) It’s exceedingly rare that a players best years will be at the end of their contract. Losing those because your FA did even better than expected at The part of the contract he’s supposed to be good at is a win