Suppose the FO has crunched all the numbers on a 5-year contract for an over-30 player, and feels like it barely is acceptable. It includes a risk that the player's performance is bad in year 1, another risk that he's what they hoped for in year 1 but drops off the cliff in year 2, and so on and so forth. Lots of combinations, flips of the coin so to speak, adding up to about the value they are offering. Now, add an opt-out, and suppose 2 years later when the opt-out can be exercised that the player does indeed leave. That means, as we're all agreeing, that the team has done very well for itself and should be pleased with the return on investment so far. However, what has this new information, about 2 more years of performance, done to the computation of risks going forward? Almost certainly, it means that the risk of a sudden decline to worthlessness in year 3 has become reduced greatly, ditto the succeeding years. But the team doesn't get to reap the benefits of these flips of the coin. The player has walked. Those "good" coin flips were part of the original computation. Conversely if the player doesn't walk, the universe of outcomes relating to the remaining risks for years 3-5, respectively, have gone upward from the initial estimates. Because, if he doesn't walk, something bad has happened in years 1-2. All the "bad" coin flips remain on the club's debit sheet. The risk doesn't remain static. It changes as you see the actual outcomes. That's the flaw in the argument. It is the essence of the "heads I win, tails you lose" game, to the player's advantage. I have a hard time believing it's only a small difference in dollars. He can't earn less than $126M now, but if he does well for two years and the market goes nuts in some way (or just normalizes to what he thought he'd get), he could receive a lot more. And it leaves essentially unchanged the odds of the Cubs having to work around dead money, while reducing the positive value they potentially can receive from a mutually guaranteed contract instead. It helps the player, it costs the team. It probably puts the Cubs contract as an actuarial equivalent to, say, what a normal guaranteed $140M contract would bring him - close to what was originally forecast.