given the success rate for big money long-term contracts, especially to aging pitchers, the player doesn't have to be irrational at all for this to work out well for the initial team. just because you get such great age 30-32 seasons from a guy that someone's willing to beat the last four years of the deal in place doesn't mean that you still aren't better off letting him go. that said, i do think these opt-outs do favor the players, just only very slightly. i'd much rather give a player one of those instead of additional money if that's what it takes to get the contract signed. A player opting out for a larger contract may not be as bad as the converse of a player being hurt/ineffective and staying the duration of the deal, but that doesn't make it a positive. Losing a player for nothing who was under contract for less than he can get on the open market is definitionally a negative outcome. If your risk tolerance is such that you don't want to pay the player, then you can get *something* in trade if teams are willing to pay more than the remainder of the contract in free agency. EDIT: Just to make sure I'm clear, I'm with you on the second paragraph. I don't overly care if the Cubs give an opt out, especially if it's to a 30 year old SP like Shark or Price. So if giving Samardzija an opt out after 2 years makes it possible to get him for something like 4+team option at 70 instead of a straight 5/90, sign me up. But at the same time, I recognize that opt out has no positive outcomes for the team itself. when evaluated in a vacuum, true. but this isn't a vacuum, and we can't assume that the potential for 20 mil in payroll flexibility is "nothing" to a team 3 years down the line or whatever. the only way to see this as a net negative outcome in every circumstance is to, again, heavily discount the enormous risk of a 7 year contract to a free-agent pitcher. because yes, a player opt out most definitely can have positive outcomes for the team. just because it may not in a potential year 4 in some scenarios, doesn't imply that it cannot be a net positive in years 5-7. or even in year 4, for that matter