The Player Perspective
For players, the option is about providing themselves a safety net for earnings to protect them against a collapse in their market value. To that end, so does a guaranteed year or more tacked on to the end of the deal. What makes the player option so ideal for the player is that if he is able to improve upon his market value then he is able to option out and benefit from that increase in value. Past examples of successful option outs include J.D. Drew, Alex Rodriguez, and Zack Greinke. Past examples of successful option acceptance include Jorge De La Rosa, Brian Wilson, and Dan Haren.
To carry this forward with a concrete example, let's look at Justin Upton who our BORAS model pegged at a 5/85 deal. From our past use of a comp model (which thinks the BORAS model is underpaying Upton by 28 MM), we had projected three general paths for him:
That translated to these cumulative values:
Let us assume the general framework the player and club is considered is a 7/151 contract, which happens to be the Mean expected value during this time frame. So the question is where on each of these generalized track would Upton want the ability to reenter the free agent market? Can he find a sweet spot that would enable him to make his true value or even more? That largely depends on what the team might consider in its interest.
The Team Perspective
From the team perspective, the issue is about not being saddled with responsibility for the worst case scenario. Again, we will use the three tracks to consider where it makes sense for the club to agree to an option out. From our perspective, this is done by considering the probability of value in the Mean and Best cases evening out with the losses potentially accrued. With a 7/151 contract, the worst track results in a loss of 51.9 MM. There are no points along the way for the club to come close to that value. The greatest probable gain is 30.2 MM after the final season of the contract.
Are there any lengths of contract where it would work? Yes, roughly. A 4/85 deal could have an opt out any year of that deal. A 5/106 deal would make sense to allow an opt out after four seasons.
How much less would Upton need to lower his annual earning in order to have an option out make sense with a seven year contract?
7/142; option after six years
7/137; option after five years
7/134; option after four years
7/127; option after three years
7/124; option after two years
7/116; option after one year
Bringing the Two Sides Together
Let us say that the starting point is a 7/151 contract. How much should Upton expect to make over the remainder of his career? Depending on his performance, BORAS (adjusted to make it think 7/151 is the expected deal) thinks he will earn somewhere between 155 and 230 MM over the course of his career with a 7/151 deal. With the suggested salary structure and Upton's projected career marks, there are really only two points at which he might expect to benefit from an opt out: after Year 1 where if he excels he stands to sign another seven year contract with a 1 MM AAV raise or after year 6 where he stand to make a million less (20.6 MM), but have that converted into a four year deal. The first option increases his total potential earnings to 233 MM, a 3 MM increase. The second path puts him in line for a 236 MM payday, a 6 MM increase.
When you put it all together, the deal that makes most sense for the club and for Upton together would be a seven year deal with a player option for that seventh year. The first year option would simply be cost prohibitive. For the seventh year option, Upton has that 6 MM buffer which would put the break even point at 145 MM. One might think there is wiggle room in there for both sides. For the club, it matters little and for Upton it might make him feel more comfortable in having a say over when he chooses to go into free agency.
All in all, this exercise proved not to be as thrilling as I was hoping it would be. Even Upton's most optimistic likely career path did not show much reason for him to opt out. I think the question is slightly more complex than what I show here. There is value to having control over your own future and when you decide to look for employment elsewhere. Some players enjoy that control and one would think there is value in it. Would Upton think that having a four year opt out was worth 17 MM? Maybe. It is not an ungodly sum and maybe, just maybe, he is quite unique and performs at a much higher level justifying a larger pay day. Or maybe it is worth 17 MM to be able to leaving flailing team in search for a more successful franchise. That sort of thing, I cannot measure.