The obvious point of these deals, as you mentioned, is to grab security over a potentially outrageous payday in the future. I wonder what the teams in these situations would have been willing to do.

For instance for Braun, would the Brewers have only bought out his arb eligible years for say $20mil? This would still easily set him for life, but let him hit FA on schedule. The question would be whether the Brewers wanted to do something like that…I’d guess they wouldn’t. They have absolutely NO reason to do this deal at all when they can just keep him for 5 more years of indentured servitude for just more than that same price and not risk anything.

I guess what I’m saying is that while he had to give up a lot of money to get this security, I doubt that there was a deal on the table that would give him a requisite amount of security, while still allowing him to maximize all of his FA years. Does that make sense?

the marginal decrease in the value of money—your first $50 million is worth infinitely more than your second $50 million, and anybody for whom the difference would matter is managing their money so poorly that it likely wouldn’t matter how much they had

present value of money—obviously, money now is worth more than money later, and this is even more tangibly true in this case, where the money will be sufficient to last a lifetime. would you rather have more money than you can ever spend NOW, so that you can start acting like a rich person from age 23 on, or wait until you’re 26, spending the next three years on a tighter budget while your teammates live it up, just so that you can have a larger number on your contract?

certainty—obviously, you say it, but, given that these guys are, by signing these contracts, 100% certain to be filthy rich for the rest of their lives, why is there even a reason to discuss the other factors? i’m not even sure that a 2% risk is worthwhile given that the difference in money between the two contracts is practically meaningless (whereas the risk is HUGE).