You can structure it however you want internally. Set aside 25M a year for the first 5 years then you "pay him" 3/11 the next 3(Actually less than that due to the interest you've accrued over the first 5 years.) So... if you have a 35 year old player at the beginning of this deal, you'd rather be on the hook for an additional $11M for that player's age 41-43 seasons rather than being done paying him after age 40? May I ask why? If I think a player is worth 20M in his age 40 season(assume you're overpaying in the last couple years for a bargain in the first couple), I have a hard time imagining not being worth 11M over the following 3. I believe the point is that you're taking on additional risk when the player is most likely to be worthless. I'll stand by my statement that there are circumstances in which I'd rather be on the hook for 5/125 than 8/136. Just look at it like this: after three seasons of Soriano's deal, would you rather have 2/50 remaining or the 5/90 we're stuck with? I'd sure love for him to be gone after two more years and would pay the extra $7M per year to make it so. 2/50 vs. 5/90 isn't the question. You can't just erase the extra money that would have already been paid out to him. Re: "Most likely to be worthless" The point is you wouldn't sign a guy to that kind of money who is most likely to be worthless. Yes, I concede that I'd rather sign Aaron Miles to 5/125 than 8/136, but that's really Kyleing up the question.