Dam8610

Split evenly between the teams, it's about $24 million per year per team.

Which is why you structure the deal to make it stupid for the player to opt out before year 6, even if they have the option prior to that.

Not that much in a 3 year period, especially because I think a bid of 10/410, especially structured like that, would be well above market in the first place.

So the market is going to go from 3/160 for a 26 year old superstar to 3/200 for a 29 year old superstar in 3 years? Doubtful.

Why would a player look at it from any perspective other than opt out to opt out? The money on the deal from years 4-6 would be $155 million for 3 years, at which point, he'd have another opt out. Your argument seems to be based on the presumption that either the player is stupid or the teams are stupid, which is why it doesn't make much sense. Stop hyperventilating over a 3rd year opt out. Structured correctly, it's fine to put in a contract.

No, I'm saying at age 29, he'd be stupid to opt out of 3/155 for 7/280, because in the long run, he'll end up with less money on 7/280. You think a 32 year old Harper or Machado, continuing their current performance, wouldn't be able to get $125 million or more on the open market? Or that a 33 year old Harper or Machado wouldn't be able to get $85 million on the open market? Because that's basically your argument. I think Harper or Machado would be more willing to bet on themselves than you are.

You're either lying or not doing math correctly. The final 4 years of a 7/280 deal after a 3 year opt out would be ages 32-36, not "all...after age 35". Again, I want him to opt out at 32 or 33.

In fact, since you posted it, let's go 10/410 with opt outs at 3, 6, and 7. 55-55-50-/-55-50-50-/-40-/-25-20-10 So, let's look at year 3, assuming he's produced well. Teams aren't stupid, so he won't be looking at a 10/400 deal at age 29, but for sake of argument, let's say 7/280 is out there. Why would he opt out of 3/155 to get 7/280? He'd be getting over half that money in the first 3 years and could then supplement those earnings at age 32 with a 6/150 deal, which would likely be available at that point, or he could stick with it one more year, get 4/195, then supplement that with a 5/125 deal that would likely be available to him were he performing well at age 33. Any way you look at it, with the exception of teams becoming stupid again, it's stupid for the player to opt out at the age 29 season, and a lot smarter to opt out at age 33, which I want them to do anyway.

Because the estimates for what Harper or Machado might get on the open market are all over the place. I need to know what you're expecting to structure the deal properly. Also, no way in hell I sign your deal if I'm Harper or Machado and there's anything comparable with a year 3 opt out on the table somewhere. That's too little upfront money.

Teams aren't stupid. Nor are players. How about this: you give me a total dollar number and AAV, I'll structure a deal with a year 3 opt out, and you give me a logical reason why he would opt out at year 3. Seem fair?

Nelson Cruz

You frontload it in such a way that years 4-6 are attractive enough to make going back out on the open market look risky. Those will be the cheap, controllable years for a good portion of the core, and the rebuild will have failed if they don't have the fan interest to sustain a high dollar payroll by 2025. So, essentially you're getting the control you want while giving the player the optics they want and not outspending the market by some obscene amount. What's the downside? The minuscule risk of them opting out of what is essentially a 3 year high AAV deal? If smart, calculated risks aren't taken at some point, this rebuild won't be successful.

Why is everyone scared of the year 3 opt out on a deal the Sox should be frontloading? To me the ideal contract structure for the White Sox in pursuing Machado or Harper includes opt outs at years 3 (to get his camp to buy in), 6 (to make him ignore the first opt out), and 7 (which is ideally the one he takes). You then frontload the crap out of the deal to the point that opting out at year 3 might lose them money, opting out at year 6 might make sense for them, but opting out at year 7 makes a ton of sense for them. People keep saying the White Sox will have to pay this huge premium to land one of these guys. I disagree. I think with a creatively structured contract, the White Sox could land either of them at the same AAV and total dollars as any other offer on the market.

I'd put more of that money upfront and add a year 7 opt out (the one I want him to take). Remember, now is when the White Sox have payroll flexibility, they won't at the back end. Here's how I'd structure that: 55-50-50-/-50-50-50-/-45-/-25-15-10

This says loud and clear that if they don't get Machado or Harper, potential sign and flips are the way to go. This gives up too much prospect capital just to possibly compete in 2019. Instead, wait for Arenado, Rendon, and all of the pitching to come available next year.