If I was Scott Harris, this is what I would offer Skubal. First, let's say that a conventional contract isn't going to get it done, because anything the Tigers offer in the form of "8 years, $400M", Boras will just prefer to wait.
Skubal's needs right now are: (1) Set yourself up for life, assuming your career ends early, and (2) worry like crazy that you'll get injured during 2026 and not get anything. Skubal has already had 3 major injuries in his career, this is clearly on his mind.
I would offer something like: 3 years, $60M per year (notably including 2026), with 4 player options: $20M for each of the next two seasons, and $15M for each of the subsequent two.
Here's how I would sell it:
1. You're getting a $~55M raise over what you would otherwise get in 2026. That's real money in your pocket right away.
2. You eliminate all the risk that you get hurt during 2026, or even just have a bad year.
3. Nobody else is likely to give you $60 for 2027 or 2028, so you are putting another $30-$40 million in your pocket early, that you'll never see otherwise.
4. If all goes well, and you pitch like you know you can, then you can skip out on your options, and go for a bigger contract in 2029. You've already made nearly $100M more than you would have in the first three years, and salaries will be higher in 3 years for you to negotiate. If you are great, this is your maximum upside.
5. If things don't go well - maybe 2028 is bad year or whatever, you have great downside protection. And if you rebound later in your career, you can always get out of the contract in any year and go for the open market. It's like having a floor for every year, but no ceiling.
6. If you get injured and never play again, you've got $250M guaranteed.
I don't know if Skubal would go for that, but it's not unappealing.
For the Tigers of course, the downside is they get stuck with Skubal if he gets hurt, or just busts early. But the total damage is a lot less than if you give him the normal ascending contract. And if he's really great, he'll walk early - but you are probably getting his best years.
Michael