I still think Pirates fans are far too dismissive of the idea that this team could sign Skenes, they just won’t be giving him a lifetime deal. This team has no chance of competing with Skenes in a UFA deal, but Skenes is so young that he’ll be hitting UFA super early. You could feasibly give him a deal that eats up his arb years and gives you a few UFA years, which still lets Skenes get his mega UFA in his late 20s.
The Pirates could get Skenes signed to a 6-8 year deal at money below $200 million, and based on the Hayes deal, it would likely be a fairly constant $20-$25 million a year rather than going cheap in arb and paying him UFA money after. Those deals have Skenes hitting UFA between 28 and 30, so he’ll still be in line to get his mega deal as a free agent.
If you want to be wildly aggressive and say his arb years are worth $95 million and his UFA worth is $40 million a year, they could make that a 7 year and $175 million deal that is just a flat $25 million a year. Skenes gets a lot of guaranteed money far earlier than he’d get it otherwise while the Pirates are still getting great value out of Skenes. The yearly money there isn’t a huge step up from what Keller is going to be making, and I figure they’d just trade Keller to be able to afford it anyway.
In reality, Skenes getting that guaranteed money up front would lower the amount of money he’d be getting in those years. I think 8 years and $160 million (flat $20 million a year) with an option extension after it could absolutely work, it just takes the Pirates being bold and aggressive for once.