A good faith contract extension Pirates can at least offer Paul Skenes right now

If you’re the Pirates, there’s no mystery about the first move of the winter. You pick up the phone, call Paul Skenes’ camp, and put something on the table that says two things at once: we recognize exactly how special you are, and we’re willing to pay ahead of time to prove it. 

After a 2025 that bent the sport around him - 10–10 with a 1.97 ERA, 216 strikeouts, a 0.95 WHIP, an MLB-best 2.36 FIP, and a Pitcher of the Year already on the shelf - Skenes isn’t just the presumptive NL Cy Young; he’s a franchise-defining arm at the beginning of his arc. That’s not a normal negotiation. That’s an inflection point for how Pittsburgh intends to compete for the next half decade.

Pirates’ best good-faith offer to keep Paul Skenes starts with record arbitration buyouts

That’s why “good faith” has to be more than a slogan. For small-market clubs, extensions aren’t just about cost certainty; they’re culture statements. The Pirates can’t match coastal dollars in open bidding two winters from now, but they absolutely can offer clarity, security, and respect today. The shape of that respect is simple: blow the doors off his arbitration path, then hand him real agency when free-agent years begin.

Pay him like the ace he already is for the next three seasons, then give him player options north of $30 million in the first two free-agent years. Everybody wins, Skenes keeps control of his prime, and the Pirates buy the best shot at keeping an era-defining pitcher in black and gold.

Here’s the framework that fits both sides. Step one: guarantee the three arbitration seasons with record-setting numbers that escalate aggressively. Think something like $14 million, $22 million, and $30 million — figures that reflect Cy Young-level outcomes without waiting on year-to-year hearings. Layer in award escalators (Cy Young win/top-three finish, innings thresholds) that can bump those totals by a few million per year. Add robust injury protections (partial guarantees tied to roster time) so the player’s floor is meaningful and the team’s risk is rational. That’s the “massive amount through arb” that signals Pittsburgh is done nickel-and-diming star talent.

Step two: tack on two player options that sit right where the market is headed. Slot them at $32–$35 million per year for the first two free-agent seasons that follow arbitration, each with a healthy buyout (say $3–$5 million) so the options carry real weight for Skenes. If he wants to chase the mega deal after another dominant season or two, he can decline and walk into free agency with leverage and health on his side. If he wants stability and a clean runway in a city that’s building around him, he can opt in and get elite AAV without waiting.

From the Pirates’ side, the math is clean. You’d be guaranteeing something like 5 years and roughly $100–110 million all-in (depending on escalators and buyouts) for cost certainty through arbitration and a real shot at two free-agent years at fixed AAV. That’s less than what a single winter of open-market bidding for an ace can run and far more credible than hoping to “bridge” with one-year arb wins. It stabilizes payroll planning, tells the clubhouse the front office is serious, and, most importantly, keeps Skenes in a Pirates uniform long enough for the rest of the young core to stack competitive windows together.

Will it keep him forever? Probably not, and that’s okay. The point of a good-faith extension isn’t to trap a star; it’s to align incentives so both sides can win. For Pittsburgh, this structure buys time, buys trust, and buys October chances while Skenes is at the height of his powers. For Skenes, it front-loads earnings, protects downside, and preserves the right to re-set the market on his terms.