Jason Mackey: If the Pirates actually want to talk contract extension with Paul Skenes, the first step is simple

Jason Mackey, Pittsburgh Post-Gazette on Aug 12, 2025

Published in Baseball

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PITTSBURGH — Discussions of contract extensions weirdly defined much of last week for Pittsburgh sports fans — Paul Skenes during the early portion, then Cam Heyward and Chris Boswell later on.

Vastly different cases, obviously.

But also ones bound by missing some key points.

For the football guys, they're mostly on the player side, the fact that Heyward just did this a year ago, as well as the Steelers' longstanding policy of not extending anyone other than quarterbacks with multiple years left.

With Skenes, a radio overreaction sparked the latest round of speculation. It started when 93.7 The Fan's Andrew Fillipponi asked Pirates pregame/postgame host Dan Zangrilli whether the organization has "tried to make some headway" on a contract extension with Skenes.

"Yes," Zangrilli answered before explaining the obvious difficulties in getting something done. That somehow morphed into active discussions between the two sides, which isn't true.

Has it been broached? Not in a grandiose or formal way, but yeah, it's come up. He's a generational talent. They've maintained a desire — however fanciful here — to have those discussions, and it's more a routine way of operating than anything.

I'm pretty sure they'd like to extend Skenes.

I'd like to hit the Powerball.

Neither has a strong chance of happening.

Fact is, this entire topic is a waste of time until the Pirates start winning, no matter how many creative contracts are posited across social media.

Skenes is one of the most intense competitors I've ever seen. It governs everything he does. One of the few comparisons I'd make involves Sidney Crosby. But we need to cool it unless the Pirates enjoy a 2013-15 redux.

Which, of course, elicits a different — and far bigger — discussion about what they're doing with general manager Ben Cherington, as well as what should or will happen this offseason.

I'll get there.

For now, it would be foolish for Skenes to sacrifice free agency time until the Pirates are making the playoffs and executing a more successful team-building strategy.

It's nothing against Pittsburgh, mind you.

Skenes genuinely likes it here and actually believes the Pirates can win. I swear. I've heard it. It's why I believed every word Skenes told our Noah Hiles while the Pirates were at Coors Field following the MLB trade deadline.

"Hopefully [the moves] created some space for us to acquire some bats in the offseason," said Skenes, who also mentioned the growth of younger teammates while several times emphasizing that "it's all about winning" to Hiles.

"Obviously time will tell if it's a good deadline or not, but I think we're in a position to build as a team, as an organization. We just gotta go out there and do it."

Skenes isn't wrong. There's ample work ahead.

It's why the Pirates must — for the billionth time — move on from Cherington and entrust someone else to find external solutions aimed at improving the offense.

If the scenario for a potential new GM involved not rebuilding (Pirates owner Bob Nutting's desire) ... but spending money around Skenes, Mitch Keller, Bubba Chandler and the rest of what has turned out to be a pretty good pitching staff, cool.

I just don't trust Cherington to find the bats.

The Pirates need more power from third base, perhaps a right-handed complement to Spencer Horwitz at first, and a shortstop with an OPS well north of Isiah Kiner-Falefa's .639, among other things.

If a new GM inherits Don Kelly (likely) and a stop sign on rebuilding, but he does get to spend some money to construct a better roster, one filled with a few actual major league hitters, again, I don't hate the idea.

If there was ever a time for Nutting to hike payroll and show he's serious about winning, the time is now. Until then, skepticism is more than fair.

But to change the conversation surrounding the team and genuinely start one with Skenes, there's no other option. Have to make winning No. 1.

Until then, we're wasting our time.

The Pirates can't and won't pay Skenes enough to convince him to forfeit free-agent years, and the "extension" concoctions that only run through arbitration — theoretically locking in a lower rate — make zero sense. The organization assumes sizable risk while having the best-case scenario be an undermined discount over Skenes' arbitration awards.

I don't blame Skenes. If anything, I respect the heck out of it. Let winning dictate. Screw the idea of potentially making a little more now. It's all about a championship.

It's why the only real game-changer involves the Pirates fixing their problems — first with the GM and then with the offensively challenged roster, creating that next winning era with Skenes front and center.

Hey, we can hope.

But given the Pirates' recent shortcomings and the fact that Cherington somehow remains employed, I'm not holding my breath or tweeting some fictitious contract and convincing myself it could happen.

Have to win first.