Could 2027 Be Paul Skenes’ Last Year With the Pirates?

TGIF, everyone, and happy start to the Major League Baseball offseason.

We have a lot of ground to cover over these next couple months, including the perpetual lockout that's coming up.

But first, let's talk about this winner and what the Pirates have in store.

Every Friday here on Offbeat, we are doing a mailbag where I am answering your questions about the Pirates and Major League Baseball.

If you have a question and would like to be part of next week's episode, leave a comment down here below or leave one at any episode this week.

But we've pulled a couple. We're going to talk about them, including how much longer is Paul Skenes going to be a Pirates?

Good morning and welcome to OffBeat here on North Shore Nine presented by FanDuel.

My name is Alex Stumpf and this is a daily look at your Pittsburgh Pirates.

We're going to start here in the first segment here with questions we got from YouTube.

And the first is from WV Pirate.

Will this be the last year for Paul Skenes, especially if the CBA changes eligibility for free agency?

To tackle the second part of that question first, nothing has been discussed that's publicly known that would greatly alter how free agency would be conducted.

In the last CBA negotiations, the players, excuse me, tried to expand Super 2 and make more players arbitration eligible.

That didn't come to be, it ended up being, higher bonuses and the bonus pool for all pre-ARP players instead.

But there was never really a discuss of, well, you only have to be a free agent or a major leaguer for five years to become a free agent.

I don't see that changing.

The only outcome where I could see that potentially changing is if the players eventually relent on the cap and floor system.

And that's their concession here.

Because I'm a cynic here.

I think the only reason why owners want the cap and floor isn't for competitive balance.

It's to, boost up team values.

And that would be like, well, this is our way to make more money too then.

I don't think that'll happen though.

But that's the only outcome where I think it could happen.

So I still think Paul Skenes will be under team control until he hits six years of major league service time.

He's at three years right now.

But that said, could this be the last year of Paul Skenes in 2027?

There's a timeline where it's yes, in my opinion.

Now I'm going to start this off by saying Paul Skenes has not demanded a trade.

The Pirates are not shopping Paul Skenes.

Paul Skenes is a Pittsburgh Pirate right now.

But there is an outcome where this 2027 team doesn't live up to expectations.

They don't make the postseason.

And maybe they're not even actually particularly good.

Ben Cherington's entering the last year of his contract to BGM.

The Pirates just part ways.

And they start anew with a new guy.

And the new guy, look, whenever Ben Cherington was hired, he was inheriting a team from Neil Huntington, which, in my opinion, wasn't terribly far away from being competitive.

I know they had that really ugly second half, but it was one of those, you fix the culture, you bring in a couple hitters, maybe you can change something.

They rebuilt.

Because that's the most appealing part of this job.

The job security and the ability to build it up in your own image.

And if I was a good GM candidate, for me to consider moving to Pittsburgh, it would be, I need to build this in my own image.

And one of the best pieces you could possibly have as a trade to restock your farm system, to start building the club the way you want it to be built, is Paul Skenes.

If you were to dangle him out as a trade, Chip, man, would that mean a lot.

You would get back a lot.

Even if Skenes doesn't go back to Cy Young mode, and he has a year in 2027 that's very similar to his 2026, where he still struck out 200 batters, he still did a lot of good things.

It just wasn't nearly the same pitcher that he was the two years prior.

Teams would still be like, look, if that's the perceived floor, or even like the 20th percentile outcome, yeah, we'll give a lot.

Because of that ceiling of being the best right-handed pitcher in baseball.

So if the Pirates really do stink in 2027, I would speculate that, yeah, Paul Skenes would be on the trade block.

Now, if they're good, they make the playoffs, yeah, no, he's got to stay here.

It would take so much for the Pirates to make the postseason in 2027, and then Skenes to get traded, even though he would be making a pretty hefty payday by that point.

I don't think there's going to be any outcome in 2028 if the Pirates make the playoffs in 2027, where he's not on the 2028 team.

But if they don't, and they make wholesale changes, I think there's a very distinct possibility that he could be a trade ship.

Garrett Sherwin 3467 asks, why haven't the Pirates tried to change Hank's swing, referring to Henry Davis.

And they've worked on it, both sides.

They've worked on it, they have to keep getting better.

With Henry, there are plenty of reasons why he hasn't panned out in the major leagues so far.

Work ethic is not one.

He works as hard as anyone in baseball.

I don't know if he always focuses on the right things.

I've been steadfast that a big part of his issue is how quickly he gets the barrel of the bat out in front.

He gets it too far out in front.

It leads to hard contact on the left field line.

This is conversations I've had with analysts, with scouts.

My eye test only confirms it.

That is my opinion.

And there was a portion late last year where he was working on his legs.

And in my opinion, it's like, that's not what the issue is.

I don't think that's what the issue is.

He works hard, but you have to be collaborative.

You have to be willing to go focus on different parts.

Like, it was before 2025.

I remember talking to him about his off-season.

And he said that he just hit balls off of a machine all winter.

And he wasn't working with anyone.

And in my head, I'm like, man, that's not the answer.

That's not the answer.

If nothing else, there need to be people in your life, people that you trust, that you can collaborate with.

And he's gotten better at that, but it's still not enough.

So, to answer your question, they have worked on his swing.

There have been.

he's more upright.

I think that's a step in the right direction, his stances.

I think he's more collaborative.

I think maybe he's trending in the right direction, but there's still a long way to go.

In my opinion.

And this is going to be, honestly, the last winner where we can even entertain the kiddie breakout offensively.

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So, we're going to Twitter for the rest of these questions.

And we're going to start with Chris, CQ, CQuinn0919, who asks, who gets the next extension?

And I'm going to preface this by saying the Pirates have talked extensions with guys in the past.

Like, they have in the past kicked the tires with O'Neal, but, like, nothing is imminent right now.

And Konnor Griffin, I think, was the big whale last year.

Obviously got done.

Huge deal.

He's locked up.

I think there are a couple that would make sense.

I wouldn't hate, the last time the Pirates had a flamethrower, a lefty reliever, they extended him.

So, I would consider that with, like, Mesa Montgomery.

Just buy in right now.

They didn't do it with David Ben-Nar, and they never really discussed it with David Ben-Nar.

But Montgomery, I think, profiles better as an extension candidate.

Just because, he throws harder, he has the starter track record with the arm, history.

I think you have to consider that.

I don't know what an extension would look like.

But if you just want to buy out the RBers, maybe a year of free agency, get that certainty.

And if he does end up being as good as we think he could possibly be, get him for a bargain.

I think that would be a big swing right there.

I don't think anything's going to happen with Odeo Cruz at this point.

I think they're too late in the game.

I wouldn't hate, kicking the tires on Esmerlyn Valdez, just to see if he'll take a long-term, get the money up front type deal.

this is just speculation on my part for these.

But, yeah, I think Montgomery would be, in my opinion, the best candidate here.

Just to get him locked up.

Because you have Reynolds, you have, I don't know if any of these starting pitchers outside of Bubba Chandler, or even in a point where you could, negotiate.

A lot of them are going into arbitration.

It's going to be tough.

I think I look more on the position player and reliever side.

Chip Flip 8 asks, How long is the lockout suspected to last, according to experts?

We don't know for sure.

That's the best we can say.

Both sides seem steadfast going into it.

My guess, my guess is we are going to be talking about Pittsburgh Pirates baseball in April.

I don't know if those are games.

I don't know if those are spring training games.

I don't know if those are people going to spring training.

But I think in April, we're going to be talking about it because I don't think, I'm calling BS on the owners saying they'd be willing to punt a season.

I don't believe that.

I think whenever these guys start missing some time and missing some paychecks, the discussion is going to change.

But yeah, we don't have a real answer here.

Some might say a whole year.

But that is my opinion.

I don't know if I would consider myself an expert on the matter.

And finally, Terry Phoenix 4S, will the Pirates or other teams be looking to avoid one-year deals for the usual rentals in anticipation of a potential lockout?

Wondering how much off-season strategy changes with that looming over?

And it's a really good question.

Because the players in 2020 in particular, during the COVID year, their one hardline stance was, we are getting a full year of service time, no matter what.

So each day of that season ended up being prorated to like two point whatever days of service time.

Because the players did not want to set a precedent of losing service time.

I have to imagine that's going to be the case this time around, too.

And if that's the case, you can make an argument that if you signed a player to a one-year deal in November and the season actually does get lost, that player is now a free agent.

So I don't, I still think there are going to be good candidates for one-year deals.

I think a lot of this market is going to move fast, especially guys on multi-year deals.

There are also going to be players who aren't going to sign by the lockout.

They didn't last time.

And those type of players maybe do tend to be a little more one-year candidate, prove it, prove it candidate type guys.

But I think if the right opportunity came along and a player took a one-year deal beforehand, or desired a one-year deal beforehand, I think they would still be able to get it.

It's going to be interesting for the Pirates in particular who have signed one free agent to a multi-year deal since the start of the 2017 calendar year, and that was Ryan O'Hearn last winter.

Thank you so much for listening to OffBeat here on North Shore Nine, presented by FanDuel.

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We will talk again on Monday.

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