The Path Forward for this Pittsburgh Pirates Team

6-29-25 – By Gary Morgan – @garymo2007 on X

I’ve tried to just let everyone go this year for the most part. Pirates fans came into this season mad, and sometimes it’s best to just let the flames die down a bit before tying to refocus.

I mean, I’ve talked baseball and of course told you what I see as out of bounds, like trading Paul Skenes or whatever, but as the National Media sharks start to circle and the all or nothing mentality takes over, I think I have to simply say this is going too far now.

This team isn’t going to go into another rebuild.

I know, you’ve heard “rumors”. I put that in quotes because you really haven’t heard anything like a rumor. You’ve heard that the Pirates have talked to another team. Then you’ve heard that they’ll talk about just about anyone.

That’s all true, but that doesn’t mean they’re open to moving EVERYONE.

This team is 16 games under .500 so leaving things as they are certainly isn’t in play either. Let’s talk this thing through, I think if you think about it with me it might ease your mind about where things are headed.

I’m going to start by talking about some of the conditions, and I’m going to outline 2 different “plans” for moving forward I could see going.

Is Everyone Available?

No. Not everybody is available, but as I say every year, there are only 5-10 teams who feel they have no chance to make a Wild Card at least in 2025, so the pressure to surrender talent is going to always be amped up for those 5-10 teams. The Pirates are of course one of them.

Because Ben Cherington doesn’t like signing free agents to multi-year deals, every single year they have a host of “rentals” for sale. That’s no different this year, and as always they come with varying degrees of value both to the team and to the league.

Paul Skenes isn’t going to be discussed, mostly because simply trying to come up with his value on the market is next to impossible. It’d be like Jeff Bezos putting Amazon up for sale, he might come up with a value, but there also probably isn’t anyone out there who can afford it, and his new wife might be upset if he were to just decide to entirely change their lives.

Aside from him and Andrew McCutchen, I can see the Pirates having a conversation but this is a team looking to add offense, not subtract it.

Taking phone calls, making phone calls, gaining an understanding of what gets offered for certain talents, that’s stuff a team should do 16 games under or over frankly.

So yeah, everyone is available, but that in no way means EVERYONE is going. Their record absolutely shows change is needed, but let’s keep going, I think I’ll make the case that it doesn’t need to be back to square 1. Paul Skenes being here ensures even Bob will know better.

What Will They Allow Cherington to Do?

This is the most interesting question if you ask me.

The draft that so many seem to focus on as it comes to worrying about his influence, well, honestly, you could probably make this pick. With the 6th pick, the Pirates will either select a College pitcher or a High school short stop.

I don’t think you’ll see a college hitter go in the top 10 this year.

The same scouting department that was replaced before last year will make the recommendation this year and I don’t know about you, I like what they picked up last year in the draft, and how they’ve performed early on.

Point is, the last thing I’m worried about with keeping Cherington around right now is the draft, I think they’ll do fine.

What I worry about is him making big trades. Things that effect this team and the path forward for years to come.

That’s why on the surface I feel we’re going to see a lot of rental movement, but I see Bob Nutting pumping the brakes on anything too major.

Like Jason Mackey just said on the Fan the other day, it’s very hard to fathom Cherington returning for another season. I feel this way too, and I can’t see Bob Nutting allowing him to take cards out of the deck for the next hire. At least not too many to recover from.

Despite popular belief, Nutting is not ready to burn it down, just unhappy with how things have progressed as opposed to believing it hasn’t progressed at all.

Why Keep Cherington at All Then?

That’s the big question. What’s the point of keeping a guy you probably don’t trust moving forward? Bob Nutting has said it would be too disruptive to move on in-season. I guess I can see that, but if he’s on his way out and you don’t really want him making any far reaching changes, why not just move on?

Hey, I didn’t say Nutting made sense did I? Changes need to be made and I’d hate to miss an opportunity while waiting for his replacement.

To be completely fair, I probably don’t want an interim GM making those types of deals either. This is kinda why I made a bigger deal of what I thought was a need to fire the GM last offseason and not during this one.

This situation is and will continue to paralyze this franchise.

Now, all that stuff being accepted and acknowledged, lets move on to what I see as the 2 best paths forward for this club given that they’ve chosen to do what they’ve done.

Path Number 1: Reset, Refresh, Recommit

Forget what the Pirates will do, these two options are completely mine. They’re what I would do, not what I think they’ll do.

First, I don’t think the Pirates can afford to trade all of their expiring contract guys, and the main reason is the innings. If they were to move Dennis Santana, David Bednar, and Caleb Ferguson, might leave them in a situation where they have to fill the bullpen with waiver claims, and frankly, for my plan, I’m not looking to feel like the team is somehow worse than they were to make me want to make deals in the first place. This is a facelift, not a face transplant.

I’d pick one or two of them to move. David Bednar is the most valuable, so to me he’s the one that makes the most sense to make sure I’ve moved.

They have some big options they could move, Ke’Bryan Hayes, Mitch Keller, Bailey Falter, and yes, I think some of these have merit. Before the season I suggested if you could find a taker for Hayes you take it. Yeah, you get out of his contract, but that’s not the real reason to do it, instead it’s to make sure you try to get some offense from the 3B position. Specifically more power.

I think it’s hard to imagine Hayes returning his own replacement, so you either are accepting that Triolo, Nunez, Yorke, types can take it over and give you more offense or, you’re accepting you need to go outside and get someone. If you aren’t going to get someone better, you might just want to keep Hayes. If you allot what you spend for Hayes, it’s probably not going to be enough to upgrade the position on the market, he’s cheap.

Keller is interesting because of how much young pitching the Pirates have coming and he does make consequential money. Again, I’m not trying to dump his salary per se, but I am looking to repurpose his dollars into an extension for either Cruz or Skenes. You could also repurpose his salary into that replacement for Hayes I just talked about needing to invest in. He could also return a 3B, SS or LF option, they need all three and what they get back should be MLB ready, at least one component has to be.

If I could swing it, these are the 3 biggest pieces I move this year. Hayes, Keller and Bednar. I’ll package them together, sell them separately, whatever it takes. But if I move all three of these pieces, I expect to return 2 or 3 RIGHT NOW solutions for this roster.

There’s no feasible way to recover and get the arrow pointed up if you move on from 3 players of starting caliber, and yes, Hayes is that too, unless you immediately recoup actual players who you’ll use from the jump. They can grab some prospects in the process, but the main return needs to improve two positions immediately.

I move as many of the rentals aside from those bullpen guys as I can, for just about whatever I can get. If only to force my own hand to bring up the Billy Cook, Nick Yorke, Liover Peguero, Jack Suwinski types and find out if they are or aren’t going to help me.

The extra money I’ve saved from the moves, I use for those extensions or extension I proposed, but if neither are interested, I use it to fill the hole I didn’t get filled from the deals themselves.

More than anything, I trust that Cruz, Reynolds, Gonzales, Horwitz, Davis types all either get back to being themselves, or improve to the point the team will improve behind them.

And finally, I take the offseason very seriously this time. Whatever I can do or have to do to make sure I don’t enter the season with any major holes and some more power, that’s what I’m doing.

Get a new GM in here and let them shuffle, but don’t let them reset the clock. The fans won’t tolerate it, and despite popular belief, neither will the owner.

The truth here is baked into Paul Skenes. You have until 2030, and if you decide to trade off for prospects, I think you’re looking at 2028 or so before they’re becoming MLB regulars with expectation. If you don’t sell off as I’m suggesting here, your prospects come up when ready and improve the team around the edges as opposed to being relied on to be special from the jump.

Path Number 2: Demolish and Start Over

I would not do this. I don’t think it’s necessary first off, and second, you might as well trade Paul Skenes if you do. Since Skenes is the real reason we’re claiming the team should be ready, it would be the opposite of progress.

Yeah, you could return a bunch of guys, but even after firing Cherington, you’ll still be relying on a development system you’ve never believed in to quickly turn around a bunch of kids and win. Hey, maybe they’ll hire a genius, that’s still not a typical occurrence.

I look no farther than the Nationals, mainly because trading Juan Soto years ago is about as close as you can come to an equivalent for trading Skenes, and bluntly, the return they got is probably a bit light.

They have a good young core, but its already been a couple years and they’re already seeing they don’t have enough. There is room for these guys to improve, and they will, but it’ll be 4-5 years from the time they pulled that trade off to the point where they truly compete again.

Just in time to be trying to figure out how to lock up Gore, Abrams and Wood.

The Pirates can’t do this again, because Paul Skenes is the purpose for doing it to begin with. The Pirates won the lottery and instead of taking the winnings, this method would be like trading the winning ticket for 20,000 scratch offs. You won, and now instead of winning, you want to play again.

The only way you could take this path would be to sell off everything and lock up Skenes for like 10 years, but honestly, I doubt he’d buy into the plan.

In other words, maybe stop thinking this is going to be some huge dump deadline, I see no real path forward that’s viable beyond making some hitting vs pitching balancing moves and trying to fill the most obvious holes with more power.

Subscribe to our site, it’s free and all you’ll get from us is a notification when there’s something new to read.