Gary’s Five Pirates Thoughts – Deadline Week

7-28-25 – By Gary Morgan – @garymo2007 on X

This is it, MLB trade deadline week.

This entire thing doesn’t need turned around by Thursday, but if I’m Ben Cherington, I’m probably looking to do my very best to make sure it looks like it’s headed that way.

Something has to give, you either have to make trades involving painful to part with prospects and eat salary, pay for it yourself on the open market, or do relatively nothing but move the guys there really can’t be much question about moving.

Lets Go!

1. Confusion for All

More than any other emotion, confusion has ruled the day during this season, hell, it’s really been since last offseason.

Nobody knows what the state of the GM is, nobody knows what he’ll be allowed to do, or who would determine what his limits might be. It’s hard to imagine Bob Nutting is that brake, nor his Team President Travis Williams, neither of them have baseball decisions like this in their blood or experience base.

It could be Justin Horowitz who they hired away to lead scouting but that would kind of be like keeping a restaurant GM in place and making his 18 year old shift supervisor the final say on anything deemed big.

It’s been a nearly universal assumption that Ben Cherington will be fired this offseason. Bob did this to his GM, and himself. His comments after firing Derek Shelton opened the door for not only potentially moving on from Ben in the offseason, but also rendering him fairly impotent.

At least that’s the cause and effect of his words. Might not have been his intention, probably wasn’t in truth, but he’s also not so much as attempted to clarify or quiet the groundswell.

Which in itself is a message. He may not have intended to create this uncertainty, but he has, and to not change it, or address it, well, let’s just say it has an air of I made your bed, now you must sleep in it.

To the outside world and the fan base, it screams disfunction. To the room, it spawns dark corners of suspicion, thoughts of who’s safe, who isn’t. I’m sure it creates conversation about it potentially being better for a player to be dealt too.

No matter what, these conversations will happen around this time of season, but it’s a lot easier for leadership in the room to squash it if it could be easily pushed off as typical rumors.

The point is, we can blame who we like for the position we’re in. Bob for not spending, Cherington for not spending what he had wisely, scouting, development, go ahead, name them off. Every angle you can think of is part of this state of confusion and all I can say is no matter what small question you’re trying to answer, it’s always going to be at least partially wrong, because you can’t evaluate a damn thing without first running through this gauntlet of things that don’t make sense.

Just like you, the room will go through these paces, and this team that plans to return the vast majority of players from 2025 to 2026 will first have to come to terms with what happened, where they sit and what exactly they still trust with this team.

Look at these quotes from Paul Skenes to Dejan Kovacevic yesterday.

“You know, we can play GM and do all that. But with the deadline coming, obviously, we need to make the team better for next year and, hopefully, put us in a position where we can make some moves in the offseason, too. So that’s kind of what I’m expecting.”

“That’s what I’m hoping. I know that’s what a lot of other guys in this locker room are hoping, ’cause, I think, obviously out on the field, we have some guys who’ve grown this year, who’ve gotten better, and other guys who’ve, you know, probably under-performed a little bit.”

He’d go on to name Oneil Cruz and Nick Gonzales as examples of growth but the point largely, Paul expects this team to get better next year, he expects it to come from moves and more internal growth.

These are things the GM has said, but the importance here is, Paul agrees, even if reading between the lines you can see it might not be backed by a ton of faith.

Nobody can fix this situation but Bob Nutting, and that’s what scares me. They won’t enter a rebuild again, they won’t tear it all down and start over, but they also can’t keep barely doing the minimum and expecting things to improve.

2. Henry Davis

Henry was drafted as a catcher who was going to hit, but potentially would not be able to stick at the position, I don’t think anyone saw coming what Henry has become in 2025.

It’s also not the end of his story.

Every season Henry has come back with a new bag of tricks. This year it was defense.

He can call a game like few are capable, in fact, if you watch the dugout during games, he’s commenting to Joey Bart in between innings about what he’s seeing.

It’s had Don Kelley mention him on days where he didn’t play multiple times and while it doesn’t show up on the stat sheet, it does help the pitching staff, and it is important.

The reason I say his story isn’t over, he knows his offense has to improve. His bat is what brought him to the majors, even as he had no position this short sighted team would allow him to play and now that he’s built himself into a truly great defensive catcher, the hope is that he’ll refocus on offense and see if he can’t at the very least turn himself into a much more well rounded player.

You may have already decided what he is, but the Pirates would be fools to agree with you. They owe their 1:1 selection more than that, and they owe this team playing it out another year with him if only because being built almost entirely on pitching, it might well be the smartest thing they could do is go all in on the defensive benefits regardless of how he comes along offensively.

.250 with 15 homeruns and the kind of defense he plays would be more than sufficient to continue with him, less than that and we’ll have to reconsider. The offensive pedigree outweighs the defensive with this player, so at the very least, we should probably take from what he’s done that he’s very capable of working on a problem and showing progress.

We need progress from him in 2026, and he’s absolutely getting a chance at it.

3. Congested Market for Bednar

Before I start here, I just want to share that I’ve heard some rumblings that the team is at least considering an extension with David. I have no indication of how far along that is or how plausible it might be, only that it’s been broached.

Now, the thing is, David has really turned things around from his disastrous 2024 finish and his equally frightening 2025 start, but he’s also not the only top rated back end reliever said to be on the market.

Jhoan Duran, Ryan Helsley, top that list. Duran has 2 more years of control, Helsley is in his walk year and David of course has 1 year remaining.

There are more than 3 teams out there looking for an arm like this, but these are unquestionably the 3 best available. In order, Helsley will be the cheapest, followed by Bednar and of course Duran.

Now, that’s how it should be. But Ben Cherington according to one Detroit Tigers reporter is asking for a “bananas” package for Bednar. If that’s the case it tends to mean one of two things. 1. They don’t really want to trade him, or 2. They simply have a price in mind and won’t move him if they don’t hit it.

Both can be true at the same time, in fact point number 2 is sometimes the easiest way to express point number 1.

What this approach costs you this time of year. You only have so much, and while there are more than 3 teams who would be in on a player like this, there aren’t more than 3 who would pay for it.

So by all means, set your price, but make sure if someone meets it, you’re actually willing to take it. I’ve heard this was something that cropped up over the past 5 years and it’s had a detrimental effect on who is willing to do business with the Pirates.

More than anything, don’t do anything that prevents you from getting offers, and if indeed you want to make a move here, make the move. Don’t wait for the price to be set. Be the answer someone is looking for and get the job done.

Or, extend him.

Next year, this conversation looks a lot more like the one St. Louis is having with Helsley. A minimal return or a free agent to be for little more than a comp pick.

4. Andrew McCutchen Will Likely be Back

He’ll be back in 2026, of this I have little doubt.

I have no problem with that, he’s a legend here, he’s been productive and frankly, this team is too offensively starved to consider dropping a player who does what Cutch does for 5 million dollars. They simply won’t find that.

I value Andrew’s veteran leadership, but I do question if it’s the right kind of leadership for this team, and what they’re missing.

If they want to bring him back, I get it is what I’m saying, but I don’t think they can lean on him the way they have this year. He’s productive, he’s just not productive enough to script in playing him every day. It’s also becoming clear Bryan Reynolds as a fielder leaves much to be desired, and that may ultimately mean he needs to DH more than play the field.

This team can’t pretend DH is a filled role and prevent themselves from using other players there, or keep them from looking at different options who might have a big stick and a glove that isn’t nearly as rock steady.

So of course, bring him back, but bring him back with a different role. A part time DH, pinch hitter, or even fill in OF here and there, but don’t expect him to carry the weight you ask 25 year olds to carry.

5. 2021 vs 2025

I’m intentionally looking at these two years because 2020 wasn’t a real season, and frankly, because of COVID, Ben Cherington was scarcely able to change anything, much less put his stamp on it.

Now 2021, that was a horse of a different color, and its really when the “rebuild” started in earnest. It’s also key to remember, DH wasn’t universal in 2021, so there’ll be no comparison there.

Position2021 Totals2025 Totals
Catcher.210 AVG, 13 HR, 55 RBI.211 AVG, 6 HR, 29 RBI
First Base.244 AVG, 22 HR, 78 RBI.212 AVG, 9 HR, 43 RBI
Second Base.267 AVG, 10 HR, 48 RBI.260 AVG, 7 HR, 36 RBI
Third Base.242 AVG, 15 HR, 60 RBI.238 AVG, 5 HR, 38 RBI
Shortstop.228 AVG, 9 HR, 45 RBI.248 AVG, 3 HR, 28 RBI
Left Field.251 AVG, 18 HR, 66 RBI.230 AVG, 9 HR, 40 RBI
Center Field.273 AVG, 25 HR, 85 RBI.219 AVG, 17 HR, 42 RBI
Right Field.235 AVG, 20 HR, 70 RBI.226 AVG, 11 HR, 50 RBI
Designated HitterN/A (NL rules pre-2022).248 AVG, 10 HR, 35 RBI

Now, the numbers from 2021 are obviously for full season and 2025 has some time left to make up ground, but which of these positions look to you like they’re on track to surpass?

Look, these weren’t world beaters in 2021. The primary players were Jacob Stallings, Colin Moran, Adam Frazier, Ke’Bryan Hayes, Kevin Newman, Ben Gamel, Bryan Reynolds and Gregory Polanco.

That team too wouldn’t win a championship and it certainly didn’t have this pitching staff, but look at those homerun totals. There are 1, maybe 2 positions where they’ll hit more this year and while there should be room for development along the way, this team has simply not done well in this department.

Power is still in short supply at the top two levels of the minor leagues and the Majors too. No matter what method they use to improve this team, power is going to have to be an ingredient they look for, or this recipe simply isn’t going to be edible.

This is damning product to produce after 5 years of hard work. If that state of confusion we talked about up there sorts itself out with Cherington remaining, I think the first thing I’d like to do is have someone ask, how do you ignore things like this?

This is his best defense.

Stat2021 Pirates2025 Pirates
Wins6139
Losses10158
ERA (Earned Run Avg.)5.083.73
Innings Pitched (IP)1,420.0853.2
Hits Allowed (H)1,419748
Runs Allowed (R)833354
Earned Runs (ER)799379
Home Runs Allowed (HR)21392
Walks (BB)610278
Strikeouts (SO)1,223720
WHIP1.431.20
Opponent AVG.264.234

Again, there is time left for this to change, but I have to say once more, does it look like it’s trending toward 2021 at all? Right.

There’s no denying Cherington has done a job here on the pitching side, but as good as that’s been, the other side has been abysmal and I don’t just mean they haven’t reached the heights we hoped, they’ve actually regressed.

That shouldn’t happen no matter what your method of rebuild.

Stay tuned, it’s going to be a loud week one way or another.

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Published by Gary Morgan

Former contributor for Inside the Pirates an SI Team Channel

4 thoughts on “Gary’s Five Pirates Thoughts – Deadline Week

  1. I believe that Reynolds doesn’t have a bounce back in him and would deal him now, even selling low. I don’t think he gets better next year and that his fall off defensively has happened to his bat as well. I can’t remember seeing a guy at such a young age going from a decent CF to being about unplayable in the field.

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