Pirates Roundtable: What Are Your Thoughts on Ben Cherington’s Rebuild?

This week, I've been giving my thoughts on the status of the Pirates' organizational building efforts under General Manager Ben Cherington.

On Tuesday, I gave some reasons why I think the Pirates are headed in the right direction. Today, I covered some of the things which have drawn concern for me.

I wanted to get some other opinions on the subject, so I asked John Dreker, Wilbur Miller, and Anthony Murphy for their thoughts on the rebuild under Cherington. Their responses are below, in a bit of a longer Roundtable format.
I am really down the middle with the work of Cherington, with enough question marks to still wonder if they will be able to compete over time -- or it might just be a quick peak around 2024-25. I thought he really missed some opportunities to package ...



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Glad you guys didn’t drink the cool aide and try to put a positive spin on this. The team has a long way to go to become competitive. Will they get there I hope so but I don’t see any budding super stars down in the farm.


BC doesn’t have a strong track record of success to Pittsburgh, so it just seemed like he came to Pittsburgh to try to restore his image and reputation. Given their nearly unlimited resources, BC did the impossible – fail as the GM of the Red Sox. So, I wasn’t a big fan of the hire to begin with – I would have preferred they pursued the second in command in St Louis, Tampa, San Diego, or Houston for example – not a retread. Time will tell. I do recognize that he hands are somewhat tied by Nutting’s refusal to compete and win. But, he still makes some very poor personnel decisions – VanMeter trade, Heineman trade, Tucker over Cruz, etc. On paper, his drafts have looked good – but, they should given where the Pirates have been drafting. International signings have not shown great promise yet – Shalin Polanco is Exhibit A. He has a long way to go to give me any level of confidence.


In my opinion, BC is a lot like NH – very slow to trust and play the Pirates prospects – and instead hang on to tried and failed vets from other organizations far too long. The fact that Bae is still in Indy, while VanMeter and Yoshi are in Pittsburgh is one recent example. Starting the season with Tucker at SS, over Cruz, was indefensible…..and the results were very predictable. Who knows how that decision has impacted Cruz’s psyche this year, in Indy and now in Pittsburgh.


WM really hits the nail on the head with his first paragraph in my opinion. Nicely done.

Jon got me thinking too, regarding his take on years of control. I’ve thought a lot about the issue over the last few months.

To me, i think i now realize that when people laud “years of control”, theyre really only talking about “under-market-value years of control”. Limiting your “control” of a player to 6 or 7 years or whatever is a choice based in not wanting to pay market value for their free agency years in years 8 9 and 10.

I think the more and more i see this stuff, the more i almost view it as a moral issue. If a guy would improve the roster, then it’s probably immoral to not have him in MLB. it’s probably immoral to not pay him the MLB salary that he deserves, let alone the millions that that player could be losing from the super 2 process.

obviously the “smart” thing to do from a penny pinching middle manager’s perspective based on the rules is to suppress these guys’ earnings and service time. but i think i’m coming around more and more to the thought process that this can dip into the realm of immoral.

A guy who belongs on a team on day 1 of a season, but isn’t brought up until June 20th is missing out on a lot. Theyre missing out on potentially millions of future dollars via the super 2/arbitration, and almost more important to these guys who are just getting started making real money, a few hundred thousand dollars of current year salary. Roansy Contreras, for example, will miss out on like $80k during his current demotion (assuming he’s back in early August). For a guy making his very first MLB checks and never got that big signing bonus like a top draft pick, this is a HUGE deal.


Man is this a bad read…these fucking rebuilds have turned our brains into mush.

The only possible manner in which a kid who’s not prepared to succeed against big legauers actually improves a lineup is if you’ve done an abhorrently shitty job of building a big league baseball team.

We’ve somehow forgotten that the minor leagues exist for a reason and the ultimate goal is to win Major League Baseball games.

John’s take is so banal that it shouldn’t even need to be said, and yet it elicits some diatribe about morals.

God I f*cking hate this team.

Last edited 2 months ago by NMR

I also don’t believe in just throwing players in the majors and letting them learn at the top level. Why waste service time when you’re not getting value from them? I don’t understand the people who were willing to give up a year of service time for top prospects in exchange for seeing them in the majors a month or so sooner.
– – – – – –
Sure why give the fan base – the paying customers – anything to watch or cheer for.
Let’s keep everyone in the minors and keep the farm system rankings as high for as long as possible. Let’s keep pointing towards the future. The higher draft pick is most important

We’re the fan base that has already (recently) gone through 20 consecutive losing seasons!!!


You realize that probably 95% of fans do not give a shit about watching some 22 yo kid get his teeth kicked in against big leaguers he’s not prepared to face, right?


If you keep talking about the future, I think the fans want to see it…eventually (see Cruz, Suwinski) even if their teeth are getting kicked in.

What’s the percentage of fans that enjoy Yoshi, VanMeter, Chang, Alford, Tom…night after night?


None! They want to see actual good baseball players. That’s still an option for the franchise!


I agree. But we’re still waiting for that option


I agree with WM when it comes to Cherington building bullpens. Terrible
Also the needed more ‘hits’ like Gamel and way less ‘misses’ like Knapp, Chang, Tom, Alford and VanMeter


I think the Buccos would do better with more stability in the lineup.


I really believe we would be at 500 now if we had better managers at the major league level. I know these players are technically adults but I believe history has shown the professional no nonsense managers win games. I believe traditional hard-nosed baseball like Jim Leyland demanded and executed is still the way to go. I really would pushed hard for someone like Andy Van Slyke to be the manager and get some one like Doug Drabek or Burnett types to be pitching coach. Then buy some really good starting pitching, not necessarily horses like de grom or Sherzer but guys who can give you 6 innings of 1 to 2 run ball most times out. I mean look at the guys in the top 25 in Era. A ton of those guys aren’t household names but you need to sign them to lucrative deals when they hit free agency. Am I living in a dream world, for a pirates fan yes, so all I can do is love the pirates and be miserable and hope that they all step in dog shit and have a few good years like they did from 13 to 15 lol. And I disagree with John on the service time, I could care less about it, play them if they are they best you got, let them figure it out in the majors, not the minors, because the players we play now in spite of the aren’t worth a lick. And if the prospects do take off PAY THEM. It’s like Bae, why not bring him up now, get his feet wet and see how he handles it, what do the pirates have to lose? Time?? Screw time, I want to win now, if he fails at least you tried with a young guy who looks ready for a shot at the show.


I like Wilbur’ take the most. I remember when folks didn’t think Huntington got enough back in trades. Jeez, Most of our trades have brought back nothing of substance with the exception of Bednar, however youndont trade a top end starter for a reliever. Contreras has promise, but we shall see. Not to mention the guys like Kuhl who we let walk. Now all the top draft picks and prospects are struggling. What a disaster.



I was much more hopeful for BenC when he was hired. But when he started making very curious moves I looked back at his success with she Red Sox and realized it was largely built in large ticket FA acquisitions.

That doesn’t mean he can’t succeed with the Pirates, but he has 2 years to put a contending team on the field. Right now, by w-L percentage, he is the worst GM in Pirate history.

That has to change.


Timely discussion as we face the Brewers and AGM Matt Arnold.


not that it matters much, but he’s actually the GM now


Lean a lot more towards Wilbur’s viewpoint than the other two points (which seem to act like we can’t look at anything till five years). This has been pretty piss poor. We’re basically looking at three years (2020-2022) at least they are bottom five teams in baseball. And that’s the plan that’s on target?

I also disagree with John’s take that a drive for 75 is pointless. My issue is not so much signing or acquiring some veterans to hit that win mark, it’s to find an inefficiency with veterans they can exploit.

This org, if they’re going to compete, is going to have to acquire talent externally. It can’t just be homegrown. They’re going to have to find their Burnett, Liriano, etc. And I haven’t seen anything approaching that type of development.

Wilbur Miller

I’ve seen a couple of interesting takes by the FG guys in their chats. One said he didn’t like what they were doing at the major league level. The other said that, between the Orioles and Pirates, he was more optimistic about the Orioles.


So much of it seems about development. If the Bucs happen to run into guys where it “clicks” for them, ok. But I don’t trust this org to develop Jack shit. It’s NH 2.0.


I couldn’t edit this for some reason, but I’d also add that this team will have to crawl before they can walk. They’re not gonna go from 65 wins to 90 in one offseason, with all the prospects maturing at the same time like some phoenix rising from the ashes. It’s likely gonna be from 65 wins this season to 75 in 2023, etc. And that’s the best case scenario.


I agree with the sentiment that we cant really judge anything yet. I see signs for hope and i see signs for frustration, but I could have been made gm with some good players and top draft picks and ended up with an improved farm system. I dont even mind trying to find a cheeky addition on the margins via players like jvm, all the relievers, etc. as that is the cheapest way to even find a role player. August 2 and on for the next calendar year is where i really think we can draw some conclusions


Excellent commentary. Too few elite prospects for me, among other things. John Baker sounds good, but I have no sense whether the development changes are making a difference. I just want playoff baseball again, it’s like nothing else in my sports life. That feels far from a given, if Cherington fails we’re staring down 5,6,7 years of losing and having to start all over again with one of the worst owners in sports. I don’t think any of that will happen, I’m hopeful Cherington will get there, but it sure feels like we’re getting to the point where we need to make some big changes in a short amount of time.


I can comment here but I cannot read the article (


It’s early yet but I really don’t see much of a difference between BC and NH. Both trade for quantity instead of quality, both make confusing dumpster dive pick ups, both ignore obvious team needs……. Funny how our best players are all from other organizations. Doesn’t say much for this team’s player development program. We are still seeing young guys come up and really struggle which happens on all teams, but you also see on other teams non elite prospect guys come up and be useful. I do think we have some interesting guys to build around, but there are plenty of holes that need filled.


it’s nice to see the change in philosophy with player development. catering development to the individual player just makes the most sense imo.

but it’s too early to say whether the development is better regardless. few prospects have taken a step forward this year. and ones that appeared to do so…have backslid recently (peguero, scott, gonzales, etc).

i still lack faith in the mlb coaching staff to get the most out of the players on the roster. i’ve said it before, but hiring haines was one of the most bizarre decisions. it seems like he was just hired because he’s baker’s buddy. with the amount of young hitting prospects the pirates have, they really need to nail that hire. unsurprisingly, the results have been predictable.

as for marin….dunno. has he helped any pitcher improve? i guess you can say crowe…bednar. how much is he responsible for that? who knows

in any instance. i think the pirates are still far off from contending. they still lack elite high end talent in the minors. hopefully someone can blossom from it soon


It will come down to starting pitching, which is where the odds are most stacked against small market teams. You can sign a good pitcher for a big contract, only to watch them implode for a number of reasons. You can trade talent for a good pitcher, and again have them implode. Having a huge pitching contract without productivity can severely hamper a small market team. If we truly have been saving money in the bank the last few years, the smartest route is to actually overpay for a short term contract, but then most good pitchers will take 4 years at X, rather than 2 years at Y, even if X is only a little more than Y. Guaranteed money is what pitchers want. How Cherington addresses the starting pitcher will be the measuring stick for his skills. Huntington went for trading prospects for an ace, and came up empty, and that led to him getting fired. He also relied on Searage magic pixie dust, which worked until it didn’t. It is much too easy to criticize Cherington at this point. How he gets better starting pitching without taking too much organization destroying risk is going to be key over the next 9 months, as there is not enough of ready talent in the minors to fill out a playoff worthy starting pitching rotation for 2023 and probably even 2024.


Huntington came up empty once. We don’t see the playoffs without trades for Burnett, Morton, Locke, Happ. Let alone the astute signings of Liriano, Volquez, etc. Hiw soon we forget. Now we will see how Cherrington handles it. It won’t be easy.


Fair enough, and I am neither pro nor anti Huntington or Cherington. That empty trade was not on the same level as the others, though. He gave up Glasnow, Meadows, and Baz, and basically got nothing in return, it was a huge miss.


I can’t read this article. It cuts off after John drekers first sentence and says subscribe today.
I’m already a member and I’m logged in. Am I missing something?


On a related note, I’m not sure if my subscription expired because I had to replace the credit card that was on file or if there is a glitch. Can you give the steps to check on a subscription and whether a card needs to be updated?


Sobering. But I think we can all agree that whatever this management group is doing, at least we aren’t Cincinnati fans.


Agree with most points made here & think this was a good topic for discussion.

One thing to follow up with on the strike out problems, are we sure that the Pirates minor leaguers in particular are really having more strike outs than most other organizations? From my observations, there’s just more technology & training methods that are advancing pitcher’s velocities & spin rates that hitting is generally getting harder. Curious to know if there’s a way to see where the affiliates rank in K’s in their divisions

Wilbur Miller

Indy: 9th most Ks of 20 teams
Altoona: 9th of 12
Greensboro: 1st of 12
Bradenton: 2nd of 10
FCL: 8th of 16
DSL Black: 3rd of 49
DSL Gold: 8th of 49


So lower levels are a problem. Upper levels, not so much.

Wilbur Miller

Not exactly reassuring. The lower level guys are mainly or entirely products of the current development team, the upper level guys mainly not.


When the Pirates quit trading quality MLB players for some hope and prayer then they have finally turned the corner, until then think nothing much has changed…


Yikes! After reading this, it feels like a long slow walk down death row


Sounds like a good poll question. Pirates future will take the following path:

A. Yellow Brick Road

B. Green Mile

My heart says A, my head says B.

Maybe I’ll be more optimistic on August 1st when guys like JVM, Newman, Tsutsugo, and Marisnick are gone and players like Bae, T Swag, and Captain Bligh are playing regularly.

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