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

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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.

JOHN DREKER

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 trade pieces and instead went for quantity over quality by getting rid of one player at a time. I saw too many potential relievers and bench players in those returns and not enough upside. He has really added a ton of depth to the point that the back-end of the top 50 prospects in the system is extremely strong/deep, but you can only get so much from those types of players. I’m hoping they will realize the flaw in having too many middle ground prospects, and if they are making future trades, package players, throw in money or middle ground prospects if necessary, but go for quality.

I really like what they did in the 2021 draft and I think it’s a plan they should try to put in place again this year, unless one of the top two draft prospects (Druw Jones or Jackson Holliday) falls to them. The 2020 draft plan was very straight forward (boring) and right now no one from that group is exceeding expectations.

The international side is a bit tougher to gauge because some of the players signed under Cherington were already signing with the Pirates before he was hired, due to the way that side works. I also believe it’s a bit too early to see the full effects of their attempts to improve player development. I give them an A for effort and the game plan, but an incomplete on whether it is actually working or not. That’s something that needs more long-term data attached.

I love how they front-loaded the contract of Ke’Bryan Hayes and it would be nice to do that with some other potential long-term pieces for the right price. Give them money now so you have money to spend through free agency in 2024 to pieces already in place. I’m not 100% confident they will do that (spend money on legit free agents), but I like having the option available.

I don’t mind how they have handled 2022. It was a lost season from the start. I don’t see any upside in getting slightly better short-term players to possibly win 75 games if all goes right. That’s how Dave Littlefield lived his life as a GM and it left no room to actually compete. If you’re spending real money on players, they need to be people who are around long-term. 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. So, I like how they have handled 2022 for the most part in the majors by sticking to the plan.

I really want to see how they handle things going forward before I’m really for or against the build. My focus point is the middle of 2023 for the time that they really need to start showing things. It’s possible that prospects like Mike Burrows, Quinn Priester, Henry Davis, Liover Peguero, possibly Nick Gonzales (and you would hope others), could be showing up in a big wave right around the same time, adding to the pieces already in place. That is when I will really judge the rebuild, in June/July of 2023.

WILBUR MILLER

At this stage of a rebuild, it’s misleading to think you can tell whether it’s on track or not. This is the easy part. All but the most dimwitted GMs – i.e., not Dave Littlefield – can trade for prospects, use high draft picks, and pump up the farm system’s rankings at Baseball America. The hard part is developing prospects, integrating them into the major league team and adding productive veterans. So you’re trying to judge a rebuild on things that haven’t happened yet.

With the caveat that we haven’t reached crunch time yet, I see plenty of reasons not to be optimistic. It’s easy to point to individual problems. Ben Cherington’s top priority, other than protecting Bob Nutting’s profits, was supposedly turning the Pirates’ development system around. If you want to think optimistically about how he’s done, you definitely don’t want to check out the two class-A affiliates this year, or the 2020 draft class, or the system-wide struggles with hitters swinging and missing, and pitchers not throwing strikes. We can’t even look at the 2021 draft because the key players, including the top pick, have hardly played as pros.

But the biggest concern is a much broader one. The strength of the Pirates’ farm system is depth rather than high-end talent. That’s not necessarily fatal, as there are certainly different ways to win. The Cardinals did it for years by carrying a core of big stars. The Rays have done it by loading the roster with solid to good players. If you’re going to win without big producers, you need a front office that shows consistently good judgment about talent, is determined to make the necessary moves in order to avoid having holes in the roster, and that utilizes the talent effectively.

Cherington and Derek Shelton have shown none of these abilities. Cherington’s been extremely inept at building bullpens, showing a preference for waiver-claim relievers whose track records provide no reason whatever for optimism. His choices of veteran role players have been terrible – to take just one example, the trifecta of Andrew Knapp, Jake Marisnick and Josh VanMeter at the end of spring training this year was truly a remarkable run of pointless acquisitions, all the more so because these were obvious needs that Cherington ignored until the end of spring training. The catching situation is a farce.

The determination to build a solid roster — the sense of urgency — has also been absent. Cherington and Shelton have happily tolerated some shockingly bad performances over long periods of time. Bringing back Michael Perez to make another big run at hitting .150 is an example, or letting Gregory Polanco pile up -1.8 fWAR over two years. Or acquiring players like Perez and VanMeter, who’ve never had an above-replacement season. Utilizing the talent on hand isn’t likely to be a strength, either, with a manager who bats Daniel Vogelbach cleanup against left-handed pitchers when he has a career OPS against them of .486. Or who, on multiple occasions, lets Perez bat in critical, late-game situations. Or who’s so rigid in his bullpen usage that he insists on abiding by prearranged “schedules,” or won’t keep a veteran reliever out of important, late-game situations when he’s had a string of failures in those situations.

And then there’s Bob Nutting. The Pirates are going to have to spend money on veteran players to make the rebuild work. Yes, we keep hearing that Nutting will spend the money when the mythical, magical “time is right.” We’ve heard it before.

For the Pirates’ rebuild to succeed, the team is going to need a huge number of good decisions and a high level of determination to win. For that to happen will require a full 180 from the way the team has been run so far by the current front office and manager.

ANTHONY MURPHY

So far, I feel like the first few stages of the rebuild have gone as planned for Ben Cherington and the Pirates. The early stages are always to acquire as much talent in the system as possible — through trades, and the draft. Cherington has certainly done that.

Now as we enter the more difficult stages, there have been openings for criticism as far as what he has done. There have been some head scratching moves made, like the DFA of Luis Oviedo after spending so much effort in keeping him around last year — he was gone just like that.

Now, bigger picture, a lot of this won’t matter because they don’t really impact the long-term plans. Oviedo is struggling in Double-A right now with Cleveland, for example.

This stage is really where a lot of teams slip up at — the development part. Cherington has inserted as much depth in the system as you possibly could in the first couple of years. Now it’s time to put them on the right path.

While there is still half of the season left, you can make a case a lot of players are kind of stagnant right now. Mike Burrows has obviously taken that leap, as did Matt Gorski before his injury, and Ji-Hwan Bae. Outside of that, you can make a case no one is really taking the next step you would hope for on their way to the majors.

Nick Gonzales, the first draft pick of the Cherington era, is out with an injury right now — and when he was healthy didn’t look like the advanced college bat we had hoped when he was taken. But, the jury is still out on him.

There’s also a huge strikeout issue in the system right now that’s impacting almost everyone.

This isn’t a make-or-break year by any means for the front office, and despite the run differential, the major league team is a lot more competitive than you would have thought, even if the record doesn’t show it.

Overall, even if there are some concerns, Cherington seems to have the Pirates on the right path to being a playoff contender very soon, so it seems hard to argue with the bigger picture of things.

What it will come down to is if the front office can put the players coming up into the right position to take that leap from ‘prospect’ to ‘major league regular’.

THIS WEEKEND ON PIRATES PROSPECTS

Williams: The Bob Nutting Paper Company

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

Bradenton Marauders: Three Pitchers Ahead of Game In Changeup Development

Tim Williams
Tim Williams
Tim is the owner, producer, editor, and lead writer of PiratesProspects.com. He has been running Pirates Prospects since 2009, becoming the first new media reporter and outlet covering the Pirates at the MLB level in 2011 and 2012. His work can also be found in Baseball America, where he has been a contributor since 2014 and the Pirates' correspondent since 2019.

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