Opening The Pirates Window

Ever since a changing of the guard took place in November of 2019, questions and comments surrounding the Pittsburgh Pirates potential return to contention have filled countless social media posts, bulletin board discussions, articles from beat reporters, columns from bloggers and even some of my emails; with the majority eventually trying to nail down a timeline of when the Pirates will be in the playoffs again or at the very least competing in their own division.

I can’t blame anyone for wanting responses to these nearly unanswerable questions, but I can ask them to temper their expectations and trust the process; at least for the time being. General Manager Ben Cherington has been on the job for a little over 16 months at this point in time, has participated in one draft, parts of two international signing periods and is wrapping up his first full off-season with the team after a truncated 60 game season. Have things been great? Obviously not, or Pittsburgh wouldn’t have the 1st overall pick in July’s MLB June Amateur Draft. However, we also can’t act like some parts of this build weren’t absolutely necessary, with other potentially uncomfortable decisions more than likely still to come.

The Pirates as they are currently constructed appear closer to the starting line than they are to any visible finish, but this also doesn’t mean that they can’t get there quicker with rebound years from players like Bryan Reynolds or Kevin Newman, a Gregory Polanco comeback, Mitch Keller finding his groove and Ke’Bryan Hayes continuing to play at or actually anywhere near the level he has so far. These scenarios are far from guaranteed, just like a 2024 rotation that includes Quinn Priester, Cody Bolton, Brennan Malone, Carmen Mlodzinski or insert pretty much any other pitching prospect; from the ones that have already reached the big league to those who have yet to throw their professional strike.

I have personally followed prospects, on an amateur level, since I was around 13 to 14 years old, which for those of you that know me was a long time ago; and for those that don’t it’s about about as long as Adam Frazier has been alive. Does this make me an expert? Absolutely not, but it does give me some perspective on attempted and “successful” rebuilds, as I have seen quite a few, not just the ones or perceived ones from the Pirates, in my day.

So, what will it take for Pittsburgh to have any chance of a successful one, and sometimes more importantly, when might Pirates Fans know this thing they are longing for is real or possibly just another allusion?

The first step includes something I wrote about recently, which is building a strong Minor League System; from top to bottom. The Pirates are on their way in this aspect, but are nowhere near where they need to be, and Cherington knows it. A piece that definitely goes into this as well is evaluation, which is more important to the Pirates than other ball clubs because as we know they can’t really afford to miss.

The next hurdle is developing the talent they do have, along with those they have yet to acquire. Smart and effective drafting, trades, waiver wire pick ups and free agent signings will only get a team so far. People can’t point to Neil Huntington as an example of a poor General Manager, while touting the likes of Priester, Hayes and Cruz, or even Tahnaj Thomas, as the future of the team, without at least giving him some of the credit, but I won’t put up as much of a fight if you question his organizational philosophy in developing players.

Thus far many of the prospects Cherington has acquired fall into a ETA at PNC Park of around 2023-2024, with a few ready to contribute immediately or in the near future. Does this mean the team will achieve the goal of competing, at or around this time? A lot of this depends on development, along with health as evidenced by the unforeseen circumstances surrounding Blake Cederlind and Steven Brault or Jameson Taillon before them; hence the need for depth and competition at all levels of the system.

The next rung on the proverbial ladder to success is retention of at least some of the talent that already exists at the Major League Level; and that is something Cherington has already tried, albeit unsuccessfully for now, just the other day with the offer of a contract extension to Ke’Bryan Hayes. I can almost guarantee this won’t be the last time Young Hayes, and others like him, will be approached with the opportunity to stay with the Pirates on more of a long term basis. Part of this step also includes portions of the previous ones, including development and evaluation because they have a little bit less wiggle room than others in giving out bad contracts; with an overarching theme of Bob Nutting looming in the background, but we’ll get to that very soon.

The final obstacle to obtaining, and hopefully, maintaining success is properly addressing the needs of the team. Even the most well built Major League ball clubs have needs. If this wasn’t true, you wouldn’t see the likes of the Dodgers, Padres, and White Sox acquiring players in the manner we we did this off-season. Not everything can necessarily come from within, which is where Nutting has to make another appearance. At some point Nutting must give Cherington the go ahead to pay for free agents, more expensive trade pieces and to retain at least some talent.

We can argue back and forth, until we are blue in the face, about Bob Nutting’s role in the level of success the Pirates experienced from 2013-2015 to the ultimate demise of the previous front office, the majority of the coaching staff and development department, beginning on the last day of the 2019 season. This exercise in extreme frustration, mixed with reminiscing about and rehashing the past won’t do anyone even the least bit of good. What matters now is the future, or if you want to be a total pessimist, the possibility that parts of recent history could feel slightly all too familiar.

In the end Nutting will have to spend. Maybe, or probably, not as much as Pirates Fans would like him to, but obviously payroll has to go up; and no this doesn’t just include the natural progression of arbitration and addition of players from the minors or conservative free agent signings. I am talking about actually increasing payroll, with no concrete number in mind as to what that it should or could be.

Now to the real crux of this discussion, partially alluded to by me earlier in bringing up the possibility of an allusion, and why I chose to write this piece in the first place, which is people constantly asking me or challenging me to give a realistic time line of the Pirates returning to relevancy, to explain how we will know it is taking too long or is in danger of failing and sometimes most importantly what should be done if the Pirates get to that point.

In my honest and amateur assessment, 2021 is most likely going to be somewhat or a mess at times. Hopefully and realistically not as downright terrible as 2020, but not good either. In 2022 we should definitely start to see improvement, and not just the individual improvements we will be looking for this season. By 2023, or at the latest 2024 we need to see a level of competitiveness that we saw from Pittsburgh in 2011 and 2012, but optimistically without the second half collapses experienced during those campaigns. And in 2025, the Pirates better be one of those teams that people don’t want to see on their schedule.

Of course this loosely laid out timeline can be adjusted for a number of different reasons. However, if we are sitting here in 2026, going into the last year of Ke’Bryan Hayes’ team control pending an extension or other things I don’t want to think about, at the same time as the season is about to begin still asking some of the same questions, the Pirates are in trouble, and Ben Cherington should be as well.

After writing all of this I don’t know if I answered all, or any of the questions, concerns and comments Pirates Fans have asked me to address since Cherington took over pertaining to the team’s current build, nevertheless, hopefully you at least know where I stand.

But enough about the future, let’s live in the near present as the Pittsburgh Pirates season is set to begin in less that a week; and I for one couldn’t be more excited.

Published by Craig W. Toth

Former Contributing Author at, Co-Host of the Bucs in the Basement Podcast and life-long/diehard Pittsburgh Pirates Fan!

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