Williams: After One Season Under Ben Cherington, the Pirates’ Direction Remains Unclear

David: What are we supposed to tell them now? Ok? You’ve dug us quite a hole.
Michael: We tell them the plan, right?
David: There is no plan.
Michael: Here’s what we’re gonna do. The 45 day thing that I outlined, we go with that. Day 45, company saved. Day 44, go. What do we got? We have 15 minutes.
O’Keefe: Excuse me?
Michael: Just whatever comes to mind. Shout it out.
O’Keefe: Who the hell is this guy?
Michael: I am the guy who roused that crowd.
David: Yes.
Michael: Got them on their feet.
David: Yes.
Michael: They were so happy down there.
David: Yes.
Alan: Who cares?

When I started writing about the Pirates, Neal Huntington had a bit of a head start as General Manager.

He was hired in late 2007. He drafted Pedro Alvarez in 2008, breaking the cycle of the Pirates going cheap in the draft, even if Buster Posey would have been the better selection.

The 2009 draft was unorthodox, but at least provided the start of a trend of going heavy on over-slot prep players, which was another deviation from Dave Littlefield’s tenure as the General Manager.

At the Major League level, Huntington showed changes in his first two years, with the boldest move being the Nate McLouth trade in June 2009, dealing away a young player who could help a losing franchise for several other players who eventually helped the Pirates when they returned to being contenders.

There were mistakes made in each of these moves. One thing was clear: The Pirates were heading in a new direction. They had some sort of plan, and it wasn’t just the “Drive for 75” approach of the Littlefield days, which eschewed any focus on prospects and development for the future.

I can’t say when it became obvious that Huntington was a massive change in direction from Littlefield, as I started covering the team during his second season.

What I can say is that we’re at the end of Ben Cherington’s first season with the Pirates, and I’ve yet to see anything that shows how the Pirates will be different under Cherington versus what they saw from Huntington the last few years.

The biggest criticism I had of Huntington in his final years as General Manager was a lack of direction. There was an allergic aversion to the word “rebuilding” and the team constantly held back prospects in favor of veteran players who might help them win in that season.

Cherington took over less than a year ago, and immediately continued the “build not rebuild” line, which is fine, as we’re just using ambiguous words to summarize a plan.

The problem?

The Pirates have yet to show any kind of plan.

Cherington met with reporters yesterday, summarized by Adam Berry at MLB.com, and many of the comments came across like a first-year General Manager.

“Been reminded more than ever this year that it’s about planning and not plans,” Cherington said. “Planning is something that adjusts every day. You just do all the time. If you try to set plans in a year like this, you’re probably going to be redoing them the next year.”

Granted, this was a difficult year to have any concrete plans with the global pandemic altering the sport. Regardless of whether the Pirates are “building” or “rebuilding”, they will need to put a big focus on prospect development, which is difficult when the minors are shut down.

One confusing aspect about this was the news that Larry Broadway has been removed from his role as head of the farm system. Berry noted that there could be more “reorganization” in the baseball operations department.

Why the Pirates waited until now to make these types of moves is the big mystery. You could say that there was no need to make a change prior to now with no minor league season, but then what even factored into the decision to remove Broadway?

I’ve talked with Broadway a lot over the years. The farm system direction was largely overseen by Kyle Stark, but Broadway had some say. He also had some good input. I’d chalk the Pirates’ increased focus on the changeup and off-speed stuff in the lower levels up to Broadway’s direction. Prior to that change (no pun intended), the Pirates were known for going fastball heavy in the lower levels, and producing pitching prospects who needed to develop off-speed stuff once they arrived in the upper levels.

The biggest issue under Huntington was development. The Pirates had talent, but couldn’t get the best of that talent to show up in Pittsburgh. It’s hard to quantify that, and determine how much was due to Stark versus Broadway.

When Cherington kept Broadway at the top of the development system, he gave him a chance. Less than a year later, it appears there will be a new approach to the farm system.

“We’ve talked about, maybe this is an opportunity to start doing some different things for the Pirates, so we’re in the middle of that conversation,” Cherington said. “I would expect there would be some change in the leadership in player development.”

Before Cherington was even hired, I was calling for a revamped look at the front office, and especially the player development system. Prospect development has gotten too big for the outdated approach of one General Manager to oversee an organization and one farm director to oversee every prospect. If the Pirates are moving to a more modern system, that would be a welcome adjustment. The question is, why wait a full year before making the change?

At the end of this season, we don’t have any more answers to the Pirates’ future than we did when Huntington was fired.

Are they out of No Man’s Land? They’re clearly not a team that can contend in 2021, with the upside being that they sneak into a Wild Card spot in an expanded playoff. Will they continue to play the middle ground and make a half-hearted attempt at winning in 2021, rather than focusing on better chances in future years?

Have they caught up to league trends with pitching mechanics and approaches? There have been some positive signs here, but ultimately the pandemic robbed us of a large enough sample size to say anything definitively either way. They’ve definitely shown some changes, but change doesn’t always mean better results, and we’ll have to wait and see what kind of results come next year.

The most important thing is the farm system. We’ve heard all season, including in comments from Cherington, about the lack of talent in the organization. While the talent has been depleted from when the Pirates’ system ranked number one in 2015, it’s still a very talented system, with a lot of toolsy players in the lower levels, and some potential impact guys in the upper levels.

What will make or break Cherington’s tenure is the result of the farm system. We saw this with Huntington. Who knows how far the Pirates go in 2013-15 with better development, and who knows what happens after 2015, for that matter?

Cherington acquired an organization that has Mitch Keller under control through the 2025 season, and Ke’Bryan Hayes under control through the 2026 season. He’s got younger players like Bryan Reynolds and Kevin Newman under control through 2024. He has top prospects like Quinn Priester, Nick Gonzales, Cody Bolton, Tahnaj Thomas, Travis Swaggerty, and others to develop, potentially joining that group.

One wild card is Oneil Cruz, whose future is in the air after his accident last month, which had some reports of alcohol usage. Cherington said that the Pirates have “no reason to believe [Cruz] wouldn’t be available for Spring Training” as a full participant. That shouldn’t be taken as gospel that Cruz is innocent, since the Pirates have a vested interest in Cruz returning to baseball as soon as possible. Reports are all over the place with Cruz, and until the trial, it’s best to wait patiently for the results, rather than projecting Cruz’s future return. We know that Cruz is an impact prospect, who could be a huge asset to the Pirates if he’s developed properly. That fact needs to be compartmentalized out of this situation for the time being until the situation is resolved. The end result is that the Pirates see a benefit if Cruz is able to return to baseball immediately.

I’d imagine we’ll get a better idea of Cherington’s direction during the 2021 season, and maybe even during this offseason. Perhaps the only issue is that the direction the Pirates should be moving in is obvious, and the cagey non-answers about “still learning”, “build versus rebuild”, and “planning versus plans” are not what this organization needs.

Huntington didn’t provide clear answers either, and there was no clarity provided on the field with the organization’s direction or plans. Any Pirates fan fearing that Cherington is just Huntington 2.0 really has very little to ease their concerns, based on the identical wordplay games, and the lack of any real answers to the future direction after one year.

Pirates fans have been looking for the return of a winning team, and a front office that is open and clear about their direction. They’re not getting the latter, which only leaves them clinging to optimistic hope and small sample sized trends for the former.