Ben Cherington's challenge: Build Pirates into a winner while sustaining strong farm system

When asked about the progress the Pittsburgh Pirates have made under his direction, general manager Ben Cherington painted a picture that was — quite literally — worth almost a thousand words.

Nine hundred sixty-one, to be exact.

Cherington started his soliloquy Friday by touching on a farm system whose talent depth ranks among baseball’s upper echelon, with five top-100 prospects despite the graduation of shortstop Oneil Cruz and right-handed pitcher Roansy Contreras from prospect status this season. Baseball America ranks the Pirates No. 9 and MLB Pipeline at No. 7.

“The benefit we have in baseball operations is that we get to be part of all the conversations that are happening inside the organization that are harder to see,” Cherington said. “We’re so energized by the work, and I really do believe we’re making progress in a lot of ways that isn’t showing up — it’s not going to show up publicly — but will help lead us to success.”

That can be viewed as a deflection of the Pirates’ abysmal record at the major-league level, where they had the worst record in baseball in 2020, lost 101 games last season and are in last place in the NL Central again. It’s also evidence of Cherington’s design to rebuild the Pirates through the amateur draft and international signings and developing those prospects into major-league players.

MLB Pipeline released its midseason prospect rankings last week, and the Pirates have five players ranked in their top 100. That includes four former first-round picks — catcher Henry Davis (No. 20), shortstop Termarr Johnson (No. 30), right-hander Quinn Priester (No. 47) and second baseman Nick Gonzales (No. 99) — and one player acquired by Cherington through a trade, shortstop Liover Peguero (No. 65).

With three consecutive last-place finishes in the NL Central and the possibility of a fourth, Cherington knows preaching patience to Pirates fans is a hard sell. He has been forthright from the start that he wasn’t seeking a quick fix but rather build a winner from within that can experience sustained success.

“We want to win on a level where it’s going to help us get into October and deep in October. No shortcuts to that, but we believe we’re making progress. We need to make more,” Cherington said.

“The thing is about baseball, there’s no sort of blueprint that you can look up to sort of tell you what a rebuild is supposed to look like — exactly what you do and how long is it supposed to take and all that because every situation is so different. Every team’s circumstances are so different. The players that are in place are so different: where they are, how many you have. Every situation is so different. So no team can be compared to another, I don’t believe, but we do look at all the teams that have gone through something like this and we try to learn what we can.”

If there is a team with a similar market size that the Pirates can use as a model, however, it would be the Baltimore Orioles. After losing in the 2016 AL wild card, the Orioles went 75-87 in 2017, the same record as the Pirates. Baltimore then endured three seasons with at least 108 losses from 2018-21 and had top-five picks in the MLB Draft for four consecutive years, including two No. 1 overall selections.

The Orioles promoted baseball’s No. 1 prospect, catcher Adley Rutschman, to the majors this season and still rank as the best farm system. They have six top-100 prospects, including the top position player and No. 1 overall in shortstop/third baseman Gunnar Henderson and the top pitcher and No. 4 overall in right-hander Grayson Rodriguez.

Baltimore (63-58) entered Tuesday 2½ games out of wild-card contention, knowing that more help is on the way in the next year or so. The Pirates are trying to build something similar, even if Cherington isn’t following the same blueprint of Baltimore general manager Mike Elias.

“I think the common themes are you need a lot of good players,” Cherington said. “It takes some time to get those a lot of good players, and then even after you have them, in a lot of cases, if they’re young players, they’ve got to go through a transition. Good young players don’t always show up in the big leagues on Day 1 and start helping you win.

“That’s our aim, is just continue to get as many as we can and then pour into their development. We believe that’s what we’re doing, and we’ll stay after that. We want to get to more winning as fast as we possibly can, but we remind ourselves that comes through really good work every day and not through trying to find shortcuts.”

MLB.com writer Jonathan Mayo, who compiled the Pirates’ top 30 prospects for MLB Pipeline, credits Cherington for building a combination of high-end talent and organizational depth. Fifteen of MLB Pipeline’s top 20 Pirates prospects and 19 of the top 30 have been acquired by Cherington, with 11 through the draft, seven through trades and an international signing in outfielder Shalin Polanco.

“What’s made the Pirates so interesting is that up and down there’s interesting players. The guys who don’t make the top 30 are still interesting,” Mayo said. “When you have depth, not everyone has to live up to expectations. If one of the top 100 guys doesn’t live up to what we thought, they have other guys who are going to end up being better than we expected. That’s what makes for a really good farm system.”

Now the onus is on Cherington and his baseball operations staff to develop that farm system so it produces major league players while continuing to replenish the prospect pool so that it becomes cyclical. That was the failure of his Pirates predecessor, Neal Huntington, who had the top farm system in 2014 but failed to make the playoffs again after a three-year wild-card run from 2013-15.

“Even Ben would say this: Having the best farm system, you don’t get a trophy for that,” Mayo said. “It’s about getting players to the big leagues who help you win games. That’s going to be the measuring stick, and that’s where the complaints come from.

“What people recognize, especially in a market like Pittsburgh, is it’s very hard to compete and maintain a strong farm system at the same time. The (Tampa Bay) Rays may be the only organization that has figured out how to do both at the same time. The previous regime had a strong farm system, then used it to get players to the big leagues and for trades. Then they made the playoffs and the window closed. It is a very challenging thing to do both, with limited resources, at the same time. That is the challenge Ben Cherington now faces: Can he do that?”

That’s a question that might require another thousand words.