Ben Cherington’s Challenge: Make Pirates a Winner While Maintaining a Strong Farming System |

Asked about the progress the Pittsburgh Pirates have made under his leadership, general manager Ben Cherington painted a picture that was worth – literally – almost a thousand words.

Nine hundred sixty-one, to be exact.

Cherington began his soliloquy Friday by addressing a farm system whose depth of talent ranks among the upper echelons of baseball, with five prospects in the top 100 despite the exit of shortstop Oneil Cruz and right-handed pitcher Roansy Contreras from the prospect status this season. Baseball America ranks the Pirates No. 9 and MLB Pipeline will release its midseason organizational rankings on Tuesday.

“The advantage we have in baseball operations is that we can 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 truly believe we’re making progress in many areas that aren’t showing – it won’t be showing publicly – but will help us succeed.”

This can be seen as a deviation from 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 again in last place in NL Central. It’s also evidence of Cherington’s design to rebuild the Pirates through the amateur draft and international signings and develop 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 — wide receiver Henry Davis (No. 20), stoppage -short Termarr Johnson (#30), right-hander Quinn Priester (#47) and second baseman Nick Gonzales (#99) – and a player acquired by Cherington through a trade, shortstop Liover Peguero (No. 65).

With the last three consecutive NL Central spots and the possibility of a fourth, Cherington knows preaching patience to Pirates fans is a tough sell. It was clear from the start that he was not looking for a quick fix, but rather to build a winner from within who can achieve lasting success.

“We want to win at a level where it helps us get into October and deep into October. No shortcuts for this, but we believe we are making progress. We need to do more,” Cherington said.

“The problem is baseball, there’s no kind of blueprint you can look up to somehow tell you what a rebuild is supposed to look like – exactly what you’re doing and how long is it supposed to be. take and all because every situation is so different. Every team’s circumstances are so different. The players 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 think, but we look at all the teams that have been through something like this and we try to learn what we can.”

If there’s a team with a similar market size that the Pirates can use as a model, 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 to 2021 and was a top-five pick in the MLB draft for four straight years, including two No. 1 overall picks.

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 prospects in the top 100, including top player and No. 1 overall shortstop/third baseman Gunnar Henderson and top pitcher and No. 4 overall right-hander Grayson Rodriguez.

Baltimore (63-58) entered Monday 2 1/2 games out of wildcard contention, knowing more help is on the way over the next year. The Pirates are trying to build something similar, although Cherington isn’t following the same plan as Baltimore general manager Mike Elias.

“I think the common themes are that you need a lot of good players,” Cherington said. “It takes a while to sign these many good players, and even after you have them, in many cases, if they are young players, they have 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 goal, it’s just to keep getting as many as we can and then help develop them. We believe that’s what we’re doing and we’ll stay after that. We want to win more too. as fast as possible, but we remember that it comes through doing really good work every day and not trying to find shortcuts. writer Jonathan Mayo, who compiled the Pirates’ top 30 prospects for MLB Pipeline, credits Cherington with building a combination of top-notch talent and organizational depth. Fifteen of the MLB Pipeline Pirates’ top 20 prospects and 19 of the top 30 have been acquired by Cherington, including 11 in the draft, seven via trades and an international signing of outfielder Shalin Polanco.

“What makes the Pirates so interesting is that there are interesting players from top to bottom. Guys that aren’t in the top 30 are always 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, there are other guys who will end up by being better than we expected. That’s what makes a very good agricultural system.

Now, it’s up to Cherington and his baseball operations staff to grow that farming system so it produces major league players while continuing to replenish the prospect pool so it becomes cyclical. It was the failure of his Pirates predecessor, Neal Huntington, who had the best farming system in 2014 but failed to make the playoffs after a three-year run from 2013 to 2015.

“Even Ben would say this: having the best farm system, you don’t get a trophy for that,” Mayo said. “It’s about bringing players into the big leagues that help you win games. That will be the yardstick, and that’s where the complaints come from.

“What people recognize, especially in a market like Pittsburgh, is that it’s very difficult to be competitive and maintain a strong agricultural system at the same time. The (Tampa Bay) Rays are perhaps the only organization that has figured out how to do both at the same time. The previous regime had a strong farming system, then used it to get players into the major leagues and for trades. Then they made the playoffs and the window closed. It is very difficult to do both, with limited resources, at the same time. This is the challenge Ben Cherington now faces: can he do this?

This is a question that could take a thousand more words.

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