Pittsburgh Pirates: Tracking Ben Cherington’s Rebuild


The Pittsburgh Pirates started a rebuild last offseason. Since then, they have seen many changes in the organization. These changes have been in development, the farm system, much of the staff and throughout the roster. So, how has the rebuild gone thus far?

The complete teardown started with the coaching staff at the Major League level. Before the final game of the 2019 season the Pittsburgh Pirates announced that Clint Hurdle, their manager since 2011, would be fired. A few days later they announced that long time pitching coach Ray Searage would be relieved of his duties as well.

Clearing out the front office was next.

Before the end of October, the Pittsburgh Pirates moved on from team president Frank Coonelly. On October 28th, they made probably the biggest move of their offseason firing general manager Neal Huntington.

Replacing Coonelly would be Travis Williams as the new team president. Then in mid-November, Williams would bring in Ben Cherington as the team’s new general manager. Cherington would quickly fill out the coaching spots that were left empty when the team fired Hurdle and Searage by bringing in Derek Shelton as manager and Oscar Marin as the new pitching coach. Cheringotn also brought in new-age thinkers to the front office like Oz Ocampo and Steve Sanders.

It’s worth going over what Huntington left Cherington to work with. The farm system was far from the worst in baseball, but it could have used some work. Ke’Bryan Hayes, Oneil Cruz and Mitch Keller were three consensus top 100 prospects while first-round picks like Travis Swaggerty and Quinn Priester looked very promising.

Huntington also brought in hard throwing right-hander Tahnaj Thomas in what looked to be a small deal which turned into a top 10 organizational prospect according to FanGraphs. Other notable prospects added by Huntington included Cody Bolton, Mason Martin and JT Brubaker.

On the Major League roster, Cherington was left with one household name in Starling Marte. Both Bryan Reynolds and Kevin Newman had notable rookie campaigns and he was also given starters like Joe Musgrove, Jameson Taillon (although the latter was still recovering from Tommy John surgery) and slugger Josh Bell.

The team was really left with no direction as from 2016-2018, they were a middle of the road team. 2019 was a big wake-up call for the whole Pittsburgh Pirates organization as a huge second half collapse led to many dominoes falling. It quite possibly saved the organization from many more years of mediocre baseball with no bright future.

Cherington’s first big move as GM was trading Marte to the Arizona Diamondbacks for two prospects. Those two were 2019 first-round pick Brennan Malone and highly touted middle infielder Liover Peguero.

In the 2020 draft Cherington selected second baseman Nick Gonzales as his first pick as GM of the Pittsburgh Pirates. He also selected pitcher Carmen Mlodzinski with his first-round compensation pick. Overall, the draft was a success in the eyes of many.

Currently, four of the six picks the Pittsburgh Pirates made rank as top 30 prospects according to FanGraphs, those being the aforementioned Gonzales and Mlodzinski along with pitchers Jared Jones (2nd round) and Nick Garcia (3rd round).

During the deadline, Cherington didn’t make many moves, except trade offseason signee Jarrod Dyson for international bonus slot money which they used to sign Po-Yu Chen. Chen ended the season ranked as the Pirates’ 35th best prospect by FanGraphs, which is really good considering that Dyson only had eight hits in 55 plate appearances with the Pittsburgh Pirates with a 6 OPS+. The hiring of Marin also showed during the 2020 season as Musgrove, Richard Rodriguez, Chris Stratton and Steven Brault had career years.

Cherington’s 2020-2021 offseason has been very active. So far, he has made a handful of positive moves. First, they fired Larry Broadway to bring in John Baker as the new head of player development. He also made a handful of other moves bringing in new names for player development.

His first big trade of the offseason was sending Bell to the Washington Nationals for Eddy Yean and Will Crowe. Yean was the prospect the Pittsburgh Pirates focused on the most. The right-hander ranked as one of the Nats’ top 10 prospects on both FanGraphs and MLB Pipeline. Crowe, although not as highly touted, is an arm that can slide into a rotation spot now. During this year’s international signing period, he signed Shalin Polanco who ranks as one of their top 30 prospects.

After that, Cherington swung a trade that involved Musgrove in a three-team deal involving the Bucs, San Diego Padres and New York Mets. The Pittsburgh Pirates sent Musgrove to the Padres in exchange for a quartet of players including outfielder Hudson Head and pitchers Omar Cruz, Drake Fellows and David Bednar. They also got catching prospect Endy Rodriguez from the Mets.

Head was the headliner (no pun intended) from the Padres. He was the Padres’ third-round pick in 2019, but would likely have been selected much earlier in the draft had it not been for playing quarterback in high school limiting the amount of time scouts got to watch the outfielder.

Cruz has put up outstanding numbers in his 98.1 innings throughout the minors, having allowed just 26 earned runs, a single long ball and striking out 32.5% of all the batters he has faced. He also saw major improvements to his control in 2019.

Bednar, a Pittsburgh native, gives the Pirates a high-upside reliever who can slot into the pen now. Fellows was a 6th round pick by the Friars in 2019. He’s yet to pitch a game yet professionally, but he pitched fairly well throughout college. Rodriguez finally gets the Pittsburgh Pirates their needed young catcher. He’s shown a good mix of high contact, low strikeout high walk rates throughout the minors so far.

Then just days later, he traded Taillon to the New York Yankees for another big package of four prospects. The headliner of this trade was Miguel Yajure, who is seen as a potential top 100 prospect in the near future. He made his MLB debut last year and has improved every year throughout the minors.

During 2019 he only allowed 33 earned runs in 138.2 innings between High-A and Double-A. While Yajure was the headliner, the Pirates got back some other interesting pieces. Infielder Maikol Escotto and outfielder Canaan Smith performed very well at the Dominican Summer League and A-Ball in 2019. The fourth piece was Roansy Contreras, who has proved he is a solid pitcher at every level of the minors so far.

Right now, the Pittsburgh Pirates have a much improved farm system. According to FanGraphs, they have six top 100 prospects at the end of the 2020 season. Two of those prospects were names Cherington brought in, that being Gonzales and Peguero. Joining them is Hayes and Cruz, who are consensus top 100 prospects thoughout baseball. The Bucs’ system is considered one of the most improved by MLB Pipeline as well. Some prospects have seen large steps in development like Hayes and Priester. Other prospects like Thomas, Head, Priester, Yajure, Swaggerty and Malone could join them in reaching consensus top-100 status.

What’s more important is that the team now has a direction and plan. There’s been a heavy emphasis on player development. Right now, the front office is trying to get this team ready to compete again by 2023. They’ve already let players like Hayes and Keller get a taste of big league action. During 2021, we may see the arrivals of highly anticipated names like Cruz and Cody Bolton.

There’s still work to be done. The Pittsburgh Pirates finished last in MLB with a 19-41 record in 2020, however, this earned them the number one overall selection in 2021’s draft. They’ll probably finish the 2021 season with a poor record, securing them another high pick. They could also get more prospects to deepen the farm system if they trade pieces like Adam Frazier, Brault and Rodriguez.

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So far, the Pittsburgh Pirates rebuild has gone very well. The new additions to the front office as well as the coaching staff have been positives as reflected in players improving. They’re overall farm system is much deeper than when Cherington took over and now the franchise actually has a much needed direction and plan. Cherington is far from done though and based on the moves he’s made so far, he knows what he’s doing and has put this organization in a position that they can succeed in the near future. If things go right, we may see .500 baseball much sooner than many believe.