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A Look Back at Previous Pirates Offseasons Under Ben Cherington



Pittsburgh Pirates, Ben Cherington

It’s been nearly four years since the Pittsburgh Pirates announced the hiring of Ben Cherington as their new general manager.

Since taking over, Cherington has made it a priority to accumulate as much young talent as possible in a large-scale rebuilding effort. Multiple established players have been traded away for younger assets. Additions to the major league club have so far consisted of modest free agent signings and smaller-scale trades.

This coming offseason could look different than what we have seen in the past under Cheington’s guide. The Pirates took a step closer to contention and will likely look to make more impactful additions to the big league roster.

So, how did the Pirates get to where they are now? A lot has to do with the decisions Cherington has made each offseason since taking the reigns.


The first notable move Cherington made as the lead man in the Pirates’ front office was shipping All-Star outfielder and two-time Gold Glove recipient Starling Marte to the Diamondbacks. In return, the Pirates received minor leaguers Liover Peguero and Brennan Malone.

Peguero made his major league debut for the Pirates in 2022, appearing in a single game. He carved out a larger role in 2023 and hit .237 with a .653 in 59 games. Malone has battled injury problems for much of his time in the Pirates’ organization and has yet to advance past Single-A Bradenton.

In the 2019-20 offseason, the Pirates took a modest approach in free agency. Their signings included outfielder Jarrod Dyson, infielder JT Riddle and outfielder Guillermo Heredia to one-year contracts. 

In lesser moves, the Pirates signed catcher Luke Maile, though he never appeared in a game. The first official trade for Cherington was sending pitcher Dario Agrazal to the Tigers for cash.


The following offseason was more active with several notable players getting traded elsewhere as the rebuild hit full-swing.

The winter really began for the Pirates on Christmas Eve, when Josh Bell was traded to the Nationals for Wil Crowe and minor leaguer Eddy Yean. In 91 appearances/26 starts with the Pirates from 2021-23, Crowe was 10-19 with a 5.03 ERA. The Pirates DFA’d him in July. Yean, meanwhile, spent the 2023 season in High-A Greensboro and went 3-4 with a 5.01 ERA.

Up next in the exodus was the deal that sent starter Joe Musgrove to his hometown San Diego Padres. There was another homecoming in that deal, as David Bednar was part of the return from the Friars. Bednar has since established himself as one of the better closing pitchers in baseball and made back-to-back All-Star teams from 2022-23.

The deal was part of a three-team swap in which the Pirates also landed Endy Rodriguez from the Mets. The Pirates are now counting on Rodriguez to be the catcher of the future after he made his big league debut this past season.

In addition to the Bednar and Rodriguez, the Pirates landed Hudson Head, Omar Cruz and Drake Fellows, all of whom are still in the minor leagues.

The final big trade of the 2020-21 offseason saw Jameson Taillon land in New York with the Yankees in exchange for Roansy Contreras, Canaan Smith-Njigba, Miguel Yajure and Maikol Escotto. Contreras was impressive in 2022 but took a step backwards last season. Still, the Pirates are counting on the right-hander to bounce back and become a key piece of the rotation.

Smith-Njigba has only played sparingly in Pittsburgh. Escotto is in the lower levels of the Pirates’ system and Yajure is no longer with the organization.

Looking at additions to the club that winter, the Pirates signed pitchers Tyler Anderson and Trevor Cahill to a one-year contracts. They also acquired relief pitcher Duane Underwood Jr. from the Cubs. The Pirates made two Rule 5 additions in December in pitchers Jose Soriano and Luis Oviedo.


The 2021-22 offseason was a unique one in that there was a lockout that froze the hot stove from the beginning of December through the earlier part of March.

Prior to the lockout, the Pirates signed Jose Quintana, Roberto Perez and re-signed Yoshi Tsutsugo. They also shipped catcher Jacob Stallings to the Marlins for three players — pitchers Zach Thompson and Kyle Nicolas, as well as minor league outfielder Connor Scott.

After the lockout was lifted, the Pirates signed slugger Daniel Vogelbach and reliever Heath Hembree. They then acquired Josh VanMeter from Arizona for minor league pitcher Listher Sosa at the end of March.

Shortly before opening day, the Pirates signed Andrew Knapp to be their backup catcher and reached an agreement with defensive-oriented outfielder Jake Marisnick.


For the first time under Cherington’s command, the Pirates offseason focused primarily on additions last winter.

Of course, the most notable addition was Andrew McCutchen, who returned to the organization on a one-year, $5 million contract.

The first move of the offseason for the Pirates was trading minor league pitcher Jack Hartman to the Rays for Ji Man Choi. The Pirates added another first baseman a few weeks later in Carlos Santana, who signed a one-year deal as a free agent.

The Pirates’ other free agent additions last offseason included Austin Hedges, Vince Velasquez, Jarlín García and Rich Hill. Hill’s $8 million guarantee marks the richest free agent signing to date for Cherington.

Pittsburgh also swung a couple trades that paid dividends for the 2023 club. They acquired Connor Joe from the Rockies for right-hander Nick Garcia and sent former first-rounder Kevin Newman to the Reds for relief pitcher Dauri Moreta.

Cherington was able to find a contributor in the Rule 5 draft last December in Jose Hernandez, who spent the year in the Pirates’ bullpen.

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