Pirates’ Offseason Moves From Past 5 Years; Not Much to Rave About

Ben Cherington is now in his sixth offseason as general manager of the Pittsburgh Pirates.

The Pirates hired Cherington to replace ousted GM Neal Huntington following the 2019 season. For much of his tenure since his hire, Cherington oversaw a complete rebuild.

Trying to rebuild the Pirates was the logical and obvious choice at the time. A 69-93 finish in a disastrous 2019 season encapsulated the organizational woes since the Pirates’  last playoff appearance in 2015.

But here we are in year six of the new regime, and while the Pirates are adding to the roster, not much has changed results-wise as of yet.

The Pirates still shy away from the free agent market. Since Cherington took over following the 2019 season, they have yet to sign a free agent to a guaranteed multi-year contract. Think about that for a second. Five and a half offseasons and zero free agents signed beyond the season they joined the club.

Anyway, here’s what the Pirates have done in each offseason under Cherington.

2019-20

Cherington’s first offseason consisted of marginal free agent signing and one trade to help the rebuilding efforts.

The Pirates traded Starling Marte along with cash considerations to the Diamondbacks for Liover Peguero, Brennan Malone and international bonus space. In free agency, Pittsburgh signed catcher Luke Maile, infielder JT Riddle and outfielders Guillermo Heredia and Jarrod Dyson.

If you remember, Dyson responded with, “ain’t too much out there right now,” when asked by a member of the media why he signed with the Pirates. That might be a good way of summarizing the organization’s standing in the eyes of free agents and their difficulties in landing players.

2020-21

In Cherington’s second offseason, he really started to tear things down.

The Pirates made several significant trades with Josh Bell, Joe Musgrove and Jameson Taillon all getting shipped out of Pittsburgh. Of the three trades, only one netted anything of real value. Musgrove was traded to the Padres as part of a three-team trade with the Mets. In that deal, the Pirates received David Bednar from the Padres and Endy Rodríguez from New York.

The most notable free agent singing that offseason was Tyler Anderson, who served as a valuable innings-eater in Pittsburgh and really revitalized his career.

The other offseason additions that winter included trades for relievers Nik Turley and Duane Underwood Jr. and outfielder Dustin Fowler. In free agency, the Pirates signed Trevor Cahill in addition to Anderson.

2021-22

New year, similar story. The Pirates were still rebuilding at this point but not to the extent of the previous offseason.

The Pirates dealt catcher Jacob Stallings to the Marlins for a trio of players including Kyle Nicolas, who looks primed to be a big component of the bullpen in 2025 and beyond.

The Pirates made another trade shortly before Opening Day, acquiring Josh VanMeter from the Arizona Diamondbacks for a prospect. That one didn’t turn out so well.

In free agency, the Pirates were more active than the previous two winters but the additions didn’t provide much. They re-signed Yoshi Tsutsugo and added Daniel Vogelbach, Roberto Pérez, Heath Hembree, Andrew Knapp and Jake Marisnick.

The prize of the free agent additions, however, was left-handed starter Jose Quintana, who was not only effective while in Pittsburgh, but netted them Johan Oviedo in a deadline deal with the Cardinals.

2022-23

Finally, the Pirates (kind of) went for it.

Cherington was active making additions to the Pirates’ roster two years ago, but the results were a mixed bag. Ji-Man Choi was acquired from the Rays, Dauri Moreta was acquired from the Reds, Connor Joe was acquired from the Rockies and Mark Mathias was acquired from the Rangers. Some good, some bad.

The Pirates’ free agent signings consisted of Carlos Santana (good), Rich Hill (not bad), Vince Velasquez (promising before injury), Austin Hedges (not a fan favorite) and Jarlín García (injured and didn’t pitch).

And of course, the big news was the return of Andrew McCutchen, who signed a one-year deal with the Pirates after five seasons away.

2023-24

The Pirates were fresh off of a 14-win improvement from 2022 to 2023 and were trying to make another jump towards contention in 2024. Instead, the Pirates ended up with the exact same 76-86 record that they did the previous season.

Two left-handed pitchers were added to the starting rotation. The Pirates made a trade for Marco Gonzales and signed veteran Martín Pérez. Gonzales was injured for most of the season and Pérez was traded midseason for salary relief.

To help the lineup, McCutchen returned again. Rowdy Tellez was signed to a one-year deal to play first base and Edward Olivares was acquired from Kansas City.

The Pirates also made their biggest free agent signing to date under Cherington as Aroldis Chapman signed a one-year deal for $10.5 million.

In spring training, the Pirates signed veteran free agents Yasmani Grandal and Michael A. Taylor.

Parting Thoughts

To summarize, it’s pretty clear why the Pirates haven’t been able to make a push for the postseason. The offseason acquisitions have not been nearly enough to help launch a team towards contention.

Cherington gets a pass for trying to rebuild the first couple years of his tenure. But now that the Pirates are trying to compete, they should be trying to land impactful free agents who could help the team beyond just one year. Perhaps ownership needs to hear that message.

Maybe the Spencer Horwitz trade will prove to be an important and meaningful addition for the foreseeable future. But even if that’s the case, the Pirates have a lot of work left to do this offseason or we could be looking at a similar story as the first five.