AP Photo/Keith Sarkocic

Ben Cherington has been the general manager for one year of rebuilding, albeit not a normal season at all. The Pirates will look to continue to rebuild after finishing 19-41 in the shortened 2020 season. The circumstances of this past season occasionally made it difficult for Pittsburgh’s general manager to act on that vision in his first year at the helm, but the Pirates could be busier this winter.

“How do we build a stronger, more talented roster that gives us a chance to get into a more sustainable period of winning? Usually, that’s through acquisition and development of younger players, talented players, and then bringing them into their primes in the Major Leagues,” Cherington said. “Most often, in free agency, that’s not the kind of player that’s available. Free agency is used as part of a team-building process, for sure, and it’s an important part of the team-building process, but it depends on where you are in your build.

“I think there will be opportunities for us in free agency this offseason. I don’t know what they will be yet. I just think that we need more time. But we need to be focused on building a deeper, more talented roster, and most of that’s going to come through retaining and continuing to add young talent that can develop and grow together.”

Premium Prospects

In order to build a long term contender in the National League. the Pirates will need to rebuild their base of talent. Some of their young players should help form the core of that team, but they lack star-level production and quality depth at the highest level. They will also add the number one pick for 2021 to their young roster.

The Pirates will likely consider trading away some established players to target younger, high ceiling prospects, similar to the Starling Marte trade last year. This trade netted them two exciting prospects and additional internationals spending capacity.

“It’s fair to say some of the avenues we thought we were going to be able to go down during the 2020 season were impacted, either by the pandemic or by injury or by other things,” Cherington said. “We’ve added talent to the organization in the last year through different avenues, but it also means we’ve just got to continue to be really focused on building a stronger base of talent and finding an opportunity to do that, whether it’s through amateur means or whether it’s in trades and including free agency.”


Bryan Reynolds will start in the outfield, but the Pirates are unsure if he will be in left or center or as part of a rotation. They could keep using shortstop Cole Tucker in the outfield as they did in 2020. But why not scour the free-agent market for a veteran outfielder who could play a role and possibly intrigue a contender before the Trade Deadline?


The Pirates have a lot of options in the bullpen, but very few are sure things. There are a ton of quality pitcher available this offseason, so look for the Pirates to pursue one or two of them or potentially flip some of the back end arms.

Catching Depth – Potentially Addressed

The Pirates claimed former Rays backup Michael Perez already this offseason, to be the backup to Jacob Stallings. But those two are the only catchers on the Pirates’ 40-man roster, so expect the Bucs to be active in acquiring additional help behind the plate. That could lead them to a more proven backup for Stallings, or maybe they’ll lean toward the model of defense-first veterans on Minor League deals.

One of the most important things the Pirates need to do at some point is acquire their catcher of the future. There are no catchers among their Top 30 Prospects, according to MLB Pipeline.

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