3 positions the Pirates absolutely cannot leave unresolved this winter

The Pittsburgh Pirates have spent far too many offseasons convincing themselves that uncertainty can double as depth.

Sometimes it's framed as competition. Sometimes it's framed as flexibility. More often than not, it becomes a roster hole everyone could see coming months before Opening Day. But that can't happen again this winter.

For all the decisions facing the Pirates after the 2026 season, three positions should sit near the very top of Ben Cherington’s offseason checklist. They don't necessarily need a star at all three, but they do need actual answers.

3 positions the Pirates cannot leave unresolved during 2026-27 offseason

Catcher

Henry Davis’ recent offensive flashes are encouraging, but they certainly aren't enough to hand him the starting catching job for 2027 without a contingency plan.

Davis' power remains intriguing, and he has made legitimate strides defensively behind the plate. But the offensive production has still been far below what Pittsburgh needs from an everyday player — especially one drafted first overall in 2021.

The larger complication is Endy Rodríguez, who underwent surgery in August to repair the labrum in his left hip and was given a seven-to-nine-month recovery timeline. Even under an optimistic schedule, that puts his availability for the beginning of next season in question. The Pirates can't simply assume Rodríguez returns on schedule, immediately handles a major workload and looks like the same player who was producing before the injury.

The emergence of Rafael Flores Jr. has been one of the more encouraging offensive developments in the organization this season. He has forced his way into the conversation as a potentially meaningful part of Pittsburgh’s future behind the plate, giving the Pirates another young option beyond Davis and Rodríguez.

But Flores is still developing, and the Pirates can't allow another promising young player to become their justification for standing pat. There is a difference between having legitimate upside at a position and knowing exactly what the major league plan is.

If Pittsburgh believes Davis is its catcher, fine. Then acquire a legitimate veteran backup capable of playing regularly if necessary while Flores continues developing and Rodríguez works his way back. If the organization still has doubts about Davis, catcher needs to become a much more aggressive offseason target.

Flores’ breakout should make the Pirates more comfortable with their long-term catching depth, but it shouldn't make them complacent about 2027. There has to be a plan beyond hoping one of Davis, Rodríguez or Flores becomes the answer on schedule.

Second base

Brandon Lowe has provided exactly the kind of legitimate offensive production from second base that the Pirates have lacked for years. That has also exposed how dangerous it would be to go backward.

Lowe has given Pittsburgh middle-of-the-order power and is making a legitimate Silver Slugger case. Whether he remains part of the long-term picture will depend on the Pirates’ contractual decisions and how aggressively ownership is willing to spend, but replacing his production internally would be difficult.

Nick Gonzales can play second. So can several other players in the organization. But that doesn't mean Pittsburgh should be comfortable simply handing the position to whichever internal option is left standing.

The Pirates finally have the foundation of a lineup that can be dangerous when healthy. Konnor Griffin should be a fixture, Oneil Cruz provides enormous upside, and Ryan O’Hearn has been one of their better hitters when available. Removing a proven bat from that group and replacing it with another question mark would be classic Pirates roster construction: solve one problem, then voluntarily recreate it.

If Lowe isn't back — and he likely won't be — Pittsburgh needs to replace the offense, not merely fill the position.

Third base

Third base might be the most obvious example of a position the Pirates cannot allow to drift into spring training unresolved, especially after they've spent much of this season searching for someone to claim it.

Jared Triolo remains the defensive baseline. Nick Gonzales has enough offensive ability to enter the conversation, but his defense has made him a difficult long-term fit there. Jacob Gonzalez is getting an opportunity, but Pittsburgh still needs to determine whether he can hit enough to become more than a glove-first option. None of that qualifies as certainty.

The Ke’Bryan Hayes era ended because the Pirates decided elite defense alone wasn't enough if the bat couldn't justify everyday playing time. It would make no sense to immediately recreate the same problem with another player.

Pittsburgh simply needs someone capable of providing league-average offense while making routine plays defensively at third base. That shouldn't be an unreasonable standard for a team claiming it intends to contend.

That's ultimately what ties all three positions together. The Pirates are past the point where every offseason can be treated like another development year. They have the foundation of a competitive roster, and that creates urgency.

Catcher can't be Davis-or-bust — nor can Flores’ emergence become another reason to wait. Second base can't become a dramatic offensive downgrade. Third base can't be another six-month experiment.

The Pirates need certainty this winter. After years of entering seasons with obvious holes and hoping someone unexpectedly fills them, that would represent progress all by itself.

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