3 Biggest Questions Facing Pirates Entering Critical Offseason

The Pittsburgh Pirates are entering a critical offseason, following a much more competitive season in 2026.

Pittsburgh ended the year with a record of 82-80, and while they didn't make the playoffs, it was still a successful season. The future is very bright for the Pirates, and this coming winter could shape everything for the organization.

Here are three of the biggest questions surrounding the Pirates as they enter the offseason:

1. Will Pirates Retain Brandon Lowe?

Lowe will be entering free agency this winter after putting together a very strong year for the Pirates. Many around the league are wondering whether the Pirates will keep Lowe around, especially considering the track record of the front office.

But the veteran was a central piece of the Pittsburgh offense this season, and keeping him in town may be necessary. Lowe is 32 years old, and teams may be wary of how he will continue to age, but for the Pirates, bringing him back makes sense.

Overall, Lowe hit .260 with 35 home runs and 95 RBIs, while posting an OPS of .824. Lowe will have multiple suitors, but the Pirates may want to be aggressive with him.

2. Can Pirates Fix Left-Handed Hitting Issues?

The Pirates were one of the worst hitting teams in the league against left-handed pitchers, and this is a problem. Pittsburgh has to find a way to deal with this, whether that is bringing in guys who mash lefties, or improving internally.

The team saw a .701 OPS against left-handers this year, which was good for 19th overall in baseball. For a team with playoff aspirations, this just isn't going to get the job done.

Pittsburgh has some work to do this year, and the hope is that fixing this problem can get them back into the postseason. But how the front office plans to address this remains unknown at this time.

3. Can Paul Skenes Bounce Back?

One of the stranger parts of the 2026 season was the down year that ace Paul Skenes put together. After two years posting sub-2.00 ERAs, Skenes struggled this year, finishing the season with a 3.82 ERA over 32 starts.

Skenes blamed him pitching in the World Baseball Classic as a reason for the issues, but his decline held the Pirates back. But if he can get back to being the top pitcher that Pittsburgh knows he can be, the sky is the limit for this team.

Given where the Pirates are, Skenes is as important to the success of this team as anyone in the league. Skenes will look to bounce back next year, giving this team another boost at the top of the rotation.