5 questions looming large over Pirates' offseason

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PITTSBURGH - The Pirates enter the 2026-27 offseason in unfamiliar territory. Pittsburgh is fresh off its first winning season since 2018, completing a 15-9 September to just scrape over the .500 mark at 82-80 and six games out of the final NL Wild Card spot. The next step is making up the ground to break an 11-year postseason drought.

“We've got to stay laser-focused on the work necessary to put ourselves in that position next year that we'll be playing games in October,” general manager Ben Cherington said.

Here are five key questions looming over the Pirates' offseason:

1. Does Brandon Lowe return for an encore?

The addition of Lowe as part of a three-team deal last offseason turned out to be one of the best in baseball. Lowe played a career-high 150 games with 35 home runs and 96 RBIs, while also adding a veteran presence to the Pirates clubhouse and becoming a hero in the community.

Lowe’s contract is up, and he’ll hit the open market as one of the most highly coveted position players available. Cherington described the return of Lowe as a “great outcome if he's a Pirate next year.” But it will cost a pretty penny, likely a sizable increase from the $11.5 million he earned in 2026, and Lowe, at 32 years old, could find interest in a longer-term deal.

• Cherington talks progress, 2027 outlook at end-of-year conference

2. Will a left-handed starter be added to the mix?

Pittsburgh’s starting rotation is both young and talented. With 2025 NL Cy Young winner Paul Skenes at the forefront, Braxton Ashcraft posting a breakout campaign and Jared Jones and Bubba Chandler showing flashes of stardom, there’s plenty to work with. Though how is the fifth spot filled?

Mitch Keller is owed $18.4 million in 2027 and is coming off a season-ending injury, putting his defined spot in doubt. Young arms like Wilber Dotel, Khristian Curtis and Antwone Kelly will add depth, and top prospect (MLB Pipeline’s No. 9 overall) Seth Hernandez is on the way. But adding a left-handed starter could be the perfect combination. An affordable piece like Foster Griffin could be worth the investment after earning his first All-Star nod in 2026.

3. How can you fix woes vs. lefties?

Even amid an offensive breakthrough that saw a franchise single-season home run record, the Pirates couldn’t fix their woes against southpaws. Pittsburgh batted .228 with 3.82 runs per game and an 18-33 record when facing lefty starters.

Having Oneil Cruz and Konnor Griffin healthy will play a part in slightly fixing those numbers, and other returners must improve similar to what Cruz did between 2025-26, moving from a .102 average to .326 against lefties. The Pirates could look to improve externally on the market through players with the ability to play third base, an outfield spot or designated hitter. Third baseman Isaac Paredes is a strong option after recording a .779 OPS against left-handed pitchers. Outfielder Tyrone Taylor is another with a .921 OPS.

4. Where can you supplement Montgomery, Weaver?

A bullpen is only as good as its top arms, and in Mason Montgomery and Luke Weaver, the Pirates have found that. Montgomery has turned into a star closer, and Weaver is a great complement as a right-handed setup man. Pittsburgh’s bullpen finished with a 3.49 ERA and 3.9 fWAR after the Trade Deadline, compared to a 4.34 ERA and 2.3 fWAR beforehand. Where do they go next to take things up to an even higher level?

Yohan Ramírez and Lake Bachar will return and can give bulk. Lefty Brandon Eisert posted a 2.79 ERA in 9 2/3 innings in September, a nice audition for a possible middle-innings spot. Gregory Soto is a free agent after an up-and-down year and Kirby Yates retired. The Pirates would be wise to add at least one arm externally.

5. What staff changes are looming?

Cherington praised the job first-year manager Don Kelly and his staff did to build a winning culture. An 11-win improvement proved that, and there shouldn’t be many changes to the coaching staff – if any – entering 2027.

• Young core has Pirates believing they're ready for next step

The front office will see at least one addition for a domestic director position to run the MLB Draft moving forward. Assistant general manager Kevan Graves ran the 2026 Draft temporarily after the departure of Justin Horowitz, and Cherington hopes to fill that role more permanently going forward. Graves is currently overseeing the process of hiring for the position.