Baseball's offseason is underway, and it is a critical one for Pittsburgh Pirates general manager Ben Cherington.
Pirates owner Bob Nutting said at the end of this past season that there is "urgency" to win now. However, the Pirates went 71-91 this year and finished last in the National League Central, regressing following back-to-back 76-86 seasons.
It will be interesting to see if Nutting puts his money where his mouth is. Cherington has been strapped with extremely small payrolls since being hired before the 2020 season, and the Pirates have not had a winning season during his six years on the job.
Furthermore, the Pirates have not signed any free agents to a multi-year contract since 2016. Thus, Cherington has to find players poised for bounce-back years or veterans whom the Pirates might be able to squeeze out one last decent season.
The most prominent bright spot for the Pirates last season was their pitching staff, which finished seventh in ERA among Major League Baseball teams. NL Cy Young favorite Paul Skenes leads a talented rotation that includes Mitch Keller, Johan Oviedo, and three pitchers who were rookies in 2025 --- Bubba Chandler, Braxton Ashcraft, and Mike Burrows.
However, that rotation needs offensive support. The Pirates finished last in MLB in runs scored, home runs, and OPS. As good as the pitching is, it's unfair to continue expecting it to win games 1-0 or 2-1 or 3-2.
The most significant holes in the lineup are at third base, shortstop, and left field following the trade of Hayes, the release of Isiah Kiner-Falefa, and Tommy Pham becoming a free agent.
Dennis Santana did an admirable job as the closer following the trade of two-time All-Star David Bednar to the New York Yankees at the deadline. The Pirates, though, could use some reinforcements in the bullpen, especially a left-hander or two.
Cherington should have around $30 million to spend on free agents with the savings the Pirates netted by dealing third baseman Ke'Bryan Hayes to the Cincinnati Reds at the deadline. Another option the Pirates could use to acquire is trading Keller, who should draw interest from pitching-needy teams.
Keller was an All-Star in 2023, but his most valuable asset is his availability, as he has averaged 177 innings pitched over the past four seasons. The Pirates may not get the impact hitter they desire in a trade for Keller. However, trading Keller would free up more money for potential free agent signings, as he has approximately $55 million remaining on the final three years of his five-year, $ 77-million contract.
Other than Pham, the only player who entered free agency is designated hitter Andrew McCutchen. He is a franchise icon, but also 39, and said late in the season that he wants to play for a winning team. The gut feeling is that the Pirates and McCutchen will part ways.
Santana and Oviedo are among a group of nine players eligible for salary arbitration, along with relievers Colin Holderman, Justin Lawrence, Dauri Moreta, and Yohan Ramirez, catcher Joey Bart, center fielder Oneil Cruz, and outfielder Jack Suwinski.
It is unlikely that the Pirates will tender contracts to all nine players. The roster spots of Holderman, Moreta, Ramirez, and Suwinski could be particularly vulnerable.