The Pirates are heading into an important winter with something they haven’t had in a while: room to dream a little bigger.
Pittsburgh is coming off an 82-80 season, its first winning year since 2018, and the core they brought back from 2026 gives the club a real chance to turn 2027 into something special. But if the Pirates want to push deeper into the playoff picture, that next step is going to require real money.
That’s the catch with this roster. The Pirates are still a small-market team with a reputation for keeping payroll tight, but they may be willing to spend more than usual as they chase a postseason return for the first time since 2015, the second-longest drought in Major League Baseball.
At the moment, Pittsburgh already has five players locked in for 2027 and not tied to arbitration or pre-arbitration.
Mitch Keller is set to be the club’s top-paid player at $18 million, the fourth season of the five-year, $77 million extension he signed before the 2024 season. Ryan O’Hearn and Bryan Reynolds are both due $15 million. O’Hearn is in the final year of his two-year, $29 million deal, while Reynolds is in the fifth season of the $106.75 million extension he signed in 2023.
Luke Weaver is also on the books, though the Pirates are only responsible for part of that salary. The right-handed reliever will make $11 million in the second year of his two-year, $22 million deal with the New York Mets, but the Mets are paying $6 million of his 2027 salary, leaving Pittsburgh on the hook for $5 million after acquiring him for shortstop prospect Sammy Stafura.
Shortstop Konnor Griffin is also under contract, set to earn $2 million in the second year of the nine-year, $140 million extension he signed with Pittsburgh on Oct. 8.
The bigger chunk of the roster sits in arbitration. The Pirates have 10 players headed there in 2027, including eight in their first year of eligibility. Oneil Cruz and Yohan Ramírez are the two players moving into their second year of arbitration after strong seasons.
The first-timers include right-handers Jared Jones, Carmen Mlodzinski and Paul Skenes; infielders Nick Gonzales, Spencer Horwitz and Jared Triolo; and catchers Henry Davis and Endy Rodríguez. Skenes and Cruz are projected to be the biggest earners in that group at $7.2 million and $6.3 million.
Then there’s the rest of the roster picture, with 25 other players on the 40-man roster set to sign for 2027. That group includes pre-arbitration players who typically make close to the league minimum, which was $780,000 in 2026, though no figure has been set for 2027 because there is no collective bargaining agreement in place.
Among the notable pre-arbitration names are Braxton Ashcraft, Bubba Chandler, Mason Montgomery, Jake Mangum, Esmerlyn Valdez and catcher Rafael Flores Jr.
All of that adds up to a projected payroll of $100 million before Pittsburgh even makes a trade or signs a free agent. That’s already near where the Pirates opened this past season, when they were close to $100 million on Opening Day and finished around $107 million, one of the highest payrolls in Bob Nutting’s ownership era.
There are still clear roster holes to fill, but that projected number suggests the Pirates probably won’t wander too far above it. A range of $110 million to $120 million looks like the most realistic ceiling, which would naturally tighten their room in free agency, including any push to bring back second baseman Brandon Lowe.
A trade could help create more flexibility, and Keller is one possible name if Pittsburgh chooses that route. Even then, the Pirates would still be paying part of his $18 million salary.
So the offseason arrives with a familiar kind of pressure for Pittsburgh: the need to find the right balance between spending enough to support a contender and staying within the limits that have defined the franchise for years.
In Other News...
Bob Nutting Could Finally Face Pressure To Spend More
The latest labor talks around Major League Baseball have added a fresh wrinkle for teams that already live near the bottom of the spending ladder, and Pittsburgh is squarely in that conversation. Owners have floated a sweeping economic overhaul for the next collective bargaining agreement, including a salary cap and a payroll floor, as negotiations inch toward what could become a serious work stoppage with the MLB Players Association pushing back hard.
For Bob Nutting, the proposal could create a rare kind of pressure to spend, since the Pirates have long operated far below the levels being discussed. A new framework would force clubs like Pittsburgh to rethink how they build, and even by the standards of a sport used to financial haves and have-nots, it would represent a major shift in the expectations placed on ownership. [Read more 🡒]
Former Pirates Are Still Chasing October While Pittsburgh Watches Again
Pittsburgh is once again watching the postseason from home, but a handful of familiar names are still in the October mix elsewhere. Tyler Glasnow remains the most prominent former Pirate still standing, now part of the Dodgers playoff push after his route out of Pittsburgh began in the Chris Archer trade. Around him, a small group of ex-Pirates has surfaced on other contenders too, keeping a little bit of old black-and-gold bloodline alive deep into the fall.
Ryan Vilade is with the Rays, Austin Hedges is in the Guardians orbit, and Colin Holderman had been in position to be part of the same conversation before a season-ending wrist surgery took him out of the picture. The list is a reminder of how often Pittsburghs recent roster churn has left the club tracking familiar faces in October while trying to build a version of that same relevance for itself. [Read more 🡒]
Pirates Suddenly Face A Tough David Bednar Decision
The Pirates have a bullpen question looming that could shape their late-inning plans for years. David Bednar has rebuilt his value as a closer with the Yankees, and his performance has him positioned to be one of the more sought-after relief arms on the market when he reaches free agency after the 2026 season. For Pittsburgh, the appeal is obvious, especially for a franchise that has spent plenty of time searching for reliable ninth-inning answers.
But the calculus is not simple, because Mason Montgomery has given the Pirates a real internal option. He has emerged as one of the club's most dependable bullpen pieces, and his closing ability has already made him more than just a fill-in solution. The question now is whether Pittsburgh wants to chase a costly external fix when it may already have a reliever under control who has earned a bigger role. [Read more 🡒]