The Pirates finally took a step forward in 2026, but the work that matters most is happening right now.
Pittsburgh finished 82-80, its first winning season since 2018 and only the fifth in the last 34 years. Even with that progress, the season still ended short of October baseball, and the club’s postseason drought now stretches back to 2015, the second-longest in MLB.
That’s why this offseason can’t be treated like a normal one. The current collective bargaining agreement is set to expire on Dec. 1, or at Dec. 2 at midnight, and a new deal is not expected to be in place by then. If that happens, a lockout would follow and transactions would stop, freezing trades and free-agent signings until a new CBA is reached.
For the Pirates, that leaves just 26 days to get moving.
That urgency matters because Pittsburgh has usually been slow to act under general manager Ben Cherington, with most of the club’s offseason business coming in January or February before spring training. The last time around the CBA timeline got in the way, the Pirates signed catcher Roberto Peréz before the old agreement expired in December 2021, then sat tight until the new CBA was finalized in March 2022.
This time, waiting is not an option.
Pittsburgh is projected to carry a $100 million payroll before adding anyone new, which would make it the largest in team history. And there are clear spots that need attention this month: third base, a right-handed power bat who can handle left-handed pitching, and bullpen help.
The biggest priority may be keeping Brandon Lowe. The Pirates extended the top free agent a qualifying offer worth $23.15 million in 2027, but he is expected to look for a longer-term deal. Re-signing Lowe by the end of November should be the club’s main objective, alongside filling out the rest of the roster.
The need to improve against left-handed pitching is obvious. Pittsburgh went 18-33 against starters and posted some of the worst numbers in MLB in that area.
A real third baseman would help, and so would more high-leverage relief arms on both sides of the mound.
The Pirates have a strong lineup, a promising starting rotation and a team that is close to something bigger. But if they miss on these November moves, they risk wasting momentum not just for 2027, but for the broader effort to build a winning culture in Pittsburgh.
Now is the time for the front office and ownership to prove they want to build the best roster possible and reset expectations around this team.
In Other News...
Pirates Trade Fit Could Fix One Lineup Problem And Create Another
The Pirates have spent enough time looking for ways to balance their lineup that a player like Jo Adell is easy to picture on the radar. Hes already being mentioned among the top trade candidates for the 2026-27 offseason, and the appeal is obvious from Pittsburghs side: the club has struggled to do damage against left-handed starters, and a right-handed power bat with Adells profile would fit a clear need.
The catch is that the fit is not clean. Adells overall offensive limitations make him a more complicated bet than the handedness split alone suggests, and the price tag through arbitration only adds to the front offices calculus. For a Pirates team trying to patch one lineup hole without creating another roster headache, this is the kind of decision that can shape the next offseason before it really begins. [Read more 🡒]
Pirates May Have A Tough Call On Spencer Horwitz Soon
Spencer Horwitz arrived as a useful piece for the Pirates, but his first season in Pittsburgh did not unfold the way the club hoped. Injuries slowed him down in 2026, and the dip showed up on both sides of the ball, leaving the Pirates to sort through what he still is for them and where he fits in a roster that already has some overlap at first base.
The front office now has a decision to make with Horwitz and Ryan O'Hearn in the mix, and that could push the Pirates toward a move that creates more flexibility elsewhere. Horwitz still has multiple seasons of team control, which makes the choice more complicated than a simple short-term reset, but the organization may soon have to decide whether the long view or the cleaner roster fit matters more. [Read more 🡒]
Pirates May Have Found An Offseason Fix For Their Lefty Problem
The Pirates spent much of the 2026 season looking for answers against left-handed pitching, and that weakness is likely to shape how they approach the offseason. One name that has surfaced in that conversation is Baltimore third baseman Coby Mayo, a bat-first option who could give Pittsburgh a different kind of look from the right side and help balance a lineup that needs more production in those matchups.
Baltimore is willing to listen on trades, which gives the Pirates a possible path if they decide Mayo is worth the gamble. The appeal is obvious on offense, but Pittsburgh would still have to weigh how steady he can be and whether his glove at third base is good enough to justify the move before anything gets serious. [Read more 🡒]