The Pittsburgh Pirates have a big winter coming, and the lesson from their recent past is pretty clear: when they’ve played it safe in free agency, it has cost them.
Pittsburgh is coming off an 82-80 season in 2026, its fifth winning year in the last 34, but the club still finished well short of the postseason for the 10th season away from October. The roster gives them something to build on - a young, dominant rotation, a bullpen that settled in after the trade deadline and a lineup with enough pop to drive in runs - but that kind of core only matters if the front office adds to it.
The Pirates have already lived through the danger of standing still. After going 76-86 in 2024, they were still above .500 and in the National League Wild Card race at the trade deadline.
Then August went sideways, with an 8-19 skid that sank the season. Even so, there was still a real sense they could carry that group forward, especially after Paul Skenes and Jared Jones made their debuts.
Instead, the offseason that followed was a letdown. Pittsburgh’s moves were limited to Tommy Pham, Adam Frazier, Andrew Heaney and Caleb Ferguson in free agency, plus a trade for Spencer Horwitz. Horwitz needed wrist surgery and didn’t debut until mid-May, which only added to the sense that the Pirates hadn’t done enough to push the roster forward.
That lack of urgency showed up fast. The 2025 season turned into a mess on the field and off it, ending with a 12-26 start and the firing of Derek Shelton after more than five seasons as manager.
Don Kelly took over, but the results never changed much. Pittsburgh finished 71-91, dropped to its seventh straight losing season and again missed a chance to build on a season that had still left some room for hope.
They also wasted a year in which Skenes won the National League Cy Young Award.
The following offseason was a better response. The Pirates traded for Brandon Lowe, Jake Mangum and Mason Montgomery from the Tampa Bay Rays, then signed Ryan O’Hearn to a two-year, $29 million deal. That contract mattered on a few levels: it was the first multi-year free agent signing since 2016, and it carried the largest AAV per free agent contract in franchise history.
Those moves paid off. Lowe delivered the best power of any second baseman, Mangum covered the outfield, and Montgomery turned into a dominant closer. O’Hearn was excellent in the first half and looked like he had been snubbed from the All-Star Game before a quad injury derailed the back half of his season.
But Pittsburgh also spent $12 million on Marcell Ozuna, and that was the swing that missed. Ozuna hit .203/.286/.327 with an OPS of .613 in 70 games, belted just eight home runs and was designated for assignment in early August. That money could have gone elsewhere, and the Pirates had obvious places to spend it: a right-handed power bat, a third baseman or another shutdown reliever.
That’s where the warning sign really lives. The bullpen got only Gregory Soto, and the Pirates never fixed their issues against left-handed starting pitching, where they went 18-33. Better additions in those spots could have meant more wins and a tighter postseason push.
Now the Pirates are staring at another pivotal winter with a possible lockout looming, since the current collective bargaining agreement expires on Dec. 1. Before baseball potentially shuts down, Pittsburgh and the rest of the league will try to get business done.
For the Pirates, the biggest move may be the simplest one: keep Lowe. Re-signing him would send a strong message to the clubhouse and the fan base that this front office is serious about the playoffs in 2027 and beyond. From there, more help in the bullpen and at third base would make sense.
Pittsburgh can’t afford another winter of half-measures.
In Other News...
Pirates Have An Old Friend Who Could Fix A Big Bullpen Need
The Pirates spent a lot of the offseason looking at ways to shore up a bullpen that could use more stability, and one familiar name keeps making sense. David Bednar, now with the Yankees, has put together a strong run in New York while reminding everyone what Pittsburgh already knew during his previous stint here: when he is right, he can be a late-inning arm a club can lean on. For a team trying to map out its relief mix, that kind of track record matters.
Bringing Bednar back would also fit the Pirates broader search for more dependable options around the relief corps, where one addition can change how the whole group is deployed. There is still plenty to sort through on the roster front, but an old friend with recent success elsewhere gives Pittsburgh a straightforward path to addressing a clear need. Whether the fit becomes real is the part still waiting to be answered. [Read more 🡒]
Pirates Face A Costly Rotation Decision Fans Can't Ignore
The Pirates offseason could turn quickly from evaluation to hard choices, and Mitch Keller sits at the center of it. The right-hander is coming off a rough stretch after an injury, and with a five-year extension already on the books, his deal now carries heavier salary obligations in the later years. For a club that has spent the past season leaning on a promising young rotation, the question is no longer whether Keller has value, but whether that value still fits the rest of the roster.
Pittsburgh has reason to believe it can cover innings in other ways, whether by turning to cheaper arms or giving another rookie a larger role. That kind of depth makes Keller easier to discuss in trade terms, even if moving him would mean giving up a pitcher who was supposed to be part of the long-term core. The challenge for the Pirates is balancing present performance with future payroll, and Kellers contract makes that decision even harder to avoid. [Read more 🡒]
Pirates Could Be Facing An Uncomfortable Oscar Marin What-If
Oscar Marins next stop could put the Pirates in an awkward spot. The former Pittsburgh pitching coach is now in the mix to become the Cincinnati Reds next pitching coach after Derek Johnsons departure, a development that brings his name back into the division conversation not long after the Pirates chose not to retain him following the 2025 season.
Marins case in Cincinnati has only grown stronger since he took over as the Reds bullpen coach and helped manage the staff during Johnsons personal leave. For the Pirates, it is the kind of what-if that lingers because their pitching groups performed well under his watch, and a promotion elsewhere would only sharpen the question of why that run in Pittsburgh ended when it did. [Read more 🡒]