The Pirates are watching October from the outside while the kind of teams they want to become are still alive.
Tampa Bay rolled through the New York Yankees in the American League Division Series and now moves on to the AL Championship Series, where the Rays will face either the Chicago White Sox or the Cleveland Guardians. That path guarantees one of the lowest-payroll clubs in baseball will end up in the World Series.
Milwaukee is in the same position on the National League side. The Brewers beat the San Diego Padres in four games and advanced to the NL Championship Series, where they will meet the Los Angeles Dodgers, a team with the second-highest payroll in baseball at $339 million and the self-described “villains” of the sport as they chase a third straight World Series title.
For Pittsburgh, the sight is especially bitter. The Pirates’ National League Central rival is moving forward, and the franchise that still hasn’t come close to the World Series in nearly five decades is left measuring itself against clubs that have found a way to win without spending at the top of the market.
Under owner Bob Nutting, who became the majority owner in 2007, Pittsburgh has consistently operated with one of the smallest payrolls in baseball. This year, though, the Pirates did push past $100 million for the first time since 2016, finishing at almost $107 million according to Spotrac. That ranked 23rd overall, or eighth-lowest in the majors.
Even with that modest bump, the Pirates’ payroll still topped every American League team remaining in the postseason. The White Sox were at $103 million, the Rays at $96 million and the Guardians at $74 million. Milwaukee finished ahead of Pittsburgh at $146 million, but that still placed the Brewers 19th in baseball, hardly an elite-spending club.
The bigger problem for the Pirates has never been just payroll. It’s the long stretch of losing that has defined the franchise.
Pittsburgh endured 20 straight losing seasons from 1993 to 2012, a North American professional sports record. Over the past 34 seasons, the Pirates have managed just five winning seasons, including 82-80 in 2026, and only three postseason trips, all from 2013-15.
That makes the current postseason especially jarring, because the teams still standing have built something far sturdier. Tampa Bay, an expansion team that began play in 1998, has reached the playoffs 10 times since 2008, won five AL East titles and captured pennants in 2008 and 2020. Milwaukee has also been in October 10 times since 2008, winning the NL Central seven times, including five times this decade and each of the past three seasons.
The White Sox have their own recent success to point to, with four AL Central titles and two Wild Card berths this century, even if the franchise has been through a brutal rebuild. Chicago went from 41-121 in 2024, the most losses ever by an AL team, to 60-102 in 2025 and then 84-78 with a Wild Card berth in 2026. Cleveland, meanwhile, has reached the postseason 16 times, won the AL Central 14 times and made the playoffs in 1995, 1997 and 2016 over the same 34-year span in which Pittsburgh has been mostly chasing.
There is at least some reason for optimism in Pittsburgh’s own season. The Pirates spent much of the year in the NL Wild Card race, recovered from a rough 7-16 stretch from late July into mid-August and still finished with a winning record. They also believe the pieces are starting to come together, with a strong and young starting rotation, a formidable lineup and a bullpen that could become a strength with a few additions.
They will need to keep building carefully for next season. If the roster comes together and the stars stay healthy compared to 2026, the Pirates could have a real shot at being in the October conversation in 2027.
In Other News...
Pirates Face A Tough Decision On A Power Bat They Need
The Pirates have spent enough time looking for right-handed thump that any bat with real power immediately draws attention, and Jo Adells recent playoff showing has only sharpened that interest. Clevelands outfielder has the kind of pop that can change a lineups shape, especially against left-handed pitching, which is exactly the area Pittsburgh needs help if it is going to balance out a roster that has too often come up short in those spots.
For the Pirates, the appeal is obvious, but so is the decision ahead of them. They need offense, they need it from the right side, and they need a player who can fit into a lineup that still has holes to fill. Adell checks enough of those boxes to make him a name worth tracking this offseason, even if nothing about his future has been settled yet. [Read more 🡒]
Pirates Face One Offseason Problem They Cant Keep Ignoring
Third base has moved to the front of the Pirates offseason to-do list, and it is easy to see why. After moving on from KeBryan Hayes, Pittsburgh tried to cover the spot with Nick Gonzales, who offered a better bat but did not solve the defensive side of the equation. The front office now views the position as one of the key areas that needs a real upgrade for the 2027 season, not just a temporary patch.
There are internal names in the mix, including prospects still working their way up the ladder, but the Pirates are expected to keep looking outside the organization for more power and steadier defense. They have explored both free agency and trade possibilities for a third baseman who can lengthen the lineup and handle the job cleanly, even as some of the targets they monitored have already gone elsewhere. The search is still open, and for a club trying to build around young talent, getting this one right matters. [Read more 🡒]
Paul Skenes Just Faced His First Real Pirates Test
Paul Skenes entered his first two major league seasons looking every bit like the franchise arm the Pirates had envisioned, collecting National League Rookie of the Year honors and then following it with an NL Cy Young Award. But 2026 brought a different kind of test, as his run prevention slipped and his fastball no longer carried quite the same edge, forcing him to work through a stretch that asked more of his craft than his overpowering stuff.
For a pitcher whose early success was built on dominance, the challenge was never just about surviving a down year, but about proving he could adjust when hitters and his own body gave him less margin for error. By seasons end, there were signs of progress in that effort, including a second straight 200-strikeout season, a reminder that even amid the dip, Skenes was still finding ways to miss bats while he searched for the next version of himself. [Read more 🡒]