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The Pittsburgh Pirates have not appeared in a postseason game in a full decade. Their last October experience came to an abrupt end on a cool night at PNC Park against the Chicago Cubs when soon-to-be-named 2015 NL Cy Young Award winner Jake Arrieta walked the walk, tossing a complete game shutout in a 1-0 Cubs victory.
Coming off a 71-91 record in 2025, Pittsburgh has its work cut out for it if it wants to snap that streak next season. Despite having Paul Skenes atop the rotation, the Pirates have finished in last place in the division in each of the last two years - but they're hoping to start trending in the right direction sooner rather than later.
The Marlins and Pirates are telling agents they'd like to be aggressive and spend a little bit, says @Ken_Rosenthal.
— Foul Territory (@FoulTerritoryTV) November 11, 2025
"That can be in free agency, or it can be in the matter of taking on salaries in trades." pic.twitter.com/R5aAqrIVa2
Pirates getting aggressive? Here's how it could impact the Cubs
According to Ken Rosenthal, the Pirates and Miami Marlins - two teams that have historically ranked near the bottom of the league in payroll - could be more aggressive this winter. That aggressiveness could come in the form of free agency or through taking on salary via trade.
That report comes hot on the heels of a rumor that Skenes wants to pitch for the New York Yankees - so showing any ability to put a more competitive roster around him in 2026 has to be a top priority for the Pirates and GM Ben Cherington.
Now, nobody expects the Pirates to go from worst to first next year. Between the Cubs and Brewers, there are two clear-cut contenders in the division - and even a team like the Reds is a lot closer to the top than the Bucs. But legitimate steps to improve around Skenes could end up having a big impact in the NL Central and how things shake out in the standings.
Chicago and Milwaukee both went 10-3 against the Pirates in 2025. A more competitive Pirates team, rather than the punching bag they resembled this summer, could help narrow the gap between the Cubs and Brewers and teams like the Reds and Cardinals - and put the pressure on Jed Hoyer to leave no stone unturned as he looks to remake his pitching staff in the months to come.