The Pittsburgh Pirates wanted to be in the playoffs in 2026, but are on the outside looking in once again.
On September 29, 2025, Pittsburgh Pirates president Travis Williams said the team's goal for the 2026 season was to make the playoffs: “Period. Full stop.”
In the months that followed, the organization acted like one that wanted to be playing October baseball.
The Pirates made their blockbuster trade of the winter, acquiring Brandon Lowe, and also signed two free-agent veterans, Ryan O’Hearn and Marcell Ozuna. One of those obviously worked out much better than the other.
Even after all of those moves, Pittsburgh stayed aggressive throughout the season, too.
Top prospect Konnor Griffin was called up just a few weeks after Opening Day, and Pittsburgh was ultra-active in finding high-leverage bullpen arms leading up to the trade deadline. They acquired Luke Weaver, Camilo Doval, and Kirby Yates ahead of the August 3 deadline.
However, as the Wild Card rounds continue this week and the top two seeds in the National League get byes and await the winners to start the NLDS, Pittsburgh is in the same spot it's been for the last 12 seasons: on the outside looking in.
The Pirates fell short of the goal they set, and general manager Ben Cherington admitted as much during the final weekend of the regular season. The GM explained that the team’s focus hasn’t changed, though.
Pittsburgh wants to remain competitive, but even Cherington acknowledges that there is a lot of work to do.
Sep 1, 2026; Pittsburgh, Pennsylvania, USA; Pittsburgh Pirates catcher Rafael Flores Jr. (left) is congratulated by Pittsburgh Pirates second baseman Brandon Lowe (5) and third baseman Nick Yorke (38) and shortstop Jared Triolo (19) after Flores drove in the game winning run on a San Francisco Giants error at PNC Park. Mandatory Credit: Charles LeClaire-Imagn ImagesDespite the Pirates failing to reach the playoffs, Cherington stressed that Pittsburgh's progress and development from the core throughout the season are worth noting and encouraging.
Ignoring the disappointment of the Pirates not being a playoff team for a minute, the general manager is correct.
Pittsburgh went from having the worst OPS in baseball following the 2025 season (.655), to having the sixth-best (.734). This alone helped the Pirates increase their win total by 10 games from a year ago and reach their most wins since 2018.
The pitching definitely had its highs and lows, but it still found its close of the season, as Mason Montgomery was one of the top relievers in all of baseball during the final month of the season.
With all that said, the question still remains: How do the Pirates get back to the playoffs? The organization seemingly did everything right over the last few months to build a short-term winner, but still missed out on the postseason.
If the Pirates are truly set on being a postseason team in 2027, it might be time for the front office to get even more uncomfortable with some of their offseason moves to build a winner.
