Don Kelly’s résumé already carries some perspective most managers never get. He spent nine seasons in the majors as a player, just finished his first full year running the Pirates, and helped guide Pittsburgh to its first winning season since 2018. Still, for all that experience, there’s one milestone he has never seen in his life: the Pirates winning a postseason series.
That’s the kind of burden that hangs over this job in Pittsburgh. The club did give fans the unforgettable 2013 Wild Card Game, but that was a one-game setup, not a true series victory.
The last time the Pirates won a full postseason series was the 1979 World Series against the Orioles, months before Kelly was born in February 1980. Even Jim Leyland, a Hall of Famer, never managed to snap that streak.
Ben Cherington on Don Kelly: "He’s clearly the right person to manage this team. He’s someone I love coming to work with every day. Our goals are the same: Do the work necessary to play games in October."
The scale of Pittsburgh’s drought looks even harsher when stacked against the rest of the league. Only the Mariners have gone longer without reaching a championship round, and Seattle’s trip to the ALCS in 2025 means the Pirates now hold the longest gap between LCS appearances.
Of course, the first hurdle is simply getting back to the postseason. Pittsburgh finished 82-80 in a strong National League and landed six games out of the Wild Card race. That same record would have been good enough to win the AL West, which only adds fuel to the ongoing debate about the imbalance between leagues and the playoff structure that’s sure to be part of the next CBA discussion.
As for how Kelly gets out from under all that history, the early offseason chatter doesn’t suggest much immediate help from the front office. Cherington already appears ready to move on from Brandon Lowe, the team’s most valuable and consistent offensive player.
So if this is going to change, Kelly may have to do a lot of the heavy lifting himself. Maybe a little hometown magic can help, too.
In Other News...
Astros Trade Looks Different After What Pittsburgh Got Out Of It
The three-team deal with the Astros and Rays has taken on a much different look for Pittsburgh after the Pirates pulled real value out of it on both sides of the ball. Brandon Lowe gave the lineup a steady boost and held up defensively, Mason Montgomery developed into a late-season bullpen weapon, and Jake Mangum filled in as a dependable fourth outfielder when injuries opened the door.
For a club trying to build on an improved stretch, that kind of return matters because it goes beyond one quick fix. Lowe looks like a player who can matter again next season, Montgomerys emergence gives the relief corps another late-inning option, and Mangums role showed how useful depth can be over a long year, even if the bigger question still hangs over how the Pirates will sort out all three moving forward. [Read more 🡒]
Pirates Face Two Tough Replacements In A Risky Offseason Reset
The Pirates offseason already has a familiar feel to it, with two important spots sitting on the board before the winter really gets moving. Brandon Lowes left-handed bat gave them a steady presence at second base, while Gregory Soto added a power arm from the left side out of the bullpen, and both are now free agents after solid seasons in Pittsburgh. That leaves the front office balancing short-term stability against the reality that both jobs may have to be filled from a market that is never especially generous.
Finding replacements at second base and in the relief corps is never simple, but the Pirates have a few ways to attack it. They can look inward for internal options, browse the free-agent market for fits, or explore trade possibilities if they want to reshape the roster more aggressively. However they approach it, the challenge is the same: replacing two useful players without weakening a team that cant afford many missed bets. [Read more 🡒]
Pirates Prospect Wyatt Sanford Is Forcing A Bigger Future Conversation
Wyatt Sanfords Arizona Fall League start gave the Pirates another reminder that his rise is no longer just about smooth defense at shortstop. The prospect opened the 2026 AFL season by hitting the first home run of the league for the Glendale Desert Dogs, a fitting snapshot for a player whose offensive profile has started to move forward in a meaningful way.
Sanfords power gains have been building throughout the 2026 season, and the swing tweaks he made helped drive both better exit velocity and more home run production. With a Double-A Altoona assignment expected to begin next year, the conversation around him is shifting from upside to timing, and Pittsburgh now has a prospect whose bat is making it harder to keep his future in the background. [Read more 🡒]