The Pirates are home for October again, but a few familiar faces are still chasing a ring elsewhere.
Pittsburgh’s postseason drought reached an 11th straight year, yet former Pirates are scattered across the Championship Series field. Some names that once mattered in Pittsburgh already disappeared in the Division Series - Gerrit Cole and David Bednar with the New York Yankees, plus Joe Musgrove with the San Diego Padres - but there are still ex-Bucs alive with the Los Angeles Dodgers, Tampa Bay Rays and Cleveland Guardians.
One club with no Pirates ties left in the mix is Milwaukee. The Brewers’ 26-man NLCS roster does not include a former Pirate, even though Quinn Priester would have been a strong candidate if he had stayed healthy.
Priester, who was traded to the Boston Red Sox at the 2024 trade deadline for Nick Yorke before later being rerouted to Milwaukee, put together a 3.32 ERA in 157 1/3 innings for the club in 2025. His season ended in June after thoracic outlet decompression surgery.
The Dodgers’ connection is headlined by Tyler Glasnow, and there’s no mistaking why. The right-hander was Pittsburgh’s fifth-round pick in 2011 and climbed all the way to No. 9 on MLB Pipeline’s rankings ahead of the 2017 season. That promise never fully turned into production in Pittsburgh, where he logged a 5.79 ERA in 56 appearances, including 17 starts, from 2016 to 2018 before being shipped to Tampa Bay with Austin Meadows and Shane Baz in the 2018 deadline deal for Chris Archer.
Glasnow eventually became an ace with the Rays, even while injuries kept interrupting his run. He finished with a 3.20 ERA and 526 strikeouts in 71 starts covering 388 1/3 innings for Tampa Bay.
Ahead of the 2024 season, he was traded to his hometown Dodgers and later landed a five-year extension worth $136.5 million. In Los Angeles, he has posted a 3.41 ERA in 53 regular season starts and a 1.73 ERA across seven playoff appearances, four of them starts.
The 33-year-old is now trying to help the Dodgers win their third straight World Series after giving up one earned run in 4 2/3 innings in the decisive Game 4 of the NLDS against the Atlanta Braves.
Tampa Bay’s only former Pirate on its ALCS roster is Ryan Vilade, though he never actually played a big league game for Pittsburgh. The Rockies took him in the second round in 2017, and the Pirates claimed him off waivers in November 2022.
He was designated for assignment in March 2023, cleared waivers, and went outright to Triple-A Indianapolis, where he hit .270/.370/.382 with six homers and 56 RBIs. Vilade left the organization after that season and has since hit .245/.321/.429 with 11 home runs and 43 RBIs in 278 plate appearances for the Rays this year.
He also went deep in Game 3 of the ALDS against the Yankees.
Cleveland’s lone former Pirate is Austin Hedges, while Colin Holderman is another name worth noting even though he’s no longer available. Holderman would have been in the mix after posting a 2.73 ERA in 54 regular season appearances, but season-ending wrist surgery earlier this month wiped out that possibility.
He came to Pittsburgh from the Mets at the 2022 trade deadline in the Daniel Vogelbach deal and went on to record a 4.39 ERA in 146 appearances, covering 143 2/3 innings out of the bullpen from 2022 through 2025. The Pirates designated him for assignment after the 2025 season, and he signed with the Guardians.
Hedges joined Pittsburgh on a one-year, $5 million deal before the 2023 season. He built his reputation as one of the game’s better defensive catchers, but the bat has usually lagged behind.
That was true in Pittsburgh, where he hit .180/.237/.230 in 185 plate appearances. He was traded to the Rangers at that year’s deadline for international bonus pool money and then won a World Series with Texas.
In Cleveland, he has produced better numbers at the plate, batting .247/.325/.377 with six home runs in 247 plate appearances in 2026. He’s still looking for his first hit this postseason after going 0-for-3 so far.
In Other News...
Bob Nutting Could Finally Face Pressure To Spend More
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For Bob Nutting, the proposal could create a rare kind of pressure to spend, since the Pirates have long operated far below the levels being discussed. A new framework would force clubs like Pittsburgh to rethink how they build, and even by the standards of a sport used to financial haves and have-nots, it would represent a major shift in the expectations placed on ownership. [Read more 🡒]
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But the calculus is not simple, because Mason Montgomery has given the Pirates a real internal option. He has emerged as one of the club's most dependable bullpen pieces, and his closing ability has already made him more than just a fill-in solution. The question now is whether Pittsburgh wants to chase a costly external fix when it may already have a reliever under control who has earned a bigger role. [Read more 🡒]
Pirates Face An Offseason That Will Reveal Ownerships Real Ambition
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The front office has roster work to do, but the bigger question is how much room it will have to operate while trying to keep the team moving forward. The Pirates are in position to make additions and still protect the foundation they have assembled, yet the choices ahead will show whether the plan is to merely stay respectable or to finally treat a playoff push like the expectation. [Read more 🡒]