The Pittsburgh Pirates didn't make the playoffs again this season, marking 11 years since they last did. However, there are some former Pirates players who are in the playoffs with a chance to win the World Series.

Ryan Vilade is the lone former Pirate on the Tampa Bay Rays ALCS roster. Vilade never made it on Pittsburgh's MLB roster, spending time in Triple-A with the organization. The 27-year-old has become a solid piece in the Rays lineup, slashing .245/.321/.429 with 11 home runs, eight doubles, three triples, 43 RBIs, 28 runs, and a .750 OPS in 96 games.

Vilade has had five plate appearances for Tampa Bay in the postseason and is 1-for-4 with a home run and a walk.

The Cleveland Guardians only have one former Pirate on the roster: catcher Austin Hedges. Hedges spent 65 games with Pittsburgh in the 2023 season, slashing .180/.237/.230 with one home run, five doubles, 14 RBIs, 13 runs, and a .467 OPS.

He has been much more productive with the Guardians in the 2026 season, slashing .247/.325/.377 with six home runs, 10 doubles, 25 RBIs, 25 runs, and a .702 OPS. Hedges has only had three plate appearances for Cleveland in the playoffs and is 0-for-2 with a walk. One of Vilade or Hedges will make it to the World Series and look to win a ring.

The Los Angeles Dodgers have former Pirates pitcher Tyler Glasnow as one of the key pieces on their NLCS roster. Pittsburgh drafted Glasnow in the fifth round of the 2011 MLB Draft, and he played three seasons for them.

During his time with the Pirates, he posted a 5.79 ERA with 152 strikeouts and a 1.705 WHIP. He never developed into a star with Pittsburgh, but became a great starter with the Rays and has continued to pitch at an elite level with the Dodgers.

In the 2026 season, Glasnow posted a 3.53 ERA with 98 strikeouts and a 0.946 WHIP in 13 starts. Glasnow has made one playoff start for the Dodgers in 2026, going 4.2 innings, allowing one hit, one earned run, and five walks while striking out five.

He will be looking for his third straight World Series ring, and the Dodgers will need a strong outing from him. Their opponent, the Milwaukee Brewers, do not have a former Pirate on the roster.

The Pirates will look to get into the postseason themselves in the 2027 season, while their former players compete for a title.