David Bednar's free agency creates awkward dilemma for Pirates after Mason Montgomery breakout

The Pittsburgh Pirates have an opportunity to bring back one of their most beloved players this offseason. Unfortunately for David Bednar, they might have already found his replacement.

Bednar is set to hit free agency following another impressive season with the New York Yankees, creating an intriguing possibility for a reunion with his hometown team. But after Mason Montgomery's remarkable second-half emergence, Pittsburgh suddenly has a much more complicated decision to make.

Bednar, whom the Pirates traded to New York at the 2025 deadline, finished the 2026 regular season with a 2.47 ERA, 35 saves and 76 strikeouts across 69 1/3 innings. The two-time All-Star has firmly reestablished himself as one of baseball's most reliable late-inning relievers, and his performance should make him an attractive target for teams seeking bullpen stability.

Pittsburgh certainly fits that description. The Pirates endured another frustrating season of bullpen inconsistency, particularly during the first half, when blown leads repeatedly undermined an otherwise talented roster.

But Montgomery's emergence changed the equation considerably.

Acquired from Tampa Bay in the December 2025 trade that also brought Brandon Lowe to Pittsburgh, Montgomery developed into one of the Pirates' most important bullpen weapons. The 26-year-old left-hander finished with a 2.88 ERA, 105 strikeouts in 68 2/3 innings and 18 saves.

His September performance was especially impressive. Montgomery converted 11 of 12 save opportunities while posting a 2.08 ERA, earning National League Reliever of the Month honors. He also assembled a remarkable streak of 24 2/3 consecutive scoreless innings.

Ironically, the last Pirates reliever to win that monthly award was Bednar in June 2025.

Now Pittsburgh must decide whether spending significant money to bring Bednar home makes sense when Montgomery has already demonstrated that he can handle ninth-inning responsibilities.

Mason Montgomery's emergence, David Bednar's free agency will test how serious Pirates are about building a winning bullpen

Make no mistake: Bednar won't come cheap.

Entering his age-32 season, the veteran right-hander figures to attract considerable interest in free agency, including potentially from the Yankees themselves. A multiyear commitment to an established closer would represent a significant financial investment for an organization that has historically avoided expensive relief contracts.

Montgomery, meanwhile, remains under affordable team control, giving the Pirates an opportunity to allocate their limited financial resources toward more pressing needs.

However, having a legitimate closer already on the roster shouldn't automatically eliminate Pittsburgh from the Bednar conversation.

The Pirates won 82 games in 2026 but still missed the postseason. They need bullpen depth, not merely someone capable of recording the final three outs. A late-inning combination featuring Montgomery from the left side and Bednar from the right would provide manager Don Kelly with considerable flexibility.

Of course, a reunion remains unlikely if Bednar's market develops as expected. The Pirates have other roster holes to address, and spending heavily on an aging reliever carries legitimate risk. But Montgomery's breakout shouldn't become another convenient excuse for ownership to avoid meaningful investment.

The Pirates finally have a young, affordable closer worth building around. The question is whether they'll use that advantage to strengthen the rest of their bullpen or simply declare the position solved and pocket the savings.

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