MLB's proposed playoff overhaul could create another hurdle for Pirates' postseason dreams

Imagine the Pittsburgh Pirates finally ending their postseason drought, only to have a higher-seeded opponent publicly select them as the team it would rather face in October.

Under Major League Baseball's proposed playoff overhaul, that scenario could become a reality as soon as 2027. And for a franchise that has spent years trying to assemble a roster capable of reaching the postseason, the potential changes raise an uncomfortable question: Are the Pirates building a team that can actually compete in October, or merely one capable of getting there?

MLB has proposed several significant changes to its postseason structure as part of ongoing collective bargaining negotiations. One of the proposed changes beginning in 2027 is that the No. 3 seed in each league would select whether to face the No. 5 or No. 6 seed in the Wild Card Series. The No. 1 seed would subsequently choose its Division Series opponent from the Wild Card winners.

Additional changes would arrive in 2029, including reducing the regular season from 162 games to 154 and expanding the Division Series from a best-of-five to a best-of-seven format.

None of these changes is guaranteed. MLB has tied its proposals to a broader collective bargaining agreement involving a salary cap, which the players' union has strongly opposed. Nevertheless, the proposed changes are worth examining from Pittsburgh's perspective, particularly because they could fundamentally alter what it takes to make a meaningful postseason run.

Pirates' pitching-heavy approach could face a tougher October test

For years, the Pirates' rebuilding strategy has revolved around accumulating talented young pitchers and hoping the offense eventually catches up.

That approach produced tangible progress in 2026. Pittsburgh finished 82-80, securing its first winning season since 2018. The offense made considerable strides, and Paul Skenes, Jared Jones, Braxton Ashcraft and Bubba Chandler emerged as the foundation of a potentially formidable rotation.

In a short postseason series, that kind of pitching talent can be particularly dangerous. An ace can steal a game, and a timely offensive performance can swing an entire series. But expanding the Division Series to seven games could expose weaknesses that are easier to disguise in a shorter matchup. Longer series create more opportunities for opponents to exploit inconsistent lineups, unreliable middle relief and insufficient roster depth.

Granted, MLB's proposal also includes additional postseason off-days that could allow teams to use their best pitchers more frequently. Still, Pittsburgh's bullpen remains a concern. Mason Montgomery emerged as a legitimate late-inning weapon, but Gregory Soto is approaching free agency, Kirby Yates has retired, and several relief roles remain unsettled.

The Pirates have the starting pitching talent to make themselves dangerous in October. Whether they have enough talent surrounding those starters to survive multiple rounds is another question entirely.

MLB's proposed changes would reward teams the Pirates are still chasing

The proposed opponent-selection system presents another interesting wrinkle. Allowing higher seeds to choose their matchups would introduce an additional advantage for teams that finish near the top of the standings.

Under the proposed system, Pittsburgh could finally secure a Wild Card berth only to find itself selected by an opponent that believes it represents the most favorable matchup. Postseason upsets happen, of course, but the proposal reinforces the importance of building a team capable of competing for a higher seed rather than simply hoping to sneak into the playoff field.

Perhaps the most frustrating part of this discussion is that the Pirates already possess several pieces necessary to build a legitimate contender. Skenes gives Pittsburgh a frontline starter capable of anchoring a postseason rotation. Jones, Ashcraft and Chandler provide additional upside, while Konnor Griffin represents a potential cornerstone of the offense.

But the supporting cast remains a work in progress. Brandon Lowe's impending free agency threatens to remove one of the lineup's most productive hitters. Questions persist at multiple positions, and the bullpen needs more reliable depth.

An 82-win season was an encouraging development after years of disappointment, but it wasn't proof that the rebuild is finished. And whether MLB ultimately adopts its proposed postseason changes or maintains the existing structure, the responsibility facing Cherington remains the same.

The Pirates need to build a team capable of winning a championship, not simply one that might finally receive an invitation to compete for it. And if MLB's proposed overhaul becomes reality, the consequences of failing to make that distinction could become even more apparent.

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