Pirates Next Playoff Appearance Could Look Very Different

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PITTSBURGH — The Pittsburgh Pirates are aiming for postseason baseball in 2027, but it could look a lot different from how it is today.
MLB sent out a proposal to change the playoffs starting next season, with two major changes from 2026, but still keeping the same 12 teams, six from the American League and six from the National League.
It includes making the Divisional Series go from a best-of-five series to a best-of-seven series, as part of the reduction of eight games in the regular season, from 162 to 154, starting with the 2029 season.
The highest-seeded teams would also pick their opponents in the Wild Card and Divisional Series, instead of the current bracket system.
How Does This Impact the Pirates?
The Pirates haven't made the postseason since 2015, but they did clinch their first winning season since 2018, with an 82-80 record.
Pittsburgh should get closer to postseason contention in 2027, and if they make the right moves this offseason, they could finally play meaningful baseball in October once again.

The Pirates would find themselves in a tough position, assuming they just clinch a spot in the NL Wild Card.
If they clinched the final spot, they would most likely face the third seed, the lowest NL division title winner, in the NL Wild Card and then the first seed in the NLDS.
The current system is a bracket, where the sixth seed would face the third seed in the Wild Card round, but then face the second seed in the Divisional Series.
Pittsburgh would likely struggle with these changes, but could benefit if they end up being one of the better teams in the NL in 2027.
Why is MLB Making This Proposal Public?
The current collective bargaining agreement expires at midnight on Dec. 2, and if a new one isn't signed, the owners will lock out the players, potentially resulting in games being lost or the 2027 season not occurring.
The owners are looking to implement a salary cap, something the players' union, MLBPA, has historically been against and went on strike during the 1994 season over it, cancelling the World Series.

MLBPA released a statement on the proposal, saying that the players will review it and respond at the bargaining table, but that this also comes with a salary cap, which the union made known their stance on it specifically.
Statement on today’s bargaining session pic.twitter.com/Z87gm778J1
— MLBPA (@MLBPA) October 8, 2026
MLB wants more postseason games, as 2029 should be the first year for new national media contracts, where they can make more money from television and other streaming revenue, per Evan Drellich of The Athletic.
More postseason games mean more money, so erasing the eight regular season games and adding more playoff games should lead to better revenue for MLB.
MLBPA will likely be skeptical of players losing money from the eight games lost, especially with the introduction of a cap system
Both sides have less than two months until the CBA expires and it's not looking like they'll get anything signed quickly.

Dominic writes for Pittsburgh Pirates On SI, Pittsburgh Panthers Pn SI and also, Pittsburgh Steelers On SI. A Pittsburgh native, Dominic grew up watching Pittsburgh Sports and wrote for The Pitt News as an undergraduate at the University of Pittsburgh, covering Pitt Athletics. He would write for Pittsburgh Sports Now after college and has years of experience covering sports across Pittsburgh.