Pirates Facing Cruel Reality as Playoffs Transpire

The Pirates had higher payrolls than all the AL teams remaining in the postseason, with the White Sox at $103 million and 24th, the seventh-lowest, the Rays at $96 million, the third-lowest, and the Guardians at $74 million, the lowest in baseball.

Milwaukee finished with a higher payroll than Pittsburgh, $146 million, but that was still the 19th-highest and nowhere near the top.

The Los Angeles Dodgers, who the Brewers will face in the NLDS, have the second-highest payroll, $339 million, and are the "villains" of baseball, going for their third straight World Series.

Pirates Pale in Comparison to Fellow Small Market Teams

The Pirates have been one of the worst teams in baseball in the past few decades, including their 20 straight losing seasons from 1993 to 2012, a North American professional sports record.

Pittsburgh has just five winning seasons, including 82-80 in 2026, and three postseason appearances, 2013-15, in the past 34 seasons.

All the other teams, despite only the White Sox winning the 2005 World Series, haven't reached the precipice; they've been much better teams than the Pirates and far more successful.

The Rays are an expansion team, starting play in 1998, and have made the postseason 10 times since 2008, with five AL East Division Titles and two pennants in 2008 and 2020.

Pittsburgh even made a great trade with Tampa Bay last offseason, landing second baseman Brandon Lowe, left-handed relief pitcher Mason Montgomery and outfielder Jake Mangum, but they are four games away from playing in their third-ever World Series.

The White Sox have four AL Central titles and two Wild Card berths this century, but have also been terrible this decade, dealing with an ugly rebuild.

Chicago's South Side ball club went from 41-121 in 2024, the most losses ever by an AL team, to 60-102 in 2025 and then 84-78 and a Wild Card berth in 2026.

The Guardians have made the postseason 16 times, won the AL Central 14 times and made the postseason three times, 1995, 1997 and 2016 over the past 34 years compared to the Pirates.

Milwaukee, like Tampa Bay, has made the postseason 10 times since 2008, winning the NL Central seven times, including five times this decade and the past three seasons.

Is the Future Bright For Pittsburgh?

It's tough for the Pirates to look at their small market counterparts, all of whom have had great success and look primed to keep having it in the future.

Pittsburgh is building towards that, with a strong and young starting rotation, a formidable lineup and a bullpen that could be great with some additions.

The Pirates spent most of the season in the NL Wild Card race and bounced back from a poor 7-16 stretch from late July to mid-August to finish with a winning record.

Pittsburgh will need to build its roster for next season, and if they do that well and the stars stay healthy compared to 2026, the 2027 campaign could be the year they compete in October.