The Chicago White Sox have gone from an all-time embarrassment to a team stacking October wins, and that should sting in Pittsburgh.
Two years after losing 121 games - the most by any MLB team in the Modern Era - Chicago is suddenly one win away from the ALCS. The White Sox finished the 2026 regular season 84-78, became the first club in league history to reach the postseason right after at least two straight 100-loss seasons, then kept rolling by sweeping the Houston Astros in the Wild Card round for their first postseason series win since 2005.
They didn’t stop there. In Game 1 of the ALDS, the White Sox beat the Cleveland Guardians 3-0, powered by Munetaka Murakami’s two-run homer and a pitching staff that limited Cleveland to three hits. Chicago now leads the best-of-five series 1-0.
The White Sox are such a vibe. 😂 pic.twitter.com/VuM9QcrgTC
- Foul Territory (@FoulTerritoryTV) October 3, 2026
For the Pirates, the contrast is brutal. Pittsburgh finished 82-80, its first winning season since 2018, and that matters.
It was real progress after years of losing. But the Pirates still missed the postseason by six games, and their year ended Sept. 27 while Chicago’s kept going.
No one should pretend the two rebuilds were identical. Different markets, different rosters, different injuries, different divisions - all of that matters. But Pirates fans have heard the same basic explanation cycle for nearly all of Ben Cherington’s run: be patient, trust the process, wait for the prospects, let the pitching develop, hope the hitters arrive, and believe the payoff is coming.
Cherington arrived after the 2019 season. Since then, Pittsburgh has sold the idea that if it tore things down, stockpiled talent and stayed disciplined, sustainable winning would eventually follow. Seven seasons later, the return is 82 wins and an October spent on the couch.
Chicago just showed how fast things can turn when a team actually moves once the young core starts to hit.
And this wasn’t some fluky veteran surge. The 2026 White Sox looked nothing like the 2024 group that went 41-121, and players who appeared for both teams accounted for only 19.8% of Chicago’s plate appearances this season. That’s a real reset.
That’s what a rebuild is supposed to be: identify the parts that aren’t working, replace them, and keep pushing.
The Pirates, meanwhile, have often treated time like a strategy. One more year for a prospect.
One more offseason to sort out a position. One more deadline where the price wasn’t right.
One more winter where payroll constraints narrowed the menu. One more season where progress was promised for later instead of demanded now.
Pittsburgh did make progress in 2026. The offense improved, the club finally got above .500, and the roster no longer looks hopeless.
But the White Sox have made the bigger point: progress is not supposed to be the finish line. Eventually, you have to win.
Chicago climbed from 41-121 in 2024 to 84-78 in 2026, a 43-win jump in two seasons. Pittsburgh just wrapped up Year 7 under the same general manager and still has not played a postseason game in that span. That’s the uncomfortable comparison.
The White Sox hit a lower low than the Pirates ever did during this stretch. They were historically bad, then got worse before getting good.
That kind of rise should have been enough to settle for respectability. Instead, they’re two wins from the ALCS.
For Pittsburgh, the message from Chicago is clear. The excuses are running out.
The pitching is there. The offense has finally shown life.
Now the mandate for 2027 is simple: finish the job.
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According to Ballpark Pal, Reynolds was the unluckiest home run hitter in baseball in 2026, with an estimated 8.2 homers taken away by stadium and weather effects. Playing half his games at PNC Park, where the dimensions can be especially unfriendly to right-handed batters, helped explain why some of those well-struck balls never became souvenirs, and it leaves Pirates fans wondering what his totals might have looked like in a more forgiving setting. [Read more 🡒]
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For Pirates fans, it carried an uncomfortable reminder of those late-season bullpen games in Pittsburgh, only theirs came out of necessity rather than design. Injuries and a shortage of healthy starters forced the Pirates into that kind of scramble, so watching Atlanta use the same approach to even a division series only sharpened the contrast between a planned postseason tactic and a roster reality the Pirates spent months trying to manage. [Read more 🡒]
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What makes the conversation interesting is that so much of the planning still hinges on one big unknown: how the group settles in once everyone is healthy and the roles sort themselves out. Pittsburgh has the makings of a deep staff, but the difference between a promising rotation on paper and one that carries the club is often a matter of timing, health and whether the right arms line up when the season matters most. [Read more 🡒]