White Sox’s stunning playoff run makes Pirates’ endless rebuild look even worse

The Chicago White Sox lost 121 games two years ago. It was the most losses by an MLB team in the Modern Era, the kind of season that ordinarily becomes shorthand for organizational incompetence for decades.

Somehow, things barely looked better a year later. Chicago lost another 102 games in 2025, its third consecutive season with at least 100 losses.

Now the White Sox are winning playoff games. And if you're a Pittsburgh Pirates fan, that should be more than a little infuriating.

Chicago finished the 2026 regular season 84-78, becoming the first team in MLB history to reach the postseason immediately following at least two consecutive 100-loss seasons — and the White Sox had actually done it three years in a row. Then they stopped treating merely getting there like the accomplishment.

The White Sox swept the Houston Astros in the Wild Card round for their first postseason series victory since 2005. Then, in Game 1 of the ALDS, they shut out the Cleveland Guardians, 3-0, behind Munetaka Murakami's two-run homer and a pitching staff that held Cleveland to three hits. Chicago now has a 1-0 lead in the best-of-five series.

Meanwhile, the Pirates are at home celebrating progress. Pittsburgh finished 82-80 this season, its first winning record since 2018 and an undeniably meaningful step forward after years of losing. But the Pirates still finished six games out of a Wild Card spot. Their season ended Sept. 27. Chicago's didn't.

Nobody should pretend the two organizations followed identical paths or operated under identical circumstances. Rebuilds are messy. Prospects develop at different rates. Injuries happen. Divisions have different levels of difficulty. Some moves work, some don't. But Pirates fans have heard some version of those explanations for almost the entirety of Ben Cherington's tenure.

Cherington took over after the 2019 season. Since then, Pittsburgh has repeatedly asked its fan base to be patient while it tore down, accumulated prospects, developed pitching, waited for young hitters, supplemented the roster around the edges and insisted the foundation was eventually going to produce sustainable winning. Seven seasons later, the reward was 82 wins and watching October baseball from home.

The White Sox just demonstrated how quickly the standard can change when an organization actually accelerates once its young core begins to emerge.

White Sox are proof that rebuild timelines are choices, not laws of nature

What's especially uncomfortable for Pittsburgh is that Chicago's turnaround wasn't built around one miraculous veteran roster somehow catching fire. The 2026 White Sox barely resemble the historically terrible 2024 team. Players who appeared for both clubs accounted for only 19.8% of Chicago's plate appearances this season.

That's what rebuilding is supposed to look like. Identify what isn't good enough, replace it, and keep moving.

Too often, the Pirates have treated time itself like part of the development plan. Another year for this prospect. Another offseason to evaluate that position. Another deadline where the price wasn't right. Another winter where ownership's financial limitations conveniently narrowed the available options. Another season in which meaningful progress was promised for the future rather than demanded in the present.

The Pirates finally did make progress in 2026. They scored substantially more runs and finally dragged themselves above .500. But the White Sox are a reminder that progress and patience aren't supposed to become permanent goals. Eventually, you're supposed to win.

Chicago went from 41-121 in 2024 to 84-78 in 2026 — a 43-win improvement in two seasons. Meanwhile, the Pirates just completed Year 7 under the same general manager and still haven't played a postseason game during his tenure. That's the part Pittsburgh should find embarrassing.

The White Sox hit a lower bottom than the Pirates ever did during this rebuild. They were historically bad. They followed that historically bad season by losing 102 more games. Their situation looked hopeless enough that simply getting back to respectability in a few years would've represented legitimate progress. Instead, they're two wins away from the ALCS.

Pittsburgh, by comparison, has spent years treating incremental improvement as evidence that everyone just needs to remain patient a little longer. There shouldn't be another grace period now.

The Pirates have young pitching throughout the organization and finally showed enough offensive improvement to prove this roster isn't hopeless. That should make the 2027 mandate incredibly simple: finish the job.

Spend to retain or replace Brandon Lowe's production. Add legitimate major-league offense. Build enough rotation depth that bullpen games aren't a necessity. Stop treating external additions like luxuries and start treating them like the cost of trying to win.

Chicago went from historically awful to October dangerous in two years. After seven years of waiting, Pirates fans shouldn't be asked for an eighth.

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