MLB

Can the Chicago White Sox Make the World Series?

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Sep 19, 2026; Chicago, Illinois, USA; Chicago White Sox center fielder Brenton Doyle (7), outfielder Randal Grichuk (34) and right fielder Braden Montgomery (24) celebrate after defeating the Detroit Tigers at Rate Field. Mandatory Credit: Patrick Gorski-Imagn Images
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On Monday, Aug. 5, 2024, the Chicago White Sox lost their 21st straight game. That brought their record to 27-88, 41.5 games out of first place days into August.

53 days later, the 2024 White Sox became the worst team in modern MLB history, losing its 121st game.

“There are no excuses,” wrote chairman and controlling owner Jerry Reinsdorf to White Sox fans. “This season’s performance was completely unacceptable, and the varying reactions and emotions from our fanbase are completely understandable.”

This franchise hit a low no other organization had ever. In an era of Major League Baseball where talent is evaluated in centimeters, it was thought a team constructed this poorly wasn’t possible.

“You all deserve better,” Reinsdorf said.

In the blink of an eye, just two seasons later, the White Sox are authentically competing for a World Series. The 2026 squad has led the American League Central for most of the season and has played winning baseball through 162 games.

This has defied all odds and predictions. FanGraphs gave them a 0.6% chance to win the division and a cool 0% chance to win the World Series before the season, and the White Sox have become the darlings of 2026.

With the final 10 games of the regular season ahead, Chicago is in a position to bring October baseball back to the South Side. The Sox have unexpectedly been one of the best teams all year and have resupplied hope into a fanbase that recently witnessed an unimaginable rock bottom.

But before the South Siders fantasize about the White Sox in the World Series, they need to make the postseason first.

Sudden Playoff Panic

Chicago began September seven games above .500, with a three-game lead over the Cleveland Guardians. However, through Sept. 16th, the Sox went 5-10 and are now a threat to miss the postseason entirely.

On Wednesday, for the first time since June 10, the White Sox were not tied or in first place in the AL Central. Chicago gave up the division lead to the Cleveland Guardians in a 2-1 series loss.

After winning Game 1, a pair of unexpected heroes emerged for Cleveland. Bryan Rocchio walked off Game 2 with a two-run double, and Petey Halpin hit a go-ahead homer the next day.

Although they gave up the lead, the White Sox still have a real chance to win the division and earn a playoff bye. Chicago holds the tiebreaker over the Guardians, meaning Cleveland would have to finish with a better record.

The White Sox have an easier remaining schedule and still have room to end the season on the right note. However, if things don’t go their way, some AL teams still in the Wild Card hunt could cause trouble.

As of Wednesday, the Texas Rangers, Toronto Blue Jays and Baltimore Orioles have won eight straight combined games. After Thursday’s games, the Rangers and Blue Jays sit just two games back of the final spot, whether that be the Sox or Guardians.

Thankfully for Chicago, they’ve gone 13-7 this season against their final three series opponents. The playoffs and division are still entirely attainable; the White Sox will just need to execute when it matters most.

Making the Dance

Winning the AL Central would give the White Sox a bye in the playoffs. As it stands, the loser will face the winner of the AL West, either the Rangers or the Houston Astros.

That said, the AL West isn’t the division any Central team should fear. That belongs to the American League East.

The Tampa Bay Rays, New York Yankees and Boston Red Sox have been the three best teams in the AL since the Trade Deadline, and it hasn’t necessarily been close. However, this year’s playoff format only allows one of the three to reach the AL Championship Series.

So that sets the stage for the home stretch of 162 games. The AL Central and West are both extremely close races yet to be determined. Also, only three playoff spots remain between the White Sox, Guardians, Astros and Rangers.

Additionally, it will be one of those four teams – unless the Blue Jays or Orioles make a wild jump – facing the AL East representative in the ALCS.

Nothing about the 2026 season has gone to plan, and the final week will be a dramatic telling of that.

A South Side World Series?

If Cleveland wins the Central, the Chi Sox will play the Astros or Rangers in a three-game Wild Card series. The AL West has been by far the worst division of the year, and still holds the possibility of having the first sub-.500 team win a division.

The 2005 San Diego Padres are the worst division winner in league history, finishing 82-80. As of Sept. 17, Houston is 77-76, and Texas is 76-77.

Although the White Sox will be on the road for that Wild Card series, they should win it regardless. In any other playoff format or version of 2026, the Rangers and Astros shouldn’t be brought up in playoff conversations.

If it’s the Rangers, expect a swift White Sox victory. But there’s a world where the Astros cause a headache. Chicago is 2-5 against the Astros this season, and Houston’s playoff experience could best the young Sox in a short series.

But overall, no team from the West should be a reason for concern. If they end up facing the Guardians in the best-of-five Division Series, this should also be a White Sox win. For years, Cleveland has been a pest for opponents in the regular season, but hasn’t won in October.

With all of this said, an AL East team must be beat to reach the World Series. This is where the White Sox lose their edge. Against the Rays, Yankees and Red Sox, Chicago’s gone a combined 5-14.

This is where South Siders must put their faith in the unpredictability of the sport of baseball. No statistic or advanced metric can capture a team’s magic and mojo. No stat can tell you that a 121-loss team would make the playoffs two years later.

Everyone involved with the White Sox must cling to one idea: crazier things have happened.

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