The 2026 MLB Postseason, Ranked by World Series Championship Drought

Twelve teams have reached the 2026 MLB postseason. The teams range from include the longest draught to the reigning back-to-back champions. The Los Angeles Dodgers are trying to win their third consecutive championship, something Major League Baseball has not seen since the New York Yankees won three straight from 1998 through 2000.

The Cleveland Guardians are trying to win their first since 1948. The Milwaukee Brewers, San Diego Padres and Tampa Bay Rays have never won one at all.

And then there are my Milwaukee Brewers.

The Brewers finished 2026 with the best record in baseball at 103-59, earning the National League's No. 1 seed. The Dodgers finished 100-62 and took the No. 2 seed, meaning the two teams cannot see each other again unless both reach the NLCS. The Dodgers have become Milwaukee's newest postseason nemesis. The Brewers swept all six regular-season meetings against Los Angeles in 2025 before the Dodgers returned the favor when it mattered, sweeping Milwaukee out of the NLCS. Los Angeles went on to beat Toronto in seven games to win its second consecutive World Series.

Milwaukee came back in 2026 and won four of seven against L.A. during the regular season.

So yes, give me another Brewers-Dodgers NLCS. Give me the franchise that has kept Milwaukee waiting since 1970 for its first championship against the franchise trying to become baseball's first three-time defending champion in 26 years. Give me Milwaukee ending its drought by slaying the team that ended its season one year ago. Let's avenge that game 7, NLCS home loss in 2018. Bring Robin Yount and Paul Molitor back to throw out the first pitches.

But before we get there, here are all 12 postseason teams ranked by how long they have been waiting to win the World Series.

1. Cleveland Guardians — Last Championship: 1948

Championship drought: 78 years

Last World Series appearance: 2016

No team left standing has waited longer.

Cleveland won the World Series in 1948 and has been waiting ever since. The franchise has returned to the World Series four times — 1954, 1995, 1997 and 2016 — without winning it.

The closest call came in 2016. Cleveland took a 3-1 series lead over the Chicago Cubs before losing three straight, including a 10-inning Game 7. That night ended one historic drought and extended another. The Cubs finally won after 108 years. Cleveland's wait continued.

A Guardians championship in 2026 would end a drought that has lasted nearly eight decades.

2. Milwaukee Brewers — Never

Championship drought: 57 completed seasons entering 2026

Last World Series appearance: 1982

This is the one.

The franchise began as the Seattle Pilots in 1969, moved to Milwaukee one year later and has never won the World Series.

It has played in one.

The 1982 Brewers — Harvey's Wallbangers — reached Game 7 of the World Series against the St. Louis Cardinals before losing 6-3.

That remains Milwaukee's only appearance in the Fall Classic.

The Brewers have come close since. They took the Dodgers to Game 7 of the 2018 NLCS. They returned to the NLCS in 2025 after posting baseball's best regular-season record, only to run straight into the Dodgers again.

That one hurt in a different way.

Milwaukee had beaten Los Angeles in all six regular-season games. Then the postseason began, and the Dodgers swept the Brewers in four games while holding Milwaukee to one run in each game.

Then L.A. won the World Series.

Now we have 2026.

Milwaukee again finished with baseball's best record. The Brewers again have the Dodgers sitting on the other side of the National League bracket. And this time Los Angeles arrives as the two-time defending World Series champion, trying to accomplish something nobody has done since Derek Jeter, Mariano Rivera and the Yankees at the turn of the century.

If Milwaukee is going to win its first World Series, why take the easy route?

Beat the Dodgers.

End their dynasty bid.

Avenge 2025.

Then go win the damn thing.

3. San Diego Padres — Never

Championship drought: 57 completed seasons entering 2026

Last World Series appearance: 1998

The Padres entered the National League in 1969, the same year the Brewers franchise began in Seattle.

Neither has won a World Series.

San Diego has at least reached it twice. The Padres lost to the Detroit Tigers in 1984 and ran into the Yankees' budding dynasty in 1998.

The Yankees swept that World Series and went on to win again in 1999 and 2000.

Twenty-eight years later, San Diego is still searching for its first championship.

4. Tampa Bay Rays — Never

Championship drought: 28 completed seasons entering 2026

Last World Series appearance: 2020

The Rays are the youngest franchise among this year's title-less playoff teams.

Tampa Bay began play in 1998 and has already won two American League pennants.

The first ended with a loss to Philadelphia in the 2008 World Series. The second ended with a loss to the Dodgers in 2020.

The Rays now have another shot at championship No. 1.

5. Chicago White Sox — Last Championship: 2005

Championship drought: 21 years

Last World Series appearance: 2005

There was a time when 21 years would have sounded adorable to White Sox fans.

Before 2005, they had gone 88 years without winning the World Series.

Then came one of the greatest postseason runs in franchise history. Chicago swept Houston in the World Series and ended the drought. The strange part is what happened next: the White Sox haven't been back.

So the franchise that once waited from 1917 to 2005 has now gone another 21 years without even appearing in the Fall Classic.

6. Philadelphia Phillies — Last Championship: 2008

Championship drought: 18 years

Last World Series appearance: 2022

Philadelphia's last championship came in 2008, when the Phillies defeated Tampa Bay.

They returned to the World Series the following year and lost to the Yankees, then made it back in 2022 before losing to Houston. The Phillies have therefore won a pennant within the past four years. It is the championship that has eluded them since 2008.

7. New York Yankees — Last Championship: 2009

Championship drought: 17 years

Last World Series appearance: 2024

Seventeen years is hardly historic by baseball standards. For the Yankees, it practically qualifies as an ice age. New York won championship No. 27 in 2009. The Yankees returned to the World Series in 2024 but lost to the Dodgers in five games. And there is another reason the Yankees are part of the story this October.

They still own the last three-peat. The Yankees won the 1998, 1999 and 2000 World Series. No team has won three consecutive championships since. The Dodgers enter this postseason trying to become the first.

8. Chicago Cubs — Last Championship: 2016

Championship drought: 10 years

Last World Series appearance: 2016

For 108 years, the Cubs owned baseball's most famous championship drought.

Then came 2016. Chicago came back from a 3-1 World Series deficit and defeated Cleveland in 10 innings of Game 7, winning its first championship since 1908. Ten years have passed. Compared with what Cubs fans once endured, that's practically yesterday.

9. Boston Red Sox — Last Championship: 2018

Championship drought: 8 years

Last World Series appearance: 2018

Boston broke its own legendary 86-year drought in 2004 and then kept winning. No curse, just lousy teams for 8 decades. The Red Sox added championships in 2007, 2013 and 2018.

Their most recent one came against the Dodgers, whom Boston defeated in five games in the 2018 World Series. Eight years later, they're back in October.

10. Atlanta Braves — Last Championship: 2021

Championship drought: 5 years

Last World Series appearance: 2021

Atlanta defeated Houston in six games to win the 2021 World Series.

It was the Braves' first championship since 1995 and the franchise's fourth World Series title overall.

Five years later, Atlanta gets another shot.

11. Houston Astros — Last Championship: 2022

Championship drought: 4 years

Last World Series appearance: 2022

Houston's last trip to the World Series was also its last championship.

The Astros defeated Philadelphia in six games in 2022.

Four years isn't much of a drought.

Then again, there is one team in this postseason that would consider four years an eternity.

12. Los Angeles Dodgers — Last Championship: 2025

Championship drought: Technically one year, if you insist on calling that a drought

Last World Series appearance: 2025

Oh, these poor people. The Dodgers won the 2024 World Series. Then they won the 2025 World Series. Now they would like another one.

Los Angeles became baseball's first repeat champion since the Yankees completed their three-peat in 2000. A third consecutive Dodgers title would make them only the third franchise in baseball history to win at least three straight, joining the Yankees and Athletics.

No thanks.

I have another ending in mind.

Milwaukee and Los Angeles finished with the two best records in the National League — in fact, the two best records in all of baseball. The Brewers won 103 games. The Dodgers won 100.

They can't meet before the NLCS.

Perfect.

Let somebody else handle the Wild Card round. Let Milwaukee take care of its Division Series. Let Los Angeles survive its side of the bracket. Then give us the rematch. In 2025, Milwaukee went 6-0 against the Dodgers when it didn't matter enough and 0-4 when it mattered most. In 2026, the Brewers won the season series again. Now finish the story. Beat Los Angeles when it counts. Stop the first attempted World Series three-peat since the Yankees. Win the National League pennant for the first time in 44 years.

And then, after a franchise history that began with the Seattle Pilots in 1969, after 1982, after 2018, after the 2025 sweep, after all of it: