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Brewers enter World Series ready to etch legacy amid high expectations

Adam RobertsbyAdam Roberts
October 22, 2026, 5:27 pm
in Homepage Showcase, Milwaukee Brewers, News, Sports, Wisconsin
A shot from the field level seats of American Family Field during the 2026 World Series Media Day. October 22, 2026. Image Credit: Adam Roberts

A shot from the field level seats of American Family Field during the 2026 World Series Media Day. October 22, 2026. Image Credit: Adam Roberts

MILWAUKEE, Wis. — As the Milwaukee Brewers prepare to play in their first World Series since 1982, many fans and media members are comparing and contrasting the two teams, as well as the two very distinct eras in baseball history.

To be fair, it makes sense to compare this year’s batch of Brewers to the only other team in franchise history to reach the Fall Classic, and each team was/is composed of a number of unforgettable charachters.

The Miz cracks open Pokémon cards after a dominant outing, while anyone on the pitching staff of Harvey’s Wallbangers was more likely to crack open a few cold ones.

The 2026 bullpen as a unit bolstered the team through the National League Championship Series, while the 1982 pen had to scramble for alternate arms following the late-season injury to star closer Rollie Fingers.

But when thinking about the significance of the Brewers’ return to the World Series, consider for a moment a different year in team history: 2005.

Compared to a team that this year won a franchise-record 103 regular season games, the 81-81 finish accomplished by the ’05 club can seem insignificant. Veterans like Ben Sheets and Geoff Jenkins combined with the young core of J.J. Hardy, Rickie Weeks, and Prince Fielder put together the best non-losing season for Milwaukee since 1992. But in a best-of-seven series against today’s roster with names like Jacob Misiorowski, Christian Yelich, Jackson Chourio, William Contreras, Aaron Ashby and Trevor Megill, the ’05 Brewers would be lucky to salvage a single game.

A key distinction: the expectation for both teams was completely different.

Brewers fans will remember how elated they felt when the ’05 group reached that .500 mark, when all they wanted for the team was just not to lose. The bar now is so much higher, and this year’s World Series berth represents the latest raising of that bar. A whole new generation of young six and seven-year-old Brewers fans only know competitive, winning baseball.

It’s a standard several of this year’s squad said they understood the significance of while speaking to WTMJ during World Series media availability October 22.

“It’s ​cool ​that ​we ​have ​the ​opportunity ​to ​build ​up ​the ​next ​generation ​and ​show ​them ​what ​baseball ​really ​looks ​like,” said Misiorowski, who will be the franchise’s first World Series Game 1 starter since Mike Caldwell threw a complete-game shutout against the eventual champion St. Louis Cardinals on October 23, 1982.

Milwaukee Brewers pitcher Jacob Misiorowski answers questions from the media ahead of the 2026 World Series. October 22, 2026. Image Credit: Elisabeth Montemurro

“Kids ​will ​remember ​this ​as ​they ​get ​older, and ​that’s ​what ​makes ​these ​people fans for life,” added Brandon Woodruff, who has yet to appear on any iteration of the team’s playoff rosters but says he remains optimistic he’ll be added to the World Series edition. ​​”They ​experience ​that, ​and ​​that’s ​all ​you ​want ​to ​experience. Hopefully ​we ​win ​this ​thing and it’s ​a ​memory ​that ​burns ​in ​their ​mind ​for ​the ​rest ​of ​their ​lives.”

Milwaukee Brewers pitcher Brandon Woodruff answers a question from WTMJ’s Adam Roberts at the 2026 World Series Media Day. October 22, 2026. Image Credit: Elisabeth Montemurro

First baseman Andrew Vaughn says the uptick in Brewers buzz across both Milwaukee and Wisconsin has not gone unnoticed by the guys in the clubhouse.

“You ​can ​feel ​the ​buzz ​going ​around,” says Vaughn. “​You ​know, ​driving ​around, ​flags ​are ​flying, ​people ​are ​wearing ​their ​gear. ​It’s ​been ​so ​unbelievable.”

Milwaukee Brewers first baseman Andrew Vaughn takes questions during the 2026 World Series Media Day at American Family Field in Milwaukee, Wisconsin. October 22, 2026. Image Credit: Elisabeth Montemurro

The higher expectations are not limited to the Brewers. Their opponent, the Tampa Bay Rays, for many years was considered a perennial candidate for the AL East basement. Fans of “The Simpsons” may recall Professor Frink comparing the team unfavorably to the study of astrology.

The year that episode aired on FOX? 2005.

In the 21 years since then, the Rays have transformed their identity into a yearly division contender. 2026 marks the franchise’s third World Series berth since ’05, and the team has made the postseason six times since 2019.

Perhaps it’s fitting that the two would meet in the Fall Classic this year, each four wins away from their first title in franchise history. Each ready to raise the standard to an even higher level than before. Each poised to enter the pantheon of the legends of the sport if they can rise up to the moment one last time.

It all begins October 23 at American Family Field, where a sold-out ballpark will be eager to raise their voices as high as expectations have grown to for the hometown nine.

The Milwaukee Brewers are about to have just their second World Series moment. We’ll soon see if 2026 marks the year the bar is raised to a world championship level.

Milwaukee Brewers coverage on WTMJ is sponsored by Potawatomi Casino | Hotel.

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Tags: 2026 World SeriesAndrew VaughnBrandon WoodruffJacob MisiorowskiMilwaukeeMilwaukee Brewerstampa bay raysWisconsinworld series

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