How Long Will The Brewers World Series Contention Window Be Open?

Every time a baseball team, especially a small market team like the Milwaukee Brewers, enters a competitive window where they have a legit chance to win the World Series, the question of how long that window will be open is always in the back of every fan’s mind.

For many, they believe the window to win it all is closing rapidly, whether is actually is or not. There’s a sense of urgency as small market fans know their chances are few and far between to win it all. The Brewers themselves still have never won a World Series. They had some chances in the 1980s, then didn’t have any for a number of years. Then there was late 2000s and early 2010s with a couple chances.

Now, of course, the Brewers have made four straight postseasons and have come up short of the ultimate goal in all of them. Milwaukee has not had a sustained level of success for this long before, so the natural feeling among many fans is that this window is going to close at any moment.

But is that actually the case here?

Just how close to closing is the Milwaukee Brewers’ window to win a World Series with this roster’s core?

Thankfully, David Stearns is at the helm in the front office and he’s made a stated goal to keep this franchise continually competitive and not just going into up and down cycles every five years or so. So far, he’s been achieving that goal.

The four straight playoff appearances is the longest stretch in franchise history and there’s no sign of it slowing up anytime soon.

The foundation of this team is under contract. Christian Yelich is here through 2028 at least and Freddy Peralta is under contract potentially through 2026 at an inexpensive rate. Those are the Crew’s two long-term contracts so far, but there are more pieces to this foundation.

Lorenzo Cain and Omar Narvaez are the key free agents after 2022, but the Brewers can replace those two from prospects within the organization already and still be good. Josh Hader is a free agent after 2023, as is Brent Suter, Kolten Wong, and Hunter Renfroe. Those guys will be tough losses if they aren’t re-signed but the Brewers also have replacements coming up in the outfield and Devin Williams could take over the closer’s role.

The bulk of this team’s foundation will be here through at least 2024. That includes Cy Young winner Corbin Burnes, Brandon Woodruff, Willy Adames, Adrian Houser, and Eric Lauer. That’s 80% of the current starting rotation and the Crew’s star starting shortstop.

Meanwhile, Rowdy Tellez, Luis Urias, and Devin Williams are under team control through 2025.

Based on the roster of this group and when they’re all slated to reach free agency, the Milwaukee Brewers World Series window runs through at least 2024. That gives the Brewers three more seasons and three more really good shots at winning a title.

Granted, this could change and get extended as time goes on. Some core players could sign contract extensions, while some prospects could come up and immediately replace any departing key contributors. Those young players are under team control for six seasons.

That means guys like Aaron Ashby and Ethan Small will be here for several years more to fill out that rotation, and several other prospects like Garrett Mitchell, Joey Wiemer, Mario Feliciano, Brice Turang, and others will be here for a while and can extend that contention window by playing well.

When it comes to the Brewers contention window, it’s open at least through the 2024 season right now. Don’t count out David Stearns prolonging that window by working his magic as well. When this window started, many thought it would’ve ended by now, yet here we are.

Every season the Brewers come up short, fans will complain the window is rapidly closing as another chance got wasted. But don’t fret, the window isn’t closing that quickly, and it can always be propped back open.