Predicting where each free agent from the Brewers' 2026 World Series winning roster will sign

The MLB season has been over for nearly two weeks, and while the state of Wisconsin is still celebrating the Milwaukee Brewers' first World Series title, the eyes of those in charge are already shifting to the 2027 season. Milwaukee has already made a series of roster decisions, including electing to exercise their club option on World Series MVP, William Contreras.

The team also extended the qualifying offer to NLCS MVP Jake Bauers, while watching Brandon Woodruff, Gary Sánchez, Dustin May, JoJo Romero, Antonio Senzatela, Bryse Wilson, and Jared Koenig all reach free agency through various methods.

Counting Bauers, who still has a week to accept or decline the qualifying offer, the Brewers have eight departing free agents. While Milwaukee isn't typically known for landing a big-name free agent, or even retaining a lot of their own talent due to financial restraints, there is a degree of pressure for the team to bring back as many members from the World Series team to try to repeat, and supposedly they have the money to bring at least a few back. With that in mind, let's take a look into our metaphorical crystal ball and see where the Brewers' departing free agents are playing next year.

Predicting where Brewers' 2026 free agents will sign this offseason

1B/OF Jake Bauers: Milwaukee Brewers

Anyone who caught a Brewers postseason game was frequently reminded of the fact that Bauers was almost done with baseball after the 2024 season, but chose to come back for health insurance after finding out his wife was pregnant, a report initially from Curt Hogg of the Milwaukee Journal Sentinel. The decision paid off for both Bauers and the Brewers, as his breakout 2026 season was a large reason key to Milwaukee's record-breaking regular season and World Series run.

As a result, Bauers is due to cash in on his strong 2026 season in free agency. He has the $23.15 million qualifying offer from the Brewers if his initial free agent negotiations don't go as he hopes they will, but it's likely Bauers will earn more on the free agent market. The Brewers aren't typically in the business of paying players at the peak of their career, but they may make an exception for the only LCS MVP in franchise history. After all, the fact that Bauers was offered a qualifying offer means that any team who ends up signing him would have to forgo draft capital in order to do so, which could shrink his market and help the Brewers' negotiating power. Then again, Milwaukee may not want to surrender the draft capital themselves.

If Bauers' market comes down to around two years, $40 million, assuming he declines the qualifying offer, the Brewers should seriously entertain bringing the breakout slugger back. Such a deal would likely result in the Brewers trading Andrew Vaughn and having prospect Luke Adams serve as the right-handed complement to Bauers for the next two seasons.

RHP Brandon Woodruff: Milwaukee Brewers

Brandon Woodruff has been one of the biggest "what if?" stories in baseball over the past several seasons, but Woody's journey has a chance to have a fairytale ending. Once one of the premier pitchers in baseball, a shoulder injury derailed Woodruff's season ahead of the 2023 postseason, and he has yet to regain form. The 2026 season hoped to be the one to get the ace back on track, but more shoulder injuries flared up, and after another trip to the IL after losing his velocity on July 4th, Woodruff's season seemed over.

Of course, we know how this story ends. He didn't require the surgery that was initially anticipated, and he was able to pitch the final inning of Milwaukee's Game 3 blowout of the Rays. The Brewers' longest tenured player got the chance to finish the story, and helped his team get its first ring in franchise history.

Following a sequence of events like that, and with the injury history Woodruff possesses, retirement is certainly a possibility for the soon-to-be 34-year-old. However, Woodruff sure doesn't seem like he's ready to hang up the spikes. As a result, it's possible the Brewers give their franchise icon a reasonable one-year deal to see if Woodruff has anything left in the tank. It's not really in the Brewers' character to make such a move, but at the right price, bringing Woodruff back for another season is certainly justifiable.

RHP Dustin May: Detroit Tigers

Dustin May opted for free agency before the Brewers' World Series parade got underway, declining the $20 million mutual option that he had pending. In all likelihood, Milwaukee would have declined it as well, so May gets to save face and hit the open market right away instead of waiting to see what the Brewers brass would decide.

There is a slight argument that could be made for May declining the option in order to sign a team-friendly deal to return to Milwaukee, but for all intents and purposes, it doesn't really make sense for either side. Instead, Dustin May should look to capitalize on being a World Series champion on the open market, after proving to be an intriguing, albeit inconsistent, mid-rotation starter.

Detroit lost Tarik Skubal at the trade deadline and seemingly doesn't have plans to re-sign the 2x Cy Young Award winner, but they still enter the 2027 campaign with a chance to contend for an AL Central title. They need reinforcements in their starting rotation, and a 2-3 year deal with May could be the perfect move. It's not difficult to see the flashes of potential when May pitches, and as a result, the 29-year-old right-hander will likely bring in a decent contract this offseason.

RHP Antonio Senzatela: Los Angeles Angels

There is certainly an argument to be made for Milwaukee to try to retain Antonio Senzatela after declining his mutual option last week. Since converting from a starting pitcher to a reliever, Senzatela has shown an ability to be an effective high-leverage bullpen option. Despite some inconsistency during the final weeks of the regular season, Senzatela impressed in the postseason -- he appeared in four games, scattered three hits, and allowed zero earned runs.

However, it's likely the Brewers believe they can replace Senzatela's contributions internally without having to give the soon-to-be 32-year-old right-hander the multi-year contract he's likely to command. The Angels, under new front office leadership and new ownership, need help everywhere, but especially in the bullpen. Landing Senzatela could be a solid move to bolster their bullpen group, and potentially their starting rotation depending on how the versatile right-hander is used.

LHP JoJo Romero: Milwaukee Brewers

Of all their pending free agents, JoJo Romero should be the top priority to bring back for 2027. Romero was excellent for Milwaukee to end the regular season and throughout the postseason. He was the perfect complement for lefties Aaron Ashby and DL Hall, sporting a unique arm slot that kept opposing lineups off-balance.

His performance will certainly warrant plenty of attention from teams with bigger pocketbooks. The St. Louis Cardinals, Romero's former team, is reportedly already interested in a reunion. Other teams who miss out on the Adrian Morejón sweepstakes may turn to Romero as a strong alternative. The Brewers should be slightly more aggressive here than they usually are with free agent relievers, especially if Romero's contract ends up being in the range of two years, $12-13 million.

C Gary Sánchez: New York Yankees

El Kraken back in the Bronx? It certainly makes some sense. The Yankees' starting backstop, Austin Wells, struggled in 2026, hitting for a .186 average and 14 home runs. As a result, the Yankees are in the market for a catcher, and many fans want a high-profile trade acquisition like Shea Langeliers or Hunter Goodman. However, if they can't swing a deal for one of those two, or if they need a veteran back-up to complement them, a reunion with Sánchez makes plenty of sense.

The Brewers have other options at the back-up catcher position that don't require them to give Sánchez another free agent deal. Assuming William Contreras returns as the starting backstop in 2027, both top prospect Jeferson Quero and trade deadline acquisition Bo Naylor could serve as viable back-ups to the iron-man All-Star.

LHP Jared Koenig: Pittsburgh Pirates (minor league deal)

Pittsburgh is looking for bullpen help with hopes of contending in a loaded NL Central. Koenig, who has the upside of a high-leverage southpaw, could be the perfect reclamation project on a minor league deal for the Pirates. It's the type of low-risk, high-reward move the Pirates should be making to fill out their pitching staff.

Koenig was great out of the 'pen for Milwaukee in 2024 and 2025, but injury kept him sidelined for most of 2026. In limited relief work at the big league level, Koenig appeared in just nine games for Milwaukee, working just 7.0 innings and giving up seven earned runs on 12 hits, while also walking seven batters. The Brewers might be interested in bringing Koenig back on a minor league deal and seeing if he can rediscover his prior form, but more likely that's a move another organization will make.

RHP Bryse Wilson: Chicago Cubs (minor league deal)

The Chicago Cubs flat out need to fill innings next year. Seven multi-inning pitchers who were on the Cubs' Wild Card roster -- Shota Imanaga, Kevin Gausman, Clay Holmes, Matthew Boyd, David Peterson, Aaron Civale, and Colin Rea -- have all become free agents in the days following the completion of the 2026 season. The Cubs will not only need to sign a few top-tier starting pitchers just to fill their free agent losses, but they will also need to find creative ways to cheaply fill innings.

The Cubs brought in Wilson to fill innings during the middle of the 2026 campaign, so they clearly like the right-hander. Wilson, who played for Craig Counsell as a member of the Brewers in 2023, didn't find success with the Cubs this year, but his strong showing in Milwaukee during July and August should have teams interested in his services this winter. Whether or not that means a major league deal for the soon-to-be 29-year-old remains to be seen, but there's certainly a chance Wilson lands with the Cubs regardless.

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