Brewers, Rays' Biggest Offseason Questions After MLB World Series 2026

The confetti has finally settled on the Milwaukee Brewers' triumph over the Tampa Bay Rays in the 2026 World Series, so now the focus shifts to what's next for both clubs.

Milwaukee earned its first championship in franchise history after a historic regular season. The Brewers won a franchise-record 103 games before putting together an 11-2 playoff record, including eight consecutive wins from Game 4 of the NLDS through Game 3 of the World Series.

Tampa came up short in the Fall Classic for the second time this decade, previously losing in 2020, but the club has won at least 98 games in three of the past six seasons.

The Brewers and Rays are two of the best developmental organizations in MLB. They showcased that ability throughout 2026 en route to meeting in the World Series and both figure to be very good again next year.

Of course, trying to figure out anything for a specific team in MLB right now is difficult because no one knows what sort of labor environment the sport will be in when (if?) the 2027 season arrives.

All that anyone seems sure of right now is there will be a work stoppage of some length when the current CBA expires at 11:59 p.m. ET on Dec. 1.

Keeping that huge caveat in mind, here are the biggest offseason questions specific to the Brewers and Rays as they look to get back to the World Series in 2027.

Do the Brewers Keep This Core Together for Another Run?

The Brewers have been the most successful team in MLB over the past two seasons. Their 200 regular-season wins since the start of 2025 leads all clubs and they have advanced to the NLCS both years, culminating with a World Series title this year.

One big reason for that success is the Brewers kept basically every key contributor during that period. William Contreras, Brice Turang, Jake Bauers, Jackson Chourio, Christian Yelich, Jacob Misiorowski, Trevor Megill, Abner Uribe and Aaron Ashby were all back from 2025.

The only significant departure was Freddy Peralta, who was traded to the New York Mets in January before ending up with the Rays in August.

Even though there are only four impending free agents, not including players with options in their contract, Bauers is the most significant one. He's 31 and coming off a career year that was highlighted by winning NLCS MVP.

In a free-agent class without a lot of high-quality hitters, Bauers stands out because his batted-ball profile is extremely impressive with elite-level exit velocities, hard-hit rates, bat speed, chase rate and walk rate.

The Athletic's Tim Britton projected Bauers for a two-year, $29.5 million contract in August, but his stock has increased significantly since then thanks to the postseason.

A two-year deal might keep Bauers in Milwaukee's price range, but a 31-year-old bat-first player with no track record prior to this season comes with significant risk for any club.

The Peralta trade came as he was entering the final season of his contract. Milwaukee picked up his $8 million team option for 2026 in November 2025, then traded him two months later.

Contreras is in the exact same position with a $15.5 million team option for 2027 before he hits free agency next winter. There's no doubt the Brewers will pick up that option, but their modus operandi is to trade a player who is likely to be priced out of their market a year ahead of time to bring back maximum value.

There would certainly be a huge trade market for Contreras as one of the few high-level defensive catchers who can also hit. He was the only catcher with at least 500 plate appearances in 2026, posting a .270/.341/.417 slash line.

Milwaukee certainly has some flexibility with its lineup this offseason because Jesús Made, the No. 1 overall prospect in MLB, could debut at some point in 2027 after spending the entire season in Double-A as a 19-year-old.

Contreras would be more difficult than Bauers to replace because of positional scarcity.

Jeferson Quero made his MLB debut in 2026, appearing in one game on March 29 before going back to Triple-A for the rest of the year. He's more of a defense-first catcher than an all-around player like Contreras, but the Brewers might be hoping improved offensive output from other players like Cooper Pratt and the addition of Made at some point will make up for the loss of Contreras and Bauers if either or both depart.

What Does the Rays' Pitching Staff Look Like?

If you only look at the Rays' position player contracts for 2027, it would be easy to talk yourself into them being right back atop the AL East because pretty much everyone will be back.

Yandy Diaz might be the big question mark from that group since he is entering the final year of his contract with a $13 million salary and going into his age-35 season, so maybe the front office looks to trade him.

Other than that, though, every other player who was in the starting lineup for Game 5 of the World Series is under contract with no projected salary over $5.4 million.

The pitching staff is where things get really dicey for a Rays team that historically operates with one of the lowest payrolls in MLB every year.

Freddy Peralta seems almost certain to be gone as a free agent after turning his season around following the midseason trade from the Mets to Tampa. Nick Martinez already turned down his $20 million mutual option in favor of a $4 million buyout that allows him to test the market.

Drew Rasmussen hit the incentives in his contract that raised the value of his team option to $20 million .

Ryan Pepiot is someone the Rays might look to count on to make up for the loss in production if Martinez and/or Rasmussen don't return, but he's an unknown quantity after missing all of 2026 due to a hip injury that required surgery.

Shane McClanahan didn't pitch after Sept. 3 due to forearm tightness . He could also be a trade candidate going into the final year of his contract.

In the scenario where Martinez, Peralta, Rasmussen and McClanahan aren't back, that's 522.1 innings from the regular season the Rays would need to replace. Tampa's rotation ranked third in MLB with a 3.51 ERA.

Griffin Jax is also going into his final year of arbitration, so it's not unreasonable to think four of the five Rays pitchers who threw at least 100 innings in 2026 will be pitching elsewhere.

There is no obvious impact arm waiting in the minors to take a rotation spot. Brody Hopkins, their top pitching prospect in MLB.com 's rankings, had a 5.17 ERA in 31 appearances at Triple-A this season.

Even though the Rays have been among the best teams in MLB at developing pitchers, the volume of potential losses to their staff this offseason might make it difficult to repeat as AL East champs and make another deep playoff run in 2027.