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3 free agents the Brewers can sign to win another World Series in 2027

The Brewers are going to need to continue adding talent if they're going to defend their title next season.

Chicago Cubs v Boston Red Sox - Game Two | Matt Dirksen/GettyImages

The 2026 season has just ended, and no one knows for sure when the 2027 season will begin. Yet it’s not early to wonder whether the Milwaukee Brewers will back up their first World Series championship with another next year.

The Brewers closed out the World Series by defeating the Tampa Bay Rays 4-1 in Game 5 at Tropicana Field in St. Petersburg. It marked just the Brewers’ second appearance in the Fall Classic as they lost in 1982 to the St. Louis Cardinals in seven games.

So, can the Brewers do it again next year? The Los Angeles Dodgers won back-to-back championships in 2024-25 before the Brewers swept them in this season’s National League Championship Series. Yet the last team before the Dodgers to pull off the feat was the New York Yankees, who won three in a row from 1998-2000.

MLB appears headed for a work stoppage beginning Dec. 2 when the collective bargaining agreement between the owners and players expires. Conditions for a long work stoppage haven’t been this ripe since the 1994-95 strike. The owners say they intend to implement a salary cap beginning next season, an idea the players have vehemently opposed for more than four decades.

Yet let’s set aside a potential season-altering lockout for now and look at how the Brewers could position themselves to defend their title in 2027. They shouldn’t have many holes to fill, with just six players eligible for free agency: right-handers Dustin May and Brandon Woodruff, left-handed reliever JoJo Romero, right-handed reliever Antonio Senzatela, catcher Gary Sanchez, and first baseman Jake Bauers.

Here are three free agents that the Brewers could sign to help their chances of winning it all again next season.

LF Ian Happ

Bauers led the Brewers with 26 home runs in the regular season and was the NLCS MVP. Milwaukee, though, has Andrew Vaughn to step in at first base next season.

However, the Brewers’ offense could use another proven bat for a lineup that ranked second in MLB in runs scored last season but 28th in home runs. Chicago Cubs mainstay Ian Happ would upgrade the projected right-field platoon of Sal Frelick and Luis Lara. The Brewers could play the four-time Gold Glove winner Happ in left and move Jackson Chourio to right.

Happ, 32, hit .218/.326/.412 in 156 games this year but belted 24 home runs. The switch-hitter has hit 20 or more homers in five of the last six seasons, and his career on-base percentage is .341.

Happ would not be cheap to sign but also wouldn’t likely command a huge contract. A three-year, $55 million deal could get it done.

LHP David Peterson

Chicago Cubs starting pitcher David Peterson | IMAGN IMAGES via Reuters Connect

The Brewers could again look down I-94 and poach a second player from the Cubs. Chicago acquired left-hander David Peterson from the New York Mets on June 23 in a trade, and he went 6-2 with a 3.70 ERA in 16 games, starting all but one.

Peterson is a groundball pitcher who could fit well in the Brewers’ rotation as a fourth starter behind presumptive NL Cy Young Award winner Jacob Misiorowski, Logan Henderson, and lefty Robert Gasser. Peterson will likely command a three-year, $39-million contract, but the small-market Brewers could handle it.

LHP Steven Okert

Aaron Ashby had a historic postseason, and DL Hall gives the Brewers a second quality left-handed reliever. However, it wouldn’t hurt to have another effective lefty in the bullpen, and Okert is very good.

The 35-year-old helped the Houston Astros win the American League West this season, posting a 2.13 ERA and 0.872 WHIP in 68 appearances. A one-year contract worth $5.25 million, with a club option for 2028, would likely close the deal.

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