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Brewers' 1st Free Agent Signing This Winter Should Be Obvious

The Milwaukee Brewers should move quickly to get a deal done.

Milwaukee Brewers general manager Matt Arnold is seen before the start of Game 5 of the World Series between the Milwaukee Brewers and the Tampa Bay Rays at Tropicana Field on in St.Petersburg, Florida on Oct. 28, 2026. | USA TODAY Network via Reuters Connect

The Milwaukee Brewers just won the World Series. The way that they have built this roster and continue to do so clearly is the right way. The front office deserves the benefit of the doubt, especially this offseason, but that doesn't mean that they shouldn't be active in free agency this winter.

In fact, the first move the club should make should involve one of their own free agents. If Brandon Woodruff is going to pitch in 2027, there's no reason why it shouldn't be for Milwaukee. Woodruff is one of a handful of free agents from the 2026 Brewers out there for the taking right now.

At this point, players can start to sign deals. We haven't seen anything major get done this offseason so far, but there's no reason to wait with Woodruff. After making just nine starts in the regular season in 2026, it's hard to believe that there will be a lot of lucrative competition for the righty. On Wednesday, we did a breakdown of what it could cost to bring the franchise legend back to town. Spotrac has his projected market value at just over $11.8 million over one year. We made the case for a two-year deal at a slightly lower annual value of $10 million per year. Anything more than that would arguably be too high at this point in his career.

The Brewers Should Move Quickly

Milwaukee Brewers pitcher Brandon Woodruff (53) pitches against the Tampa Bay Rays during the ninth inning during Game 3 of the World Series at Tropicana Field in St. Petersburg, Fla. on Oct 26, 2026. | USA TODAY Network via Reuters Connect

But, still, the Brewers should move quickly with him. In the lead-up to the World Series, you could see how important he is to this franchise as he put the finishing touches on his improbable comeback and ultimately pitched in the World Series. It's almost unfathomable to think about him pitching elsewhere.

If the Brewers move quickly and bring him back to town, it'd make things easier elsewhere as they continue to build up this roster. If they were to get a deal done with Woodruff quickly, they'd know if they need another starter and how much money they have to spend elsewhere.

There's a potential lockout coming in December. Arguably, it would be good to get a deal done beforehand. There's no reason to let Woodruff's stint in free agency linger. It's best for both sides to continue the partnership. Once a lockout begins, there's no way to know when guys will be able to start signing again. Frankly, the Brewers should move quickly and get a deal done with the righty as soon as possible.

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