Where Could Brandon Woodruff Land This Offseason? Two Perfect Fits for the Star Pitcher

The two-time All-Star will have an interesting market.

Brandon Woodruff throws some pitches before the Tuesday Milwaukee Brewers National League Wild Card playoff series at American Family Field in Milwaukee on Monday, Sept. 30, 2024. - Mike De Sisti / Milwaukee Journal Sentinel | Mike De Sisti / Milwaukee Journal Sentinel / USA TODAY NETWORK via Imagn Images

The 2025 World Series is nearly in the books, which means the 2025–26 MLB offseason is right around the corner. Just six days after the Fall Classic wraps up, MLB free agents will officially be eligible to sign with new teams — and one of the biggest names available will be starting pitcher Brandon Woodruff.

Despite battling injuries in recent years, Woodruff reminded everyone why he’s considered one of baseball’s most reliable arms. The Milwaukee Brewers right-hander put together an impressive campaign, posting a 7–2 record with a 3.20 ERA over 12 starts.

Here are two potential landing spots that make perfect sense for the veteran right-hander.

Boston Red Sox: Adding Firepower to a Team on the Rise

Sep 30, 2025; Bronx, New York, USA; Boston Red Sox pitcher Garrett Crochet (35) looks back at first base after getting New York Yankees third base Amed Rosario (14) to ground out during the seventh inning during game one of the Wildcard round for the 2025 MLB playoffs at Yankee Stadium. Mandatory Credit: Brad Penner-Imagn Images | Brad Penner-Imagn Images

The Boston Red Sox are coming off a bounce-back season, winning 89 games and snagging the third American League Wild Card before bowing out to the New York Yankees in the first round. With a talented core and a “win-now” mentality, Boston looks poised to be aggressive this offseason — and pitching help is at the top of the list.

With Lucas Giolito and Dustin May entering free agency, the rotation behind Garrett Crochet needs stability. That’s where Woodruff could make a huge impact. While his injury history may limit long-term offers, the Red Sox have the financial flexibility to offer a shorter-term deal with opt-outs, giving Woodruff a chance to prove he’s fully healthy while helping Boston chase another postseason run.

Even as the Red Sox look to re-sign Alex Bregman and fortify their lineup, upgrading the rotation with a proven arm like Woodruff could be a move that pushes them deeper into October in 2026.

Detroit Tigers: Building Around Tarik Skubal for a Stronger Rotation

Tigers pitcher Tarik Skubal throws against Mariners during the first inning of ALDS Game 5 at T-Mobile Park in Seattle on Friday, Oct. 10, 2025. | Junfu Han / USA TODAY NETWORK via Imagn Images

The Detroit Tigers are a team on the rise and fresh off another postseason appearance. But if they want to take the next step — and make a deep run in 2026 — they’ll need to strengthen their rotation behind Cy Young favorite Tarik Skubal.

Rather than trading their ace, Detroit should look to add another frontline starter, and Woodruff fits the bill perfectly. The Tigers aren’t known for handing out mega-deals in free agency, but a short-term, incentive-based contract (similar to what they gave Jack Flaherty last winter) could make sense for both sides.

Woodruff’s postseason experience and leadership could give Detroit’s young staff a veteran boost, while pairing him with Skubal would give the Tigers one of the most dangerous one-two punches in the AL Central.

With their competitive window wide open, this is the moment for the Tigers to go all-in — and Woodruff could be the missing piece that helps them seize control of the division.

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