Brandon Woodruff made his MLB debut in 2017 and has spent his entire career with the Milwaukee Brewers.

The biggest question surrounding the veteran right-hander is whether that relationship will continue in 2027.

A departure would be surprising. Woodruff has reached free agency, but it would be difficult to imagine him pitching for another organization next season after everything he has experienced with Milwaukee.

Woodruff endured an unpredictable 2026 campaign with the Brewers. The two-time All-Star barely pitched during the regular season because of multiple right shoulder injuries, limiting him to only nine starts.

He did not make an appearance during the entire second half. His final regular-season outing came against the Arizona Diamondbacks on July 4, creating significant doubt about whether he would recover in time to earn a place on Milwaukee’s postseason roster.

At that point, appearing in the World Series seemed even less certain.

Woodruff went 2-2 with a 2.98 ERA and 0.84 WHIP in 45.1 innings over nine starts in 2026.

He eventually returned during the World Series and pitched the ninth inning of Milwaukee’s 10-1 victory over the Tampa Bay Rays in Game 3. Woodruff allowed one run on two hits with one strikeout.

Although injuries disrupted another season, Woodruff recovered in time to contribute before the year ended. He now has an entire offseason to prepare for the 2027 campaign rather than attempting to rush through his rehabilitation during the season.

Woodruff’s history with the Brewers should matter during contract discussions. He has been part of the organization for a decade and understands the expectations, coaching staff and environment surrounding the team.

Milwaukee would not be introducing an unfamiliar pitcher into its rotation.

His recovery also demonstrated considerable determination. Woodruff spent months without appearing in a game, faced uncertainty about his postseason availability and still worked his way back onto the World Series roster.

The Brewers should not expect him to immediately carry a full workload or return to his previous peak. They can instead create a role that allows him to rebuild gradually while protecting his shoulder.

Woodruff could also assist Milwaukee’s younger pitchers through the experience he has accumulated. He understands the preparation required to succeed as a starter, the frustration created by injuries and the patience necessary during a long rehabilitation.

That perspective would be valuable even when he is not scheduled to pitch. His familiarity with the organization could help preserve continuity within a staff that has undergone considerable change.

A reunion would carry some physical uncertainty, but both sides already understand the situation. Woodruff knows how Milwaukee operates, and the Brewers know what he can provide when healthy.

After finally reaching the World Series with the only organization he has represented, returning for another season remains the most logical outcome.