The Blue Jays should be in the market for starting pitching this winter, even after retaining Shane Bieber, who opted into his deal to return to Toronto.

Behind Bieber, Kevin Gausman, Jose Berrios, and Trey Yesavage, it remains to be seen how the Blue Jays will look to fill out the back of their rotation. Max Scherzer and Chris Bassitt are set to hit free agency, and even while figuring that Berrios should be back in the fold after finishing the year on the IL, the Jays will likely look at signing one free-agent pitcher to a major league deal.

Brandon Woodruff is an interesting name that has dealt with several injuries over the last couple of years, but has flashed elite stuff whenever healthy. Since entering the Brewers rotation full-time in 2019, the 6-foot-4 right-hander has been one of the best starters in the National League. In the five years between 2019-2023, Woodruff’s 2.93 ERA ranked fourth in all of baseball among starting pitchers, behind only Jacob DeGrom, Justin Verlander, and Clayton Kershaw. His best season came in 2021, spinning a 2.56 ERA with a 10.6 K/9 and 2.2 BB/9 across 30 starts, finishing 5th in NL Cy Young voting.

The 32-year-old has also been at his best in the postseason, authoring a 3.18 ERA (1.90 FIP), 0.84 WHIP, 12.7 K/9, 1.4 BB/9 across 28.1 innings from 2018-2021. He has established himself as a big game pitcher who can generate a lot of whiffs while keeping the ball around the strike zone. He predominantly relies on four pitches: a four-seam fastball, sinker, changeup and cutter. He mixes in a curveball and sweeper, which account for just 5% of his total usage.

Shoulder surgery in October of 2023 knocked Woodruff out for the entire 2024 campaign, not returning to the mound until last July. Durability could be a long-term concern, especially considering some of the other injuries that came up this past season.

Things couldn’t have gone much better for Woodruff – when he was toeing the rubber at least – in 2025.

Across 12 starts, he produced a 3.20 ERA and 0.91 WHIP, with a strikeout rate (11.6 K/9) and walk rate (1.9) that would have been career highs had he pitched a full season. Despite his fastball velocity falling to an average of 93.0 mph – compared to above 96.0 before his injury – his pitch mix still yielded fantastic results.

Unfortunately, Woodruff dealt with a couple of other injuries that caused him to miss a few starts and led to him missing the postseason. Ankle tendinitis in May and a bruised right elbow (from a comebacker) in June slowed down his rehab from shoulder surgery and delayed his season debut. In September, he suffered a lat strain that resulted in him being shut down for the season. Despite his excellent stretch in 2025, it remains to be seen what effect the injuries have on his free agent market this winter.

Woodruff has proven to be one of the very best pitchers in the major leagues whenever healthy. However, his medical is the big question mark, especially considering he will be 33 on opening day.

Durability will likely be at least somewhat of a concern moving forward, perhaps meaning that his market will include teams that can afford to have him miss stretches of the season. The Blue Jays could easily fancy themselves as one of those teams, with the potential for a healthy Woodruff come playoff time outweighing the moderately high likelihood that he won’t be able to stay healthy all year. Toronto will also have to deal with the qualifying offer, another factor in the overall risk.

The injuries will likely lead to the former Brewer signing a shorter-term deal, which may be ideal for the Blue Jays. Adding Woodruff to an already excellent rotation would give Toronto one of the best units in all of baseball.

Signing him would likely mean that the team needs to bolster their starting pitching depth to some degree, but the potential reward should drastically outweigh the cost here. This would be a slam dunk signing that could go a long way towards the Blue Jays winning the AL pennant.