Brewers Linked to Sonny Gray; Trade Questions Remain Ahead
Jun 18, 2026 9:00 PM

As the Milwaukee Brewers ready for Brandon Woodruff’s return, rumors swirl around a potential blockbuster for Sonny Gray.

The Milwaukee Brewers already appear to have one of baseball’s strongest rotation foundations, and there is reason to believe more help is arriving soon.

Jacob Misiorowski and Kyle Harrison have emerged as major pieces at the top of the staff, and that group could expand in the near future.

Brandon Woodruff made what may prove to be his final minor-league rehab appearance Tuesday for High-A Wisconsin.

Brewers manager Pat Murphy indicated over the weekend that the expectation was for Woodruff to make one more appearance before potentially returning to the Major League roster.

Related stories

Woodruff completed 5.1 innings Tuesday while allowing three earned runs and striking out six.

Once he officially rejoins the rotation, Milwaukee could have one of the deepest front-end groups in baseball.

Even with that possibility, the Brewers still have reason to explore another addition before the August 3 trade deadline.

Milwaukee has enough prospect depth to pursue meaningful upgrades and has positioned itself as a team worth investing in.

Despite dealing with injuries throughout the season, the Brewers remain 45-26.

For comparison, the Los Angeles Dodgers sit at 48-27 and the Atlanta Braves are 46-27.

Milwaukee has maintained that pace despite currently operating without Woodruff, Quinn Priester, and Logan Henderson.

That naturally raises the question: What if another starter joined the group?

On Wednesday, Jeff Passan and Kiley McDaniel from ESPN released their list of the top 100 trade candidates and identified Boston Red Sox starter Sonny Gray as a possible fit for Milwaukee.

Passan and McDaniel estimated a 25 percent chance of a trade and outlined the complications attached to Gray.

Those include his no-trade clause and the financial commitment remaining on his deal.

Gray would be owed roughly $10 million for the final two months of the season and also carries a 2027 mutual option worth $30 million with a $10 million buyout.

The report noted that mutual options are rarely exercised, creating additional cost concerns unless Boston agreed to absorb salary and Gray approved a move.

“Like with [Willson] Contreras, there are complications. Gray also has a no-trade clause. And then there's the financial matter: On top of the $10 million or so he'd be owed in salary for the final two months -- around the same as Skubal -- Gray's restructured contract after his trade from St. Louis to Boston includes a $10 million buyout on a $30 million mutual option for 2027,” they wrote.

“Considering mutual options don't get picked up, that is a pricey deadline acquisition, leaving Boston somewhat hamstrung unless it's willing to pay down a significant portion and convince Gray to accept a deal.”

Gray’s Value for Contenders

The production side of the discussion is easier to understand.

Gray is 8-1 with a 3.03 ERA, 1.20 WHIP, 51 strikeouts and 16 walks in 62.1 innings over 12 starts.

Milwaukee also has recent history finding success in pitching-related deals with Boston, including acquisitions involving Harrison and Priester.

Gray has additionally shown an ability to thrive in smaller markets during previous stops with the Athletics, Cincinnati Reds, and Minnesota Twins.

Still, the financial structure remains difficult to ignore.

Paying a significant buyout without certainty beyond the season creates legitimate concerns.

Gray may fit Milwaukee’s on-field needs, but the economics may only work if Boston contributes financially.

Beyond results, Gray brings qualities that contenders value.

One of his biggest strengths is composure.

He consistently maintains control of situations and rarely lets moments speed him up.

Another defining trait is adaptability.

Gray has repeatedly adjusted his style and remained effective in changing environments.

He also competes with conviction and carries veteran presence that can influence an entire pitching staff.

Those traits explain why teams continue viewing him as a meaningful rotation addition even as contract questions complicate the conversation.

Join the Community

Don’t miss out on our ROUNDTABLE community and the latest news!

It’s completely free to join. Share your thoughts, engage with our Roundtable writers, and chat with fellow members.

Download the free Roundtable APP, and stay even more connected!

Comments
anonymous profile image
Powered by RoundtableAn AI/DeFi-powered Enterprise Media Operating System. Learn more at Roundtable.io.© Roundtable 2026. By using this site you agree to the Terms of Use and Privacy Policy