No Extension Talks Between Sonny Gray and Red Sox Should Come As No Surprise

No Extension Talks Between Sonny Gray and Red Sox Should Come As No SurpriseStory byTom CarrollSun, November 30, 2025 at 6:43 AM UTC·2 min read

On Saturday, The Boston Globe’s Alex Speier reported that the Red Sox and Sonny Gray have not discussed contract extensions, even though Boston traded for the 36-year-old on Tuesday in exchange for Richard Fitts and No. 5 prospect Brandon Clarke.

Gray, a three-time All-Star, waived his no-trade clause to allow the deal to go through, seemingly sending a signal that the righty would be willing to call Boston his new baseball home for the next few years - seemingly to finish his career, given his age.

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But with the Cardinals assuming $20 million of his $11 million owed in 2026 and Speier's recent report, this suggests Boston's approach is a cautious evaluation period for Gray before making a long-term commitment.

Though not identical, Boston faced a similar situation with Lucas Giolito, age 31.

Debuting for Boston in 2025 after rehabbing UCL surgery in 2024, Giolito became their true No. 2 starter.

Across 26 starts, the righty was 10-4 with a 3.41 ERA, striking out 121 batters in 145 innings pitched. He had a WHIP of 1.290 and a WAR of 2.1.

Sep 17, 2025; Boston, Massachusetts, USA; Boston Red Sox starting pitcher Lucas Giolito (54) pitches against the Athletics during the first inning at Fenway Park. (Eric Canha/Imagn Images)

To say Giolito exceeded expectations would be an understatement. That type of stat line from a guy whom many in the media had written off as being a washed-up addition by Craig Breslow was integral to the team making the playoffs for the first time since 2021. And with right flexor irritation ending his 2025 before the postseason could even begin, his absence from the rotation was felt in a real way.

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Boston’s pitching depth ran out after Garrett Crochet’s dominant Game 1, and they became the first team in the new playoff format to blow a 1-0 series lead in the three-game Wild Card Round against the Yankees.

Despite his value to Boston being clear as day, the Red Sox opted not to extend a qualifying offer to Giolito, making him a free agent available to any team in baseball.

While the Red Sox had a productive test drive with Giolito, they ultimately felt like giving a semi-big-money deal to a guy with consistent injury problems was not a risk worth taking for a pitcher on the wrong side of 30.

Given that Gray is five years older than Giolito, Boston's lack of extension talks aligns with its consistent strategy of evaluating veteran starters before making offers, regardless of the player's expressed desire to stay.

Jul 8, 2025; St. Louis, Missouri, USA; St. Louis Cardinals starting pitcher Sonny Gray (54) looks on after giving up a one run single to Washington Nationals left fielder James Wood (not pictured) during the third inning at Busch Stadium. (Jeff Curry/Imagn Images)

Let's see what this thing can do after gunning it on the highway in high-heat at over 100mph across 30 starts before we start filling out the form for a vanity plate.

​Tom Carroll is a contributor for Roundtable, with boots-on-the-ground coverage of all things Boston sports. He's a senior digital content producer for WEEI.com, and a native of Lincoln, RI.

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