The Boston Red Sox are in the market for pitching upgrades at the MLB trade deadline, which is only 10 days away. Craig Breslow is expected to operate aggressively as the Red Sox attempt to build on their significant positive momentum following the Rafael Devers trade.

Garrett Crochet is locked in a competitive Cy Young race with Tarik Skubal, but the rest of Boston’s rotation could use a facelift. Brayan Bello and Lucas Giolito are broadly trending in the right direction, but the Red Sox need dependability — both in terms of production and health. Few check those boxes better than Pittsburgh Pirates ace Mitch Keller.

ESPN’s trade deadline rankings currently peg Keller as “50 percent” likely to be traded, with Boston listed among his “best fits.” This sounds like the perfect opportunity for Ben Cherington to do the Red Sox one final favor before his seat gets too hot in Pittsburgh.

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Ben Cherington’s final act as Pirates GM might be trading Mitch Keller to Red Sox

Cherington spent roughly a decade in the Red Sox front office and served as general manager from late 2011 through 2015. He did a solid job in Boston, even if the fruits of his labor were largely exploited by his successor, Dave Dombrowski. The 2018 champions from Boston featured several key players acquired and developed under Cherington.

He has since helmed the front office in Toronto and now Pittsburgh. While Cherington’s bonafides are undeniable, he clearly is not cut out for the Pirates job. It’s virtually impossible to build a winner when the owner, Bob Nutting, so heavily restricts spending, but an inability to develop talent internally and capitalize on value in trades — especially when it comes to the offense — has been Cherington’s undoing. The Pirates already fired Derek Shelton earlier this season. Unless things turn around dramatically, Cherington could be in search of a new gig come 2026.

In the meantime, Cherington will attempt to convert veteran talent into long-term upside at the trade deadline. Keller is under contract through 2028 at ascending values — $16.9 million in 2026, $18.4 million in 2027, $20.4 million in 2028. Keller isn’t the sexiest name available, but his fit in Boston is undeniably strong.

Mitch Keller gives the Red Sox something they desperately lack in rotation

Mitch Keller is enjoying his best season to date at 29 years old. He has a 3.48 ERA and 1.14 WHIP through 20 starts, notching 92 strikeouts in 119.0 innings pitched. While Keller doesn’t blow folks away with velocity or generate a ton of swings-and-misses, he operates with tremendous command. Keller rarely coughs up free bases and he tends to minimize hard contact.

Moreover — and this is what makes him such a strong fit in Boston — Keller is extremely durable. He has 30-plus appearances and at least 29 starts in each of the last three seasons. He has yet to miss a starting date in 2025. Injuries are never predictable, but Keller tends to be available and to give his team length on the mound. For a Red Sox team battered by injuries and still waiting on the likes of Kutter Crawford and Tanner Houck to get healthy, Keller’s steadfastness is an appealing quality.

So, if the Pirates are determined to trade Keller and Cherington is comfortable doing business with his former employer, this feels like a no-brainer.