As the MLB offseason drags deeper into winter, the Cleveland Guardians are running out of options — and fast. Every passing day narrows the number of realistic pathways for the front office to meaningfully upgrade a roster that still has clear holes, particularly in the lineup. Veterans are signing elsewhere, trade targets are disappearing, and around the league, teams are quietly locking in their plans for 2026.
Cleveland, however, remains at a crossroads.
One of the few organizations still actively reshaping its future is the St. Louis Cardinals, who officially leaned into a transition this month by trading Willson Contreras to the Boston Red Sox. Under president of baseball operations Chaim Bloom, St. Louis is navigating a careful rebuild — selling selectively, reshuffling assets, and evaluating which veterans fit their next competitive window.
In the wake of the Contreras deal — and earlier moves involving Sonny Gray — the Cardinals have made it clear that several established players are available in trade talks. Names like Lars Nootbaar, Nolan Arenado, Alec Burleson, and Brendan Donovan have all surfaced in conversations around the league.
Among that group, Donovan stands out as the cleanest, most logical fit for the Guardians — and perhaps their most impactful remaining opportunity this offseason.
Donovan checks nearly every box Cleveland values. He can hit, he can move around the diamond, and he plays with the kind of discipline and versatility the Guardians’ roster currently lacks. But new comments out of St. Louis suggest that acquiring him may be far more complicated than it first appeared.
On Tuesday, Donovan spoke with multiple reporters on the Cardinals’ beat and revealed a key piece of St. Louis’ offseason strategy: the Cardinals are actively seeking right-handed hitting outfielders, both via trade and free agency.
That revelation matters — a lot.
For Cleveland, it’s bad news. The Guardians currently roster just one right-handed hitting outfielder, and they’re expected to be shopping for the same type of player St. Louis is now prioritizing. That overlap doesn’t eliminate Cleveland from the Donovan sweepstakes, but it significantly weakens their leverage.
In simple terms: the Cardinals want what the Guardians don’t have.
As a result, any Donovan deal would almost certainly require Cleveland to overpay — likely with pitching. Names like Parker Messick or Joey Cantillo immediately come into focus as the type of controllable arms St. Louis would demand to bridge the gap.
That reality makes an already delicate decision even more difficult.
While there hasn’t been fresh reporting connecting Cleveland to Donovan since Jeff Passan labeled him the “best fit” for the Guardians earlier in the offseason, the need hasn’t gone away. If anything, it’s become more glaring.
Donovan would instantly address two of Cleveland’s biggest weaknesses: second base and the outfield. He could serve as a reliable placeholder at second until top prospect Travis Bazzana is ready for his MLB debut, while also providing flexibility in the outfield alongside Chase DeLauter and George Valera. That kind of adaptability is invaluable for a team trying to thread the needle between contending now and developing its next core.
The production backs it up.
Donovan is coming off the first All-Star season of his career, hitting .287 with 10 home runs in 118 games. In 2024, he posted a .278 average with 14 homers and 73 RBIs across 152 games — steady, dependable offense with on-base skills that fit Cleveland’s DNA.
Yet despite those clear needs, the Guardians’ offseason to date has been underwhelming. Their only meaningful lineup moves have been re-signing Austin Hedges to a one-year deal and bringing in Stuart Fairchild on a minor league contract — transactions that do little to move the needle for a team with postseason aspirations.
That’s what makes Donovan so critical.
Landing him would represent a decisive win for Cleveland’s front office — proof that they’re willing to push chips in rather than wait passively for internal development to solve everything. But the cost may be uncomfortable. Without right-handed bats to offer, Cleveland would have to dig into its pitching depth or other valuable assets to get the deal done.
And that’s the tension at the heart of this moment.
The Guardians can play it safe and risk entering 2026 with an incomplete lineup — or they can accept the reality of the market and pay the premium required to land a player who fits them almost perfectly.
Time is shrinking. Options are vanishing. And if Cleveland truly wants to upgrade its roster in a meaningful way this winter, Brendan Donovan may represent their last, best chance — even if the price is higher than they hoped.
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