Cardinals bullpen trade update, Cardinals have already been busy this offseason, completing two notable trades with the Boston Red Sox that reshaped parts of both rosters. As a result of those moves, right-handed starter Sonny Gray and first baseman Willson Contreras are now set to compete in the American League East. Even with those deals finalized, Cardinals president of baseball operations Chaim Bloom remains active, continuing to explore potential trades involving other valuable pieces on the roster. Among those assets, few carry more intrigue than versatile infielder-outfielder Brendan Donovan.
Recent reporting suggests that Donovan’s name has once again surfaced in conversations between St. Louis and Boston. According to Ken Rosenthal and Will Sammon of The Athletic, the Red Sox have expressed interest in Donovan, and league sources indicate that the two clubs discussed him earlier this offseason. While talks do not guarantee a deal will come together, the mutual interest is noteworthy. In fact, Boston recently emerged as one of the top potential landing spots for Donovan, making this pairing feel far from far-fetched.
The logic behind Boston being such a strong fit is fairly straightforward. Donovan’s skill set aligns well with the Red Sox’s current roster needs. He offers defensive flexibility, a disciplined approach at the plate, and consistent on-base ability—traits that could help stabilize Boston’s lineup while also providing managerial versatility. For a team looking to balance immediate competitiveness with long-term sustainability, Donovan checks several important boxes.
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From the Cardinals’ perspective, the appeal lies in what Boston could reasonably offer in return. St. Louis has made it clear that high-upside starting pitching is a priority as they attempt to retool and reinforce their rotation for the future. The Red Sox happen to possess one of the deeper farm systems in baseball, particularly when it comes to young arms with projectable upside. That alignment of needs makes the two clubs logical trade partners once again.
When surveying Boston’s prospect pool, one pitching name stands out as an ideal, though perhaps unrealistic, target for the Cardinals. This is the type of high-end arm that could instantly become one of St. Louis’s top prospects and potentially anchor a future rotation. However, given his ceiling and organizational value, it’s difficult to imagine Boston being eager to include him in a trade, even for a player as useful as Donovan.
That said, the Red Sox do have another pitching prospect who represents a more practical and attainable option in negotiations. This second arm still carries significant upside and developmental promise, making him an appealing return for the Cardinals bullpen trade update without forcing Boston to part with its most prized asset. Such a compromise could ultimately be the key to getting a Donovan deal across the finish line.
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Whether discussions progress beyond exploratory talks remains uncertain, but the groundwork appears to be there. With a clear positional fit, aligned organizational needs, and recent trade history between the two teams, a Cardinals–Red Sox reunion centered around Brendan Donovan is a scenario worth monitoring closely as the offseason continues.
1 high end trade piece the Cardinals could target from Boston in a Brendan Donovan trade: Payton Tolle
Right now, the Boston Red Sox’s farm system is headlined by left-handed pitcher Payton Tolle, who has quickly established himself as not only the organization’s top prospect, but one of the premier young arms in all of professional baseball. Given his ceiling and the way the Red Sox view his future, it’s extremely difficult to imagine Boston being willing to include Tolle in a trade for Brendan Donovan, or frankly, for almost any player during this offseason.
Tolle’s physical profile alone makes him stand out. At six-foot-six, he offers the kind of downhill plane and leverage that teams covet in modern power pitchers. That size pairs perfectly with what many evaluators believe is one of the most dominant fastballs currently in the minor leagues.
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The pitch jumps out of his hand with late life, overpowering hitters and setting the tone for every at-bat he faces. It’s the type of fastball that can anchor a big-league rotation for years, and that alone makes him incredibly valuable to an organization like Boston that is building toward sustained success.
The Red Sox are expected to assign Tolle to Triple-A to begin the upcoming season, a clear sign that his major league debut may not be far away. If he performs as expected against upper-level competition, it wouldn’t be surprising to see him get a look in Boston’s rotation at some point during the year. Teams are generally reluctant to part with pitchers on the doorstep of the majors, especially ones with frontline potential, and that hesitation is amplified when the pitcher in question throws as hard and as effortlessly as Tolle does.
Beyond the fastball, Tolle’s overall arsenal adds to his appeal. He currently features three additional pitches that grade out as average, giving him multiple weapons to attack hitters. While none of those secondary offerings are considered elite just yet, scouts are optimistic about their long-term development.
His feel for pitching, combined with his athleticism and work ethic, suggests there is real room for growth. Many evaluators believe those pitches could take meaningful steps forward, allowing them to complement his overpowering fastball and turn him into a truly complete starter at the big-league level.
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From a roster-building standpoint, it would make sense for Chaim Bloom to at least explore whether there is any possible path to acquiring a pitcher with Tolle’s upside. A talent like that can reshape an organization’s pitching outlook in a hurry.
However, realism has to factor into the equation. Boston knows exactly what it has in Tolle, and prying him loose would likely require an overwhelming offer—one that the Red Sox probably aren’t interested in entertaining right now.
That said, while Tolle himself feels untouchable, Boston does have other pitching prospects with intriguing upside who may be more attainable in trade discussions. Those arms might not carry the same sky-high ceiling, but they still represent meaningful long-term value. In comparison, Tolle sits firmly in the category of players teams build around, not trade away, making his availability this offseason highly unlikely.
1 realistic trade piece the Cardinals bullpen trade update could target from Boston in a Brendan Donovan trade: Kyson Witherspoon
Selected by the Boston Red Sox with the 15th overall pick in the 2025 MLB Draft, Witherspoon was a bit of a surprise gift for Boston when he slid down the board to their spot. The organization was thrilled with the outcome, viewing his availability as a significant win on draft night. Since then, his stock has only continued to rise, and he currently sits as the fourth-ranked prospect in the Red Sox farm system, a testament to both his raw talent and long-term upside.
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Witherspoon brings an intriguing arsenal to the mound, headlined by a plus fastball that can overpower hitters and a sharp cutter that gives him another weapon to attack the zone. He complements those pitches with an above-average slider that shows real swing-and-miss potential, along with solid, if unspectacular, control. While he isn’t yet considered an elite command artist, his ability to mix pitches effectively allows him to project as a reliable starter at the big-league level. Most evaluators see him as a potential middle-of-the-rotation arm, though there’s optimism that he could become more than that if his secondary offerings continue to improve.
One area that could unlock another level in Witherspoon’s game is the development of his offspeed pitches. If he can refine his changeup or add more consistency to that part of his repertoire, his ceiling could rise noticeably. That’s where a potential move to the St. Louis Cardinals becomes especially intriguing. St. Louis has built a strong reputation for helping pitchers sharpen their changeups and overall pitch mixes, and Witherspoon could benefit greatly from that developmental track record. In that environment, he might tap into more upside than he’s currently showing.
From a timeline perspective, Witherspoon is not viewed as a long-term project. In fact, he’s expected to be knocking on the door of the majors relatively soon. If everything breaks right, a late-2026 MLB debut isn’t out of the question, though a more realistic scenario has him arriving early in the 2027 season.
For a Cardinals team that values pitchers who can contribute sooner rather than later, that timetable would be extremely appealing and aligns well with their competitive window.
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If St. Louis ultimately works out a trade with Boston involving Brendan Donovan, many fans might hope for top prospect Payton Tolle to be the centerpiece of the return. However, it’s far more realistic to expect Witherspoon to headline such a deal.
He fits the Cardinals’ needs, their developmental strengths, and their timeline almost perfectly. In fact, he was recently listed among a small group of pitching prospects around the league identified as ideal trade targets for St. Louis.
All signs point to Witherspoon being a highly logical and attractive option in any potential Red Sox–Cardinals swap, making him a name worth watching closely as trade discussions continue to swirl.
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