The 2025-26 MLB offseason has been anything but quiet, especially for the St. Louis Cardinals and Boston Red Sox, who have set the hot stove ablaze with a flurry of trades that’s left fans and analysts buzzing. Since the 2025 trade deadline, the Cardinals have made four trades with the Red Sox—a remarkable run of deals that’s drawn attention not just for its frequency, but for the intriguing connections between the two clubs’ front offices.
At the center of this transactional whirlwind is Chaim Bloom, a name familiar to both fanbases. Bloom, who was hired by the Red Sox prior to the 2020 season as their Chief Baseball Officer at just 36 years old, spent four years in Boston with a mandate to lower payroll while keeping the team competitive. His analytical approach and eye for talent were lauded, though his tenure was not without its challenges. After leaving Boston, Bloom joined the Cardinals as an advisor to then-president of baseball operations John Mozeliak, with many expecting he’d eventually take the reins himself. That expectation became reality after the 2025 season, when Bloom was officially named president of baseball operations in St. Louis.
Since stepping into the top job, Bloom has wasted no time putting his stamp on the Cardinals. In just two months of the offseason, he’s orchestrated three major transactions involving his former team. The Cardinals traded starting pitcher Sonny Gray and first baseman Willson Contreras to the Red Sox, and signed free-agent starter Dustin May—who, in a twist of fate, had just finished the 2025 season pitching for Boston. If you’re counting, that’s three significant moves, all involving the Red Sox, and all setting the stage for what could be a transformative year for both franchises.
But the trade activity between these clubs actually kicked off at the 2025 trade deadline, when the Cardinals sent swingman Steven Matz to Boston in exchange for first baseman Blaze Jordan. At the time, Bloom was still serving as an advisor, helping Mozeliak navigate the market. Since then, the pipeline has only grown busier. Over the last six months, the Cardinals have acquired seven players from the Red Sox: Blaze Jordan, Hunter Dobbins, Dustin May, Brandon Clarke, Richard Fitts, Yhoiker Fajardo, and Blake Aita. That’s a veritable Boston-to-St. Louis express!
Some fans have raised eyebrows at the frequency of these trades, wondering if Bloom’s connections to his old team are influencing the Cardinals’ strategy. But a closer look suggests these deals are more about fit than familiarity. Only two of the seven players acquired—Blaze Jordan and Hunter Dobbins—were actually drafted during Bloom’s tenure in Boston, in the 2020 and 2021 drafts respectively. The others, including May, Clarke, Fitts, Fajardo, and Aita, joined the Red Sox after Bloom had moved on. As one observer noted, "Bloom's trades with Boston are driven by team fit and needs, not favoritism."
The logic behind the moves is clear: the Red Sox entered the offseason in need of a starting pitcher and a first baseman, while the Cardinals had assets to spare. Meanwhile, St. Louis is focused on the future, eyeing a rebuild that leans heavily on young, controllable talent. Boston’s deep and talented farm system made them a logical trade partner, and the two clubs have found common ground on multiple occasions. Still, the sheer volume of trades has prompted some in St. Louis to joke, "Can Chaim Bloom make any trades with another team?"
So, who are the new faces in the Cardinals’ system? Among the most notable is left-handed pitcher Brandon Clarke, who was just outside the Red Sox’s top 10 prospects but now ranks sixth for St. Louis. Clarke’s raw stuff is tantalizing, with a fastball that can dominate, but his strike-throwing remains a work in progress. He was off to a great start in 2025 before a blister forced him to the sidelines. If he returns healthy and recaptures his early-season form, he could quickly rise up the ranks.
Another intriguing addition is right-hander Yhoiker Fajardo, who broke out in 2025 with increased fastball velocity, now sitting in the low-to-mid-90s and topping out at 97 mph. Fajardo’s changeup and slider both show above-average potential, and he’s shown a knack for throwing strikes despite his youth. He projects as a potential back-end starter and now ranks ninth in the Cardinals’ system.
The Cardinals also picked up right-hander Blake Aita, another promising arm, and free-agent starter Dustin May, who brings experience and upside after a stint in Boston. With these moves, St. Louis is clearly betting on pitching depth and upside as they retool for the future.
Meanwhile, the Red Sox have been anything but passive. In addition to their trades with the Cardinals, Boston has been active elsewhere, making a prospect challenge trade with the Nationals and sending two prospects to the Pittsburgh Pirates in exchange for Johan Oviedo and two additional prospects. The Red Sox’s acquisition of Willson Contreras gives them a proven bat and veteran presence behind the plate, while their other moves have helped replenish the farm system with high-upside talent.
Across the league, the AL East has been the epicenter of trade activity this winter. The Tampa Bay Rays have also been busy, dealing away Shane Baz to the Orioles for a quartet of prospects and participating in a three-team trade that shipped out Brandon Lowe, Mason Montgomery, and Jake Mangum. As of December 24, 2025, a staggering 42 prospects have been traded since the end of the season, with the majority of the top names landing in the AL East. Of the top 13 prospects moved so far, only Harry Ford was not traded to or from an AL East club.
Looking ahead, the Cardinals’ trade activity may not be over. Nolan Arenado, JoJo Romero, and Brendan Donovan remain on the roster, and speculation is swirling that Bloom could dip back into Boston’s farm system or look elsewhere for deals. The question on everyone’s mind: Will the Cardinals continue their Boston connection, or is it time for Bloom to expand his trading horizons?
For now, both the Cardinals and Red Sox have positioned themselves for intriguing 2026 campaigns, with revamped rosters and a new generation of talent ready to make its mark. As the trade market continues to sizzle, fans can only wait and see which domino falls next.
