Yankees can help former Red Sox GM get revenge on Boston with offseason trades

And what do you know?! Chaim Bloom has already made a trade with the team that fired him. He sent former Yankees pitcher Sonny Gray to the Red Sox in a surprising deal that helps Boston replace Lucas Giolito. But New York can still be on the winning end of the St. Louis Cardinals' purge.

If the enemy of your enemy is your friend, the Yankees should be set up for an intimate relationship with the Cardinals president of baseball operations. Bloom was fired by the Red Sox in September 2023 after four years as their chief baseball officer. Now that Bloom has freshly embarked on a new mission with the Cardinals and is holding a fire sale this winter to help expedite St. Louis' rebuild, he and the Yankees are ideal collaborators.

Bloom was hired by the Cards for a reason. He's competent, and perhaps a lot more than that. Many of Bloom's moves while at the helm in Boston look better now than they did in the moment, which has made his firing even more controversial and questionable in hindsight. Trading Mookie Betts stands out as the black sheep of his tenure, but on the other hand, Boston's current franchise centerpiece, Roman Anthony, was drafted by Bloom. Additionally, Bloom either acquired or drafted notable contributors like Trevor Story, Masataka Yoshida, and Nick Sogard.

Chaim Bloom can mess with the Red Sox big-time by going into trade business with the Yankees this offseason

Bloom has been fully transparent in his designs to trade away virtually any/all of the Cardinals' prime-aged or older players this winter, most notably Brendan Donovan, Nolan Arenado, and Gray. This is why MLB.com's Mark Feinsand expects the Cardinals to be the "most active" franchise on the trade market.

Gray and Arenado both have no-trade clauses, but it probably won't matter. Gray communicated that he's wide open to waiving his clause, and he just did. There is growing belief that a similar situation applies to Arenado.

The cream of Bloom's assets is Donovan, of course. The 28-year-old All-Star infielder is coming off the best year of his career and could garner interest from the Yankees, Dodgers, Mets, Phillies, Astros, and others, according to MLB Network's Jon Morosi.

Donovan's lethal lefty bat would play well at Yankee Stadium, and New York would be able to find plenty of everyday opportunities for him by utilizing his and Jazz Chisholm Jr.'s positional flexibility and/or by limiting Ryan McMahon's playing time at third base.

With a bit of buzz emerging recently from Boston linking the Red Sox to Donovan (via MassLive's Sean McAdam), the Yankees might want to attack the Donovan market sooner rather than later.

Then again, would Bloom really be interested in trading his biggest fish to his former employer? Maybe. On one hand, you have to think that a guy as professional and intelligent as Bloom isn't going to let pettiness or past experiences dictate what's best for the Cardinals. If Boston put a wildy superior offer for Donovan on Bloom's desk as compared with the Yankees, the decision wouldn't be difficult (or at least it shouldn't be).

On the other hand, you have to imagine that the competitor in Bloom would love to see the Red Sox not succeed, which opens up a unique door for the Yankees to walk through this offseason. Whether or not Yankees general manager Brian Cashman wants to walk through that door and meet Bloom in the next room is another question entirely.