On Dec. 10, 2025, I wrote about how I felt that new St. Louis Cardinals front office leader Chaim Bloom could learn from his previous tenure in the same role with the Boston Red Sox.

A month later, I want to focus in one aspect of what I said then:

When the time comes, he can't be risk-averse. The other knock on Bloom in Boston was that he felt he had to not only "win," every deal, he had to win in a landslide. And that thought process made him not want to pull the trigger on deals. When the Cardinals are ready to compete again, he needs to be ready to take some chances. And he also needs to take some chances at the trade deadline, something he was repeatedly panned for not doing. And when it comes to trading away players this winter, he can't hold out for the "perfect" deal all the time.

So where are we at?

On one hand, Bloom has been aggressive in trading away Sonny Gray and Willson Contreras. He's clearly shown a willingness to move players, and he obviously feels good about the returns.

On the other hand, is it somewhat troublesome that both of those deals have been with the same team? The same team that he used to work for and has an inherent knowledge of the farm system of? Maybe.

He didn't draft or sign each player that he received from the Red Sox, so it's not like he's only bringing in players he has a history with, but still, his knowledge of the system as a whole may have helped influence him. Until he makes a deal with another franchise, I don't think he's likely to shed his label as being too conservative in his deal making.

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And how about with Brendan Donovan?

Ken Rosenthal of The Athletic wrote the following about the Cardinals and Donovan on Wednesday:

Why have the Cardinals not yet traded Donovan, the player who can bring them the most in a deal? It comes down to a difference in perceived value. The Cardinals view Donovan as a star player while not all clubs see him that way, according to people briefed on the conversations.

Back to the original question

On one hand, Bloom has every right to hold out on a Donovan trade. He's under team control for two years and there's no rule that says he has to trade him now. He could trade Donovan at the trade deadline, next offseason, or next trade deadline. He doesn't need to have the urgency and can sit and wait for the right deal.

On the other side of things, the Cardinals aren't going to compete in 2026 and they probably won't compete in 2027. If the team is not going to extend him into its next competitive window, then is Bloom just playing unnecessary hard ball? Is he back to his old tricks of not wanting to make a deal unless it's the perfect one?

As I stated above: I think Bloom has shown a willingness to make moves, which is good, but until he deals with someone other than the Red Sox, I think the old perceptions and questions will continue to exist.

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