How Will Ex-Red Sox GM Handle Trade Deadline Dilemma With Cardinals?

Chaim Bloom is used to being caught in the middle.

During his last two years as the Boston Red Sox’s chief baseball officer in 2022 and 2023, Bloom entered the MLB Trade Deadline with his team around .500 and on the fringe of playoff contention. In 2022, he opted to buy and sell at the same time, and in 2023 he essentially did nothing.

Neither strategy worked, ultimately costing Bloom his job. The Red Sox crashed and burned after both deadlines, finishing 78-84 and last in the American League East both times.

Now an advisor in the St. Louis Cardinals’ front office, Bloom finds himself in a similar situation this year. With the July 31 deadline only days away, the Cardinals find themselves one game over .500 and 3.5 games out of the third wild card spot in the National League.

What would Chaim Bloom do?

A look back, to look ahead for #cardinals. https://t.co/0KwxhXXyUM

— Derrick Goold (@dgoold) July 28, 2025

It’s a tough spot to be in, with the playoffs still within reach but statistically unlikely. According to FanGraphs’ MLB playoff odds, St. Louis only has a 15.8% chance of making the postseason after losing 15 of its last 22 games.

Based on how Bloom handled his trade deadlines with Boston, he’ll likely advise Cardinals president of baseball operations John Mozeliak to hold or sell. Bloom is already set to replace Mozeliak after the season, so he’ll likely want as much flexibility and as many assets to work with as possible. There’s no need for Mozeliak to go for broke and mortgage the future in an effort to save his job, especially with his team trending in the wrong direction.

Accordingly, expect a relatively quiet trade deadline from St. Louis. Two-time All-Star closer Ryan Helsley will likely be moved before he reaches free agency, while Nolan Arenado and Sonny Gray could be shopped as well.

The Cardinals will likely make some moves around the edges to bring in some prospects, but probably nothing major. Bloom doesn’t have a track record of making big midseason splashes, and that seems unlikely to change this year with St. Louis hovering around .500 and its front office in flux.