Con: Things seemed to unravel on him during his time with the Boston Red Sox
It is no secret that things did not end well for Bloom in Boston. While I think many people seem to forget or leave out the fact that Bloom helped the club get to the American League Championship Series in 2021, the Red Sox did finish fifth in the American League East in three of his four seasons running the club.
First, let's acknowledge some context. When Bloom took over going into the 2020 season, the club missed the playoffs the season prior and fired Dave Dombrowski due to the mess the club was in long-term. Most publications at the Red Sox farm system ranked as the worst in all of baseball that year, while the Rays' had been regarded as a top-five system in the game. The Red Sox also had the largest payroll in baseball when they hired Bloom, and that's without an extension for superstar Mookie Betts, who was set to hit free agency after the 2020 season.
Bloom was tasked not only with winning, but also rebuilding the farm system, trading Mookie Betts after ownership decided they did not want to sign him, and figuring out ways to cut payroll while making the club better at the same time. Oh, and he had to do that in a market like Boston that was going to rip him to shreds for decreasing payroll and whatever the Betts trade would end up being.
Frankly, Bloom did not do well in the Betts trade. It's not his fault they had to trade him, and Betts' value was significantly lower with him being in a contract year and everyone knowing Boston was going to move him, but the return package was still not good enough. Plenty of people have almost pointed to Bloom's faults within roster construction, lack of deadline activity, and the free agent deals he did hand out (more on that later). Boston is now a contender in 2024 after the changes Craig Breslow made, so that's not going to look good for his resume either.
To me, a lot of the problems that Bloom had in Boston can be attributed to ownership. If you just go back and look at how the Red Sox have operated over the last 15 years, they seem to change course constantly, and while they've won some World Series doing that, they've also driven out some of the best executives in the game, such as Theo Epstein and the aforementioned Dombrowski.
Bloom ultimately was not a good fit in Boston, but I'll explain more later about why St. Louis may be the cleaner fit.