Analytics, Sabermetrics, and other silly names typically imply a strategic, resource-maximization methodology designed to game the system's rules -- such as non-linearities and thresholds -- to one's own advantage. It is supposed to be Bloom's area of expertise. However, he has demonstrated that he is very poor at it.
In the past 12 months, Bloom has committed numerous errors that essentially wasted resources in entirely unnecessary ways. Each one independently could be considered fairly minor overall and not likely to significantly impact the team, but together they paint a story of an executive who tries but fails to understand how to play the system and how to maximize his own resources. To wit:
a) Going over the first tax threshold at the trade deadline when they were just one small salary dump away from dipping under. As a result, losing Bogaerts or any other QO free agent will net a less valuable pick, and the team will also suffer other disadvantages (perhaps some are minor, but easily avoidable nonetheless). When you are only a few million away from staving off an entire set of disincentives (including one that has downstream effects in future years, i.e., you will qualify for repeater taxes a year sooner) -- and when you are rostering junk like JBJ, Barnes, a tradeable asset (at the time) in JDM, etc. -- you make the necessary moves to take advantage of the non-linearity in incentives between a payroll just under versus just over the threshold. Even if you think you have a chance to contend, there are ways to clear that extra few million without moving the needle all that much on your contention chances (such as finding a way to dump even just a few million of JBJ's salary, while paying his buyout, by attaching a prospect).
b) Letting Thad Ward and Noah Song get drafted via Rule 5 for nothing, while a bunch of disposable players sit on the 40-man roster (including, if I'm not mistaken, the likes of Brasier, Ort, etc.). It says something that -- despite having nowhere near the top farm system in the league -- the first overall pick and another top pick in the Rule 5 were both from the Sox. In short, somehow, other teams with deeper and better farm systems were able to protect their own Rule 5 eligible prospects better than the Red Sox were, despite Bloom's own emphasis on retaining prospect depth at all costs. (Bloom also declined to move any Rule 5 eligible prospects, other than Groome, at the trade deadline -- despite talk at the time that there could be a 40-man roster crunch coming if they didn't move prospects at the trade deadline).
c) By all accounts, significantly overbidding on Yoshida relative to other offers, to the point where Yoshida accepted their offer on the first day he was eligible to take offers (that gives away that the player's own agent thought it was wise to not wait for other offers). Even if the team is confident he's that good, it seems to suggest they either overreacted to their past failures this offseason by deciding to blow the competition out of the water, or they didn't understand the market at all. Either way, they are wasting resources by bidding against themselves on this offer. (I also feel bad for Yoshida, b/c between the signing coming on the same day as Bogaerts', and being overpaid, the fan expectations might end up being rather too high for no fault of his own).
d) Spending big on relievers as an overreaction to a poor bullpen last year -- relievers, especially aging ones, are one of the less likely investments to pan out, in part also because reliever performance is simply more volatile than any other in baseball. They are also a market where you can often find bargains when the market settles (like Strahm last year) -- so it seems odd to sign two expensive relievers so early. Is Jansen that much better than Robertson, for instance, that Jansen deserves an extra $6m AAV and an extra year on his contract?
e) Not giving a competitive offer to Bogaerts before this season began, essentially choosing to wait until he'd be tempted to listen to other teams' offers. When a star wants to stay and expresses willingness to take a little less, you take advantage of that by giving your strongest offer early, before competition can enter (and before the market goes up due to other market-setting deals). In short, Bloom more or less chose to compete for Bogaerts on the open market by low-balling him before then -- essentially throwing away their chance of retaining a home-grown star on a hometown discount.
All of these suggest that Chaim is not equipped to maximize his own resources in a detailed and nuanced way. Even if his signings (like Yoshida or Jansen) work out, and even if Bogaerts' new deal ages badly, it does not change the fact that he does not seem to know how to play the market or the non-linearities in these systems to the team's advantage -- this is unfortunately a tell-tale sign that he doesn't seem able to understand and utilize analytics effectively, despite whatever the narrative is about his career. We've now seen too many instances to think these are just one-off mistakes.