Bloom inherited the core of the greatest Red Sox team in franchise history. No fans know exactly what he was told to do with it -- all we know for sure is what Bloom did do, which is strip it down in four years so the only guys left are a brittle overpaid pitcher he can't move, and a still maturing slugger he admittedly "bet on" who could become another Miggy Cabrera or another Pablo Sandoval (but most likely, someone in between).
The moves Bloom has made that we can't judge yet are additions to the farm system. A lot of prospects look promising, but right now it's all speculation.
The moves Bloom has made that we can judge are the additions to the parent club. His strengths are finding some decent role players, like Whitlock (whose best days so far were as a rookie set-up man). At the same time, Bloom's weakness is jamming square pegs into roster holes, relying too much on utility disguised as versatility... resulting in mediocrity.
But no one can say Bloom doesn't spend or sign free agents -- it's all about who he recruits. For every Wacha, it seems like there are a Richards and a Kluber. Luckily for Bloom, when he lets Wacha walk, interns posing as posters try to pretend Kluber is better, and Wacha's a mirage (just like he still must be this season, deluding voters into awarding him NL Pitcher of the Month).
Bloom's big money signings excel in one or two aspects -- Yoshida is a consistent hitter and fundamentally sound; Story is a top athlete, with impact potential of speed and power (albeit with inconsistent contributions so far). Neither can be called complete ballplayers, but both are at least elite role players. Let's hope both stay healthy long enough to help form the next core...