To me, any trade where you lose a Hall of Famer in his prime (who continues his Cooperstown trajectory in another city) that doesn't replace him with another Hall of Famer, weakens a team. Four years later, the Red Sox finally have two players from the Betts deal in the starting line-up: Verdugo is having a career year, and Wong is pretty good defensively. Still, their combined WAR is .3 more than Mookie... right now.
I won't even call the Benintendi trade a win for Bloom, because personally I wouldn't trade a decent everyday regular for a decent relief pitcher. Something sapped Beni of his power, but he's still a .280 hitter and Gold Glove outfielder. Maybe if Gambrell eventually contributes to the parent club, the scales will legitimately tip to Boston -- just remember, the guy better be an above-average pitcher to make up for all the ghastly Franchy days.
And consider this about why Bloom spends more on hitters rather than high-end pitchers -- entertainment... Any serious fans know that all title teams focus first at the highest point on the diamond -- the hill, smack-dab in the middle of the field. But we, along with every GM, also knows that pitching is the most expensive commodity. Meanwhile, teams can still draw fans in a place like Fenway if they're bopping big flies off the Monstah!