Criswell's WAR today is 0.0. Giolito's is also 0.0. Sale's is 3.8, and he's the one pitching for the Braves while the Sox pay $17M of his salary. Giolito and Sale were huge misjudgments by Breslow, and Criswell cannot make them go away.
Breslow gets credit for bringing in Bailey as the pitching coach, but has been a disaster in finding and/or keeping good arms.
Yes, I would prefer that JH spend a lot more on players, especially pitchers. On the other hand, there is a wealth of evidence that his CBO's and others in the front office are clueless on how to spend that money intelligently.
Thus do I cite--yet again--the example of David Dombrowski, who has repeatedly demonstrated he knows how to acquire talented players and to produce successful MLB teams--see Miami, Detroit, Boston, and now Philadelphia.
However, I also believe that all came crashing down in 2019 when the Sox, still with DD at the helm, had the biggest payroll in MLB, did not even make the postseason, and were in need of a whole lot more cash to keep Mookie out of the clutches of the wealthier Dodgers. They also needed to continue paying Sale and Price big bucks even though both were done, and to find and pay big bucks for their replacements in the Sox rotation.