Some of the Sox biggest contracts have been extensions, so some context is needed when we say the Sox don't spend top dollar. From Devers to AGon to the record setting Pedro extension before JH. Other lessers ones included Porcello, Sale & Crochet. (I've probably left someone out.)
The Sox have also gone large on some IFA signings from Masa to Moncada to Castillo to Dice-K, which often came with significant fees.
The Manny signing was before JH, too, but there has been some other big signings- just maybe not top level, outside of Price. Maybe the Crawford signing could be called top level, but that really is not many a whole lot of mega FA deals under JH: Price & CC.
The next level is...
Story, JD, Pablito, HRam & Bregman.
Still, there has been several peaks of major success along the way. The 7 year drought is wearing on some fans, but there does seem to be an uptick in talent and spending in the last couple years.
The future is in JH's hands. He's not going anywhere, despite the wishes of some.