It's been a rebuild 2-3 years. I won't use the "C" word for fear of setting off some sensitive posters.
It's also hard to ignore big extensions, when considering the timing of big FA signings.
Among the top 120 Total Contract Value Signings in MLB history, the Sox have 8.
These 8 players were signed under Henry's watch:
19. Price '16-'22
43. AGon '12-'20
47. Sale '20-'24
51. Crawford '11-'17
76. Bogey '20-'25
86. Pedey '14-'21
86. JDM '18-'22
107. Pablito '15-'19
(Other big ones include Dice-K, Rusney, HRam, JD Drew, Beckett, paying Renteria about $40M for 1 year and the cost of Moncada.)
Henry does have a history of stepping back from spending big and then wham, he jumps back in big time. It's interesting to note that out of these top 8 contracts, two began in 2020 (not that long ago), and 7 of them srated after or ran up to 2019 or beyond.
I remember people thinking the winter before 2013 was too much bargain hunting and not enough big splash moves, and that worked out okay.