I will say, I do think Henry's pattern, if we want to attribute it to him and not his GMs, is to wait until we look close to being highly competitive for a ring, and then spend big on an ace type pitcher via free agency or by trade.
Pedro came before Henry, but the Schilling trade put us over the top and made us a top 2-3 contender.
When things dipped a little, we traded HRam and A Sanchez for Beckett (and salary dump Mike Lowell.)
When things dipped again, we signed Lackey to pair with Lester.
A couple last place finishes led to the Price signing and to some extent the Porcello trade (Cespedes via Lester trade.)
When this did not seem like enough, we traded for Sale before the 2017 season.
I'm not sure Henry has felt like we have been "close enough" to splurge on a top pitcher since 2018, and in all honesty, I do not think we have been an ace away from being a top contender since '18.
Is the idea to build up a supporting cast, and then pounce?
Who knows?