I look at the end of the 2019 season in which the Sox fell 24 games in the standings, still owed about $300mill to three pitchers in Price, Eovaldi and Sale who either had a long history of physical injuries or had plenty of injury troubles just beginning at that time, and the Sox never successfully locked up Mookie. On top of it all, the farm system had nothing in the way of immediate help. And while the Sox were coming off the most successful run in team history, two of those seasons the team only won 93 games, not exactly a commanding total and more of a statement about the AL East at the time.
If Henry didn’t decide to change direction at that point, he probably because he did it somewhat earlier.
The problem is, he just got too extreme. Tampa North certainly can work, but is better with a built up farm. Or in this case, even a mediocre one. But the issue isn’t that model, it’s how quickly the Sox thought they could implement it. And why they decided to start the “extend our star players” after letting Betts walk. It should have started there…