In the movie Moneyball there is a scene near the end in which Billy Beane goes to Boston and Fenway Park to meet with John Henry, who raves about how little the A's paid (in team payroll) for each win in 2022 compared to how much the Yankees paid. He also praises sabermetrics, Bill Henry, whom he hired, and the great job Billy Beane did with the A's that season. Then JH hands Beane an offer to become the highest paid GM in MLB, which Beane later declines.
What we now know is that, while JH liked the notion of low-cost wins, his brain trust, including Theo Epstein, always seemed to be able to make a good case for acquiring excellent players who didn't come cheap. As a result, the Sox under JH not only ended the 86 year drought/curse, but won 3 more WS. Those 4 WS wins are the most by any MLB team, 2003-2023, and pretty strong evidence that John Henry is not as you describe him. Interestingly, three of the WS wins--2004, 2013, and 2018--all happened in part because JH or his brain trust decided to fire the manager and hire a new one. Francona, Farrell, and Cora all won the WS in their first seasons as the Sox manager.
I think what happened in 2019 was the John Henry, having won 4 WS, finally decided to try the route/methodology described in the movie Moneyball. And, while there is some evidence that DD had done something like that with the Florida Marlins, by 2015, when he was hired by JH, he had morphed into a CBO who who had a terrific eye for talent and and no fear in making deals to get it. Thus it was no accident that the 2018 and 2019 Boston Red Sox payrolls were both the highest in MLB.
To give DD his due, he has been been an effective, successful GM/CBO for 36 years and with 5 different teams and is currently doing a heckuva job with the Phillies. He won one WS with the Marlins in 1997 and one with the Sox in 2018. He led Detroit to the 2006 WS, which they lost to the Cardinals and the Phillies to the 2022 WS, which they lost to the Astros.
Nevertheless, it's clear JH wants to try a different direction, if only because pitchers especially are a huge gamble whose salaries are always guaranteed but never their performance. On the other hand, the Sox pitchers with the three best WAR's right now--Houck (3.4), Crawford (1.6), and Bernardino (1.6)--are all paid the minimum MLB salary.