Championships since purchase by John Henry group: Red Sox 4 Yankees 1
The Red Sox are 8-1 in their last 9 postseason games against the Yankees.
That may have been part of it, but I think the Braves came to the Red Sox as they had been interested in Sale before, and made an offer of a suspect at a position the Red Sox had a need for. Supposedly Bloom had offers for Sale, but wouldn’t agree. Brez wanted Gio, and couldn’t quite afford both, and made the deal.
He was a great owner because he hired a good brain trust and underwrote--with on averaged among the highest payrolls in MLB--their recommendations. And he did that from 2002 through 2019. Plus the 2021 and 2022 payrolls were 6th highest in MLB. Those teams ended the 86 year drought and brought 4 WS titles.
As for trading Betts in 2019, the Sox already had the highest payroll in MLB and did not make the playoffs--with Mookie and a bunch of other presumably great and expensive players.
At the same time--say August 2019--DD had to tell John Henry, "boss, I know we already have the biggest payroll in MLB, but I need a whole bunch more to keep Mookie (the Dodgers want him bad and will big very high). Plus, sad to say, our two very pricey starters, Price and Sale, are out of action. We have to keep paying them tons of money, but we also need to spend a bunch more to get two new reliable starters."