John Henry doesn't want to pay guys market rate.
Best Red Sox player of this generation gone. Can't pay him! Might as well dismantle and blow up the whole team for 5 seasons.
FA additions: Masa was an import that nobody else wanted (probably still overpaid). Story was damaged goods and probably cheaper than expected (probably still overpaid). Bregman was brought in on a high AAV opt out deal (and it really f'd up the org to do so).
They extended Raffy after external pressure. The second they got uncomfy, they jumped ship on the only long term big contract they had.
In order to add a big bat this season, they traded for Contreras rather than go to FA. They couldn't pull the trigger on bringing Bregman back.
They add extensions for younger players as it adds cost controlled certainty for a few years. Private Equity is able to determine roughly how much they'll be able to extract each season. Set that budget. Tighten those belts! Whether it works or not doesn't matter because the seats are going to be filled and Sweet Caroline will be played.
That's the new economic reality. Henry is 3rd in MLB revenue, but doesn't want to spend like the Yankees or Dodgers. Henry makes more and more money every year and spends a smaller % on payroll than they did when they won WS every few years.