As long as the players are producing, those big contracts are fine. Inevitably, they turn into albatross contracts though. It's hard for any team to eat that kind of money. We are fortunate that Henry is willing to do so.
Regardless of whether the Red Sox can afford it or not, I just don't like that way of building a team.
When I become the first female GM of the Red Sox, I'm going with a mostly home-grown team that's supplemented with short contract, 2nd tier players. I'll build a dynasty. Look out baseball!