Not sure why so many are quick to direct the anger at Henry. The guy has been spending in excess of $200mill each year on our entertainment. Other, more wealthy owners have tried to keep spending in check for whatever reason. Remember Carl Pohlad? He was the former owner of the Twins and was one of the wealthiest people on Earth, but he insisted on keeping the Twins' payroll near the bottom of all MLB teams. And no one knows why. While he was the owner, the Twins became the first MLB team ever to draw 3,000,000 fans in a season. It's not like they weren't popular.
There is no reason a good GM cannot build a good baseball team for less than $200mill. Other GMs do it every year. The Sox just need a GM who can do that, preferably repeatedly.
In fact, I'm not even impressed at all if a GM has to spend $240mill to build a competitive team. I'll take it a step further; it's actually a bad idea to do that, because it all but ensures a period of non-competitive baseball as those expensive contracts start getting older...