Signing the best free agent pitchers is the most expensive. And in the end, usually the worst way to rebuild a staff. And as you pointed out, none of Pedro, Lowe or Schilling were free agents.
Yes the 2009 Yankees spent heavily and it paid off with a title. But is that really the most common result when the Yankees pay heavily? Like they did in 2001 for Mussina or 2002 for Giambi or 2004 for ARod? And how did Price work out for Boston?
Really look at the biggest deals in Sox history - Price, Manny, AGon, Crawford, and Sale, Manny’s deal (which Epstein appeared to have a prime directive to unload) was the only one that was actually any good. Why do people want to continue pursuing this? If you have a HOF caliber player like Manny, it makes sense. Betts would have made sense. But for anything else, the results aren’t even mixed for this team…