The truth is that nobody wins on the big free agent deals except the players. Only a small % of these deals come close to value for the teams.
The Yankees made that huge splash before 2009 with CC, Tex and Burnett. They got a championship out of it so maybe it was worth it. But they ended up getting burned on those deals eventually which is what almost always happens.
The Sox approach has been a disaster the last two years.
There's no easy road to success even for big money teams.