Don't really want to go into necromancy on this thread, but wanted to reply to this since you took the time to answer my questions (always much appreciated!):
Starting from the bottom-I also know that you've been a fan long enough to remember the seasons surrounding 87 and 91... specifically 89 to 90, where MacPhail traded away his best pitcher and did nothing of note in FA to help out the horrid infield offense or to replace the recent World Series hero and Cy Young Award winner he dealt away.
I say this not because I think MacPhail was a bad GM (clearly, he was not, and the game will be lucky if he winds up replacing Bud), or because I disagree with his style-but because up until he signed Jack Morris, I can't think of (and some quick research backs this up) a major free agent signing by MacPhail that would qualify as "going out and getting what the team needed." He made trades and various other moves, but it's tough to look at TR's time atop the organization (somewhere around the 2 year anniversary now) and say he's been sitting on his hands when it comes to acquiring the power starting pitching that I think we can universally agree is the major issue facing the roster (Meyer, Stewart, Berrios, to a lesser extent both the college reliever experiment and May). I'm simply not sure that outside of Jack Morris, MacPhail is a particularly good model to use when the complaint is lack of free agent impact.
As far as willingness to pay goes, I think there's another way of looking at it (and I'm sure we'll disagree here, but bear with me. I promise that I understand where your complaint on TR's FA spending is coming from): Terry has, by my napkin math, offered a single pitcher 22% of the payroll on a 5 year deal (Santana was offered 80/5, adding his salary to the 2008 opening day roster would have made it a touch under $73m). Obviously, how applicable extensions are to new FA signings (assuming the 'cap' is still in the $105m range, that would make for a 115/5 deal) is a subjective matter and up for debate. Personally? I think it's a better insight into TR's philosophy than his parsimonious spending under a notably cheap owner in one of modern baseball's worst revenue situations. I'm not looking to change any minds or get into an extended debate over why MacPhail was/is more successful than TR (because I think we're on the same side of that), but I hope you'll consider the point.
Great, and I mean great post!