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What I'm wondering is ... why NOBODY has ever given a Carlos Lee-type contract to a David DeJesus- or John Jaso-type player.
You and Kite are arguing that MOST current shot-callers are USUALLY idiots.  I'm observing that ALL of them, the young guys like Epstein and the old guys like Gillick, ALWAYS agree on some very important issues.  
The argument that MOST GM's are idiots, the argument that there is a LOT of stupidity, that is totally irrelevant to this entire discussion.  
There have been no exceptions to this syndrome.  Nobody has ever given David DeJesus $100M.  There has never been a Soriano-style bidding war for a "projectable" soft-skills WAR hero who couldn't hit.
EVERY GM IN THE GAME will pay a 110-RBI man -- if they are confident that the man will deliver the 110 RBI.  It's not old-school GM vs young GM, and you can't show me any young GM's who paid a David DeJesus.  It's just a matter of, "Do I think this guy will gimme the RBI?"  
Theo Epstein gave Ortiz the money.  He didn't worry about Manny Ramirez' defense, baserunning, or WAR when he took on that 7-year contract.  He wanted the RBI.
.............
But let's cut to the bottom line.  Are you saying that, if you were GM, you'd give JJ Hardy the same money as Shin-Soo Choo?   You'd give Erick Aybar the same money as Paul Konerko?  Mark Ellis the same money as Billy Butler?
Does that mean you'd give Choo only $5M, or does it mean that you'd give Mark Ellis $17M?