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The Washington Post blog post/article indicating the Nationals are 'patiently and aggressively' pursuing Fielder also indicates that part of the grist for that mill is the owners meeting with Boras.  It also mentioned Boras meeting with numerous other ownership groups.
If I'm a GM, this tactic of Boras going over the heads of the GM ticks me off.  It is a big-time kick to the man region.  Yes the owner is the owner, he/she/it can do wahtever they see fit with their toy/investment.  Still.  I can't imagine that this sits well with GM's, and I can't imagine them not taking great offense at both Boras and his bosses if this happens in a given negotiation.
I'm surprised, actually, that it seems to be so prevalent, and that it seems to be so tolerated by GM's.  At least I haven't heard boo about GM's annoyed at owners injecting themselves in to baseball discussions that they are (usually) less knowledgable of.