Why are Bush and co. so obsessed with how the insurgents in Iraq feel? Because they are weak, and this is the only card they can play--hoping to keep the enemy demoralized so that they will not act in a way that disrupts the neocon scenario.
When you're strong, who cares if your enemy becomes bold? In fact, it can be a good thing in war, since it can encourage your opponent to launch unwise tactical operations. There's nothing like overhyped morale to get one's head blown off. This was implicit in Bush's "Bring it on" bravado. Bush felt strong then, so he wanted Iraqi insurgents to feel emboldened. The sooner they showed their hand, the sooner they'd be defeated.
Crying about "emboldening" the enemy is tantamount to begging for mercy in war. It's one of the surest signs that one is on the losing side.
We should univerally mock the usage of this. It would be nice to have someone confront Lieberman with the question:
Senator, it may seem self-evident to you, but I wonder if for the record you could explain to the American people just what is wrong with "emboldening" the enemy?
Call them on it. Press them on the answer. Don't let them off the hook. If they give a fuzzy answer, press them further. If they admit, "more U.S. soldiers will die," then you say, "Really, you mean our men and women over thre can't handle the insurgents?" Of course they can never go down that particular rhetorical road. It would be political suicide for Lieberman to actually be forced give a coherent answer.
It's not that the question about emboldening doesn't have sound military answers (it does), but rather that those using it probably have no such answer in mind, and that candor and open debate would undermine the neocon cause. They use this word because, like all things they use, they have found that they can get away with it, and it works for the time being. It is one of the words that conservatives have appropriated that allows them to put an instant stopper on the debate, because of the implied emotional connotations, namely the very worst thing in the world is that the enemy might feel good about what they are doing.
Make them answer the question. Put them on the spot. It can do only good.