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Yeah that's a great quote by Jessup, ironically used as a defense in tyrannizing and ultimately killing a weaker person. Personally I prefer Weinberg's assessment of the situation: beating up on a weakling.

You cover a lot of ground. First, the quote, in or out of context makes a point, and I agree: The military is a necessary evil.
Policy is made by the politicians. The questions of who we are defending ourselves against, and whether we are conquering or defending, all political.
I personally believe that we need a strong military, and yes, you do neeed defense from Cuba. Are they keeping you safe? Has the US been attacked since 9/11? You can't be 100% safe, but I believe the military and the current administration are doing a stellar job of national defense.
Sometimes the best defense is a good offense, hence the action in Iraq. There are bad people out there. We can't ignore that. I am fully behind what happened in Iraq for many reasons. I have paid attention to what's going on, and for those against what happened, (as I gather you are), we will just disagree, there is no disuading me on this one.
Finally, you state: Maybe military personell SHOULD start thinking for themselves.
The answer is no. A military unit can't function as a group of individuals. Just can't. That won't work. An individual has the option of serving, or not serving in the military, but once in, it's not a democracy. One must do as you are told, it is a team that requires everyone to not question. Imagine a tank line engaging the enemy, but stopping because individual units had questions about the ethics of the confrontation, and the relative strengths of forces.

Finally, you state: Maybe military personell SHOULD start thinking for themselves. The answer is no.

Remind me again, who did the fighting in the revolutionary war? And who did their thinking for them? Funny that this country was founded by simple, civilian men, who each made their own personal decision to take up arms in defense of their liberty----and that they intended for it to STAY that way.

"Sometimes the best defense is a good offense, hence the action in Iraq. There are bad people out there. We can't ignore that."

Taken to its logical end, of course, this argument would result in seeking out and destroying each and every "bad person" on the face of the earth and American control of the entire world to ensure that no more "good people" become "bad".

I don't care if there are bad people out there. My life is no more worthy than anyone else's. I have no right to rid the earth of every potential attacker in advance. I only have to right to offer resistance when they actually DO attack.