Rabbi Frand had a very interesting take on this tonight and linked it to the final curse in the tochaha.
I have done a quick summary below, but he was much more compelling.
R' Frand said the last curse which the Torah mentions in Devarim 28:68 - that the Jews will be brought back to Egypt in a boat and attempted to be sold for slaves, but no one will buy you. Why is this the worst? Because it shows that you are back to square one - back to where you were before you left Egypt. The futility demonstrates that this is the worst of the curses.
R' Frand said that it was not a political statement - but it is ironic what we are seeing right before 9/11. He recalled where he was on 9/11 when he was trying to write his teshuva derasha and he got a call from his son telling him about the plane that flew into the WTC. And then after President Bush stood on the pile of rubble and said -we are going to get you. (And R' Frand remarked that he was enthused - yes - go get them!) Later, there were pictures of people riding on horseback into battle.
But where are we now? The US sunk $2 Trillion into that war and more than 2,400 servicemen and women were killed. But its 20 years later - what do we have to show for it? Without getting into whether we should stay or go, this is a curse that we are back to where we were on that day. And its truly a horrible shame. He wondered - how can someone who lost a loved one fighting in Afghanistan feel right now? Nothing has been accomplished - this is a curse.