It was 1992, I was 12 years old, and much more interested in politics than my friends in the (heavily republican) neighborhood I lived in.  I remember following the primary campaign somewhat, and then falling in love with Bill Clinton (and his wife).  Hillary was very clearly an independent woman, unlike any first lady we had ever had (except to an extent Eleanor Roosevelt), in her willingness to express her own points of view and shape public policy.   I was young, the Clintons were young, the Clintons were the future, and the dark clouds of the Reagan-Bush era were about to part.

So I remained a big fan of both Clintons throughout the Clinton presidency.   Even though, as a college student at the end of the Clinton presidency, I was disappointed that the Clintons had not been able to more fundamentally change our society, I wrote it off to the corrupt tactics of the Republicans.  When I saw Hillary running for and getting elected to the Senate, I knew that she would likely run for President one day, and I thought it likely that I would vote for her.  

Then I went to law school.  My law school was in conservative San Diego.  It was 2002.  The Bush administration was laying the groundwork for an invasion of Iraq.  I was shocked and horrified by what was going on around me.  I started attending protests regularly, and inviting several of my friends to go as well.   I got into heated debates with my fellow students.   The debates usually went something like this:

Me: I'm not saying that war is wrong in all circumstances, but when we go to war, the President has to make the case, and here the case has certainly not been made...the inspections seem to be working and there is no imminent threat...

Republican classmate:  So you support Saddam Hussein?

Me: [Head exploding]

I remember how frustrating it was at the time to see our societal dialogue in its most debased state, with the media marching almost in lockstep with the Bush administration, and few people in positions of influence bothering to raise speak their minds.    

There were a few notable exceptions.    

One was Al Gore, another hero of mine from my junior high days.

Howard Dean was another exception:

What I want to know, what I want to know, is what in the world so many Democrats are doing supporting the President's unilateral intervention in Iraq?

In the next year, I spent a considerable time trying to help Dean win the primaries.

But there were some voices which I expected to hear at this time, but did not.   One of them was Bill Clinton.   Where was Bill Clinton's forceful critique of the biggest foreign policy blunder of modern times?  It was notably absent.  In fact: it was difficult to discern what exactly Clinton's position was:

"I have repeatedly defended President Bush against the left on Iraq, even though I think he should have waited until the U.N. inspections were over...That's why I supported the Iraq thing. There was a lot of stuff unaccounted for," Clinton said in reference to Iraq and the fact that U.N. weapons inspectors left the country in 1998."

I understand the game of politics sometimes demands it, but his was the wrong time for cautious, ambiguously worded statements.  

To Bill Clinton's credit, however, I recently learned that he was against the Iraq war from the beginning (above statement notwithstanding), and simply didn't have occasion to mention it:

Former president Bill Clinton said on Tuesday that he "opposed Iraq from the beginning,"

Hillary Clinton is not responsible for the actions of her husband, of course, but I held her to a high standard as well, and I expected her to show her leadership and put up some resistance against the march to war.  If anybody was in a position to make a powerful argument, and make it more difficult for proponents of the war to rush the country into a catastrophe, she was that person.    But she voted to authorize President Bush to use force against Iraq.  

And she said she has no regrets:

Hillary Rodham Clinton said she is not sorry she voted for a resolution authorizing President Bush to take military action in Iraq despite the recent problems there but she does regret "the way the president used the authority."

"How could they have been so poorly prepared for the aftermath of the toppling of Saddam Hussein?" the New York Democrat asked Tuesday night on CNN's "Larry King Live."

"I don't understand how they had such an unrealistic view of what was going to happen."

Wait, a minute, let's look at that last thing she said again:

"How could they have been so poorly prepared for the aftermath of the toppling of Saddam Hussein?" the New York Democrat asked Tuesday night on CNN's "Larry King Live."

"I don't understand how they had such an unrealistic view of what was going to happen."

And now let's look at that speech that Al Gore delivered before war began (and weeks before Hillary's fateful Iraq vote):

When you ask the administration about this, what's their intention in the aftermath of a war, Secretary Rumsfeld was asked recently about what our responsibility would be for re-stabilizing Iraq in the aftermath of an invasion, and his answer was, "That's for the Iraqis to come together and decide." On the surface you can understand the logic behind that, and this is not an afterthought. This is based on administration policy. I vividly remember that during one of the campaign debates in 2000, Jim Lehrer asked then-Governor Bush whether or not America, after being involved with military action, should engage in any form of nation building. The answer was, "I don't think so. I think what we need to do is convince people who live in the lands they live in to build the nations. Maybe I'm missing something here. We're going to have kind of a nation-building corps in America? Absolutely not." My point is, this is a Bush doctrine. This is administration policy.

Hillary Clinton demonstrated a complete failure of leadership on the biggest issue of her political life (and quite possibly the biggest issue of all of our lives).  

As the 2008 race began to take shape, I think I knew that I probably wouldn't be supporting Hillary Clinton, but she still had not completely depleted the once enormous reservoir of respect I held for her and her husband.  

In political conversations with friends, some of whom had also once respected Hillary, I found myself defending her, and even still thinking that she could make a decent president.   I kept reminding my friends that even though I wasn't going to support her, the fact that she would be the first woman President would be an incredible thing, and would be a big plus on her balance sheet.  I think at that point, I didn't understand how she got it so wrong on Iraq, but I somehow kind of expected her, however unrealistically, to do something surprising and wonderful to redeem herself.

She never did.  The day it became clear to me that a second President Clinton would not be a good thing for our country was when she said this about 9/11:

"I believe we are safer than we were," Mrs. Clinton said.

Say what Hillary? We are safer now than we were before 9/11? Safer than before we started an unnecessary war in Iraq? Safer than when your husband was President? This for me crystallized everything that is wrong about Hillary.  She did the "politically safe" thing by voting for the Iraq war.   Then such was her political tone deafness and willingness to pander that she made a statement parroting a classic right-wing canard that was 1. factually dead wrong, 2. actually unlikely to gain her political support from any constituency (neocons for Hillary?), and  3. actually undermined the credibility of her own husband's administration.

That was when Hillary lost me.   Since then, it has been steadily downhill:

Using the terror card when her back was to the wall in New Hampshire a la Cheney:

DOVER, N.H. - Facing the prospect of defeat in tomorrow's primary, Hillary Clinton just made her strongest suggestion yet that the next president may face a terrorist attack - and that she would be the best person to handle it.

She pointed out that the day after Gordon Brown took office as the British prime minister, there was a failed attempt at a double bombing in London and Glasgow.

"I don't think it was by accident that Al Qaeda decided to test the new prime minister," she said. "They watch our elections as closely as we do, maybe more closely than some of our fellows citizens do.... Let's not forget you're hiring a president not just to do what a candidate says during the election, you want a president to be there when the chips are down."

Playing to blind nationalism, saying that all children should be compelled to say the pledge of alleigance every day, a la McCarthy

"Anybody who tells you that children cannot stand up and say the pledge of allegiance in school is not telling you the truth," she declared. "You got to understand that. It is absolutely legal and right. And I personally believe every American child should start the day saying the pledge of allegiance. I did, and I believe every child should."

And, perhaps, most shockingly, Clinton and her campaign have demonstrated (at best) a pattern of racial insensitivity.  

Speaking of Iraq by the way, there is another candidate who got it right before the war.  I don't agree with him on everything, but the fact that he was right about this issue means a great deal to me.  And there is another candidate who got it wrong, has admitted as much, and has dramatically changed course.   Either one of these guys would be promising choice for our country.  But not Hillary.  She might win the primary, but she has forever lost me.