Image: Sen. Hillary Clinton
Elise Amendola  /  AP
Sen. Hillary Clinton speaks to the American Israel Public Affairs Committee on Wednesday in Washington.
By Chief White House correspondent and political director
NBC News
updated 6/6/2008 4:29:33 PM ET 2008-06-06T20:29:33

A close friend of Sen. Hillary Clinton argues that “Coulda, shoulda, woulda” ought to be the title of any book written by one of her campaign staffers.

No doubt, it would chronicle what went wrong with the most anticipated presidential candidacy in a generation.

According to this same friend, this phrase is one that Hillary Clinton loves to mutter when folks try to tell her what she did wrong.

Then she tells those folks to look forward.

Not since Ted Kennedy’s 1980 campaign had a presidential candidacy been so hotly anticipated.

Because of that, pinpointing the moments when the "wheels came off the wagon" will likely consume the media for days, weeks, even months.

There will be so many political obituaries that it will be hard to keep up.

Finger pointing
Some obituaries will be filled with finger pointing (mostly at Mark Penn and Bill Clinton); some will focus on the strategic blunders (Iowa and other caucuses); and some will ponder whether she ever really had a chance (her gender and last name).

So instead of simply looking at what Clinton did wrong, I want to delve into the "coulda, shoulda, woulda" of her campaign.

One of the more remarkable things about this campaign was Clinton’s strong finish.

Video: Secret Clinton-Obama meeting Sure she benefited from the fact that Sen. Barack Obama stopped campaigning against her after May 6, but that shouldn't take away from her impressive finish.

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Besides having some states and primaries to herself, why did she still look so formidable in these final weeks?

One word: women.

Clinton should not have avoided being labeled “the woman candidate” for president.

Early on, probably with the advice of Mark Penn and perhaps her husband, Clinton seemed to shy away from trying to create a women's movement. It was similar to the way Obama did his best not to be labeled “the black candidate.”

Instead, Clinton focused on her strengths, showcasing her preparation for a job the country has seen exclusively held by men.

In Obama's case, it was probably smart to force voters to view him as someone above race. It was safe to assume that if he showed an ability to win over whites, blacks would eventually embrace him.

But it was an incorrect assumption, as it turns out, that women would embrace Clinton in a similar fashion.

Perhaps women would eventually gravitate (they did late, and they would have in the general), but the campaign was slow to embrace its own historical significance.

Again thanks to Penn, the campaign framed the launch of her candidacy as Bill Clinton's third term, which in turn pushed the media to cover her more as a Clinton and less as, well, a Hillary.

The launch showcased her 35 years of experience, which immediately centered not on her term as a senator but as a first partner to Bill Clinton in Arkansas and the White House.

This led the media to cover the campaign that was in front of them, rather than the one it was assumed she would run.

Given that women have consistently made up 55 to 60 percent of just about every Democratic primary electorate, it's stunning that she didn't win on the numbers alone.

The candidate who happened to be a woman
But again, Hillary Clinton didn’t run as the woman candidate, she ran as the candidate for president who happened to be a woman.

This may have actually failed to attract women early — those who weren't crazy about Bill’s antics and were therefore less inclined to support his wife.

Early on Hillary Clinton didn't do what Al Gore eventually did so well late in 2000 — and that is make the case that she was her own candidate, separate from Bill's legacy.

Gore made it clear he was his own man when he picked Joe Lieberman – the Senate’s leading morality critic of Bill Clinton – as his running mate.

It is always a challenge for a sitting vice president to try to replace his boss.

But Hillary never had this moment.

Instead the campaign believed "Clinton fatigue" was a media created myth and that Bill Clinton’s tenure in the White House was nothing but an asset for voters.

So she embraced the idea of continuing the Clinton legacy rather than focusing on the historical significance of her campaign to women.

It’s over on Super Tuesday?
On the process front, much of the "shoulda" in these campaign obits will highlight the decision to focus on Super Tuesday as an end date, forgetting that this contest was actually a fight for delegates.

The infamous story, now confirmed many times over, is that Mark Penn didn't know that California wasn't a winner-take-all state. It is the anecdote to end all anecdotes when it comes to the campaign’s excuses for ignoring the caucuses.

But aside from that actual strategic blunder, it is still shocking Clinton was able to attract so little superdelegate support.

To convince only 25 percent of superdelegates to sign on to her inevitable campaign should have been a warning sign early on of the amount of Clinton fatigue inside the party.

There were a number of Democratic activists waiting to move on, they just needed a vehicle. Obama turned out to be that vehicle.

Yet it wasn’t just the lack of superdelegate support that led to her defeat. Clinton may have lost the process fight much earlier.

This was not a friendly primary calendar to Clinton, nor were the rules themselves particularly friendly (see Florida and Michigan).

Clinton may have lost this fight as early as Feb. ’05 with the election of Howard Dean as chairman of the Democratic National Committee.

Dean’s election was a clear break from the past, and from the Clinton way of running the DNC. In hindsight, it was a mistake for a political family which believed it controlled the Democratic Party to have allowed Dean and his grassroots followers to take over.

Perhaps the Clintons believed they couldn’t stop Dean, but this early sign of weakness led to an unfriendly primary calendar. And that included the punishment of Florida and Michigan and the decision to put South Carolina and Nevada before Clinton’s preferred early states of Alabama and Arizona.

While tiny decisions at the time, all resulted in huge ramifications for Clinton’s candidacy.

The '06 factor
One other factor folks may overlook in the Clinton obits is the role of ‘06 Democratic successes in the downfall of the Clintons.

The midterm elections taught many Democratic activists (including those superdelegates) that they didn’t need the Clintons to win elections anymore.

The Democrats won Congress and a majority of governorships without substantial help from the Clintons. Sure the two raised money for the party and for candidates whenever asked, but it wasn’t Clintonistas or Clinton’s Democratic philosophy or ideology that was helping these candidates win.

Video: Chuck Todd’s veepstakes guidelines There was a whole new crew of staff and candidates winning these races.

As for message, consider the fact that Democrats won back Congress in ’06 with a majority of candidates opposing a war Hillary Clinton voted to authorize.

Yet Democrats finding their non-Clinton voice was not the only impediment to the campaign. The biggest stumbling block ended up being one person in particular: House Speaker Nancy Pelosi.

For whatever reason, Clinton and Pelosi have a strained relationship. On the surface it strikes me as Pelosi having a beef with Clinton rather than vice versa.

Maybe there's a reason. Maybe Clinton didn’t pay the expected homage to Speaker Pelosi when the California Democrat took the gavel.

I don’t see this in terms of a rivalry between two strong personalities in the party; both would publicly say there’s room for each of them.

This is something else. And that something else cost Clinton dearly.

From keeping superdelegates from endorsing her, to helping lobby key activists against climbing aboard the Clinton inevitability train, the rise of Nancy Pelosi played a much greater role in the eventual defeat of Clinton than one could have imagined.

Finally, no “coulda, shoulda, woulda” analysis would be complete without addressing Clinton's strained relationship with the media.

The distrust Clinton has for the media dates back to the ’92 campaign. She has simply never liked us.

Campaign bubble
If any of us were the subject of so many investigative and innuendo pieces over the course of a decade, perhaps we’d have the same contempt. However I’d argue her contempt for the press was passed down to her campaign staff leading to a bubble being erected around her camp.

This did nothing to allow Clinton to break out of the controlling, cautious and impersonal stereotype.

Imagine if she launched her campaign with a promise of media access and openness that was akin to what John McCain did. It would have forced Obama to do the same.

One of the under-written stories of this campaign is the lack of access to Obama. But because access to Clinton was even harder to come by, it never became an issue.

Openness to the media might have gone a long way to thaw some of those negative stereotypes.

Clinton supporters may read that last statement and say, “Aha! See, there is your evidence of anti-Clinton bias!”

But it is not bias, it is reality. She can’t expect the media to change its narrative of her if she doesn’t give them an alternative.

By staying inaccessible, by running for Bill Clinton’s third term, by keeping her tax returns and the donors to her husband’s library secret, her actions only fed preconceived notions. It was in her power to change this relationship with the media yet she chose not to.

So a summary of Hillary Clinton’s “coulda, shoulda, wouldas?”

• She shoulda run as a woman from the beginning;

• She shoulda gotten over her disdain for the media;

• She shoulda played the inside game a lot better post '04;

• She shoulda made sure she had more advocates at the DNC;

• She shoulda built a stronger relationship with Nancy Pelosi.

Had she done these "shouldas" she "coulda" been a movement and "woulda" been the Democratic nominee.

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