What Went Wrong? How Hillary Lost

June 3, 2008— -- Back when Sen. Hillary Clinton was just starting her campaign, top aides and advisers had a ready answer when asked if she could win the presidency.

"She's already winning," came the response, as repeated by chief strategist Mark Penn, campaign chairman Terry McAuliffe and other top aides and advisers, in memos, press releases and interviews as the campaign began more than a year ago.

It was a rejoinder that fit the "inevitable" candidate — and for a long while, the response fit the facts.

Clinton, D-N.Y., occupied the race's top perch virtually until the voting started, with a campaign that was designed to hover above the opposition and break through with dramatic early victories that would end the campaign cleanly and quickly.

But her campaign, it would turn out, was based on a series of fundamental miscalculations — about the mood of the electorate, the threat posed by Sen. Barack Obama and even the basic rules of the Democratic primary process.

In retrospect, the mistakes started with a faulty assumption: That inevitability itself could underpin the rationale for a presidential candidacy, even in the face of a deep Democratic desire for change and the wide enthusiasm that greeted a first-term senator from Illinois.

When the veneer of invincibility slipped away, so did much of the campaign's strategic foundations, leading to the staff infighting, public eruptions, financial woes and a string of devastating defeats that contributed to Obama's clinching of the Democratic nomination on Tuesday.

Some strategists maintain that Obama, D-Ill., would have beaten any opponent — that he was the man who matched the moment, with a savvy campaign staff that simply played the game better than anyone else.

But here are five mistakes that Democratic strategists and Clinton campaign insiders say contributed to Clinton's downfall — and left Obama as the last candidate standing in the most remarkable primary season in memory:

1. INEVITABILITY AS STRATEGY

Armed with the best brand name in a generation of Democratic politics, Clinton and her aides could afford to be glib early on: She had the wide edge in polls and had the party's top strategists and money folks locked down early — a signal, she hoped, that her candidacy could not be stopped.

Clinton called her campaign a "conversation," yet it was really always more of a machine: The accumulated muscle of the Democratic Party was powering a formidable messaging and fundraising operation on behalf of a skilled, determined candidate — all helping deliver the message that Democrats had better fall in line or get out of the way.

Yet for all the sharp minds that populated Camp Clinton, the campaign failed to account for the broad and deep desire for wholesale change among Democrats; it was, it would turn out, a particularly bad year to run as a de facto incumbent.

"You did not necessarily have a message that was consistent with what people were looking for in a 'change' election," said Chris Lehane, a Democratic strategist who supported Clinton's presidential bid. "It was inherently limiting — and, as the first female presidential candidate, she could have been the candidate of 'change.'"

The campaign struggled constantly with messaging, through a fitful series of attempts to reach different segments of the Democratic Party. She would emphasize her toughness, then her human side.