There is a natural inclination in politics to avoid being tarred as a candidate who failed the same way twice. And the consensus lesson, if not the formal epitaph, of Hillary Clinton's 2008 flop — evidenced by countless campaign tomes and a cursory Google search — is that she lost to Barack Obama because she "played it safe" — indeed, too safe.
Having effectively clinched her party's nomination Monday night, and readying to face the most reckless opponent in modern presidential history, Clinton has every reason to do just that: play it safe.
"Candidates always do well when the political context in which they find themselves syncs up with who they are, and what their political demeanor is," said Phil Singer, who served as Clinton's deputy communications director in 2008. "You have a situation where the contrast between the two candidates is risk versus safety, and she embodies that both in the way she conducts herself in office and the way she conducts her campaign."
Then again, having surveyed the flotsam that Donald Trump made of conventional GOP challengers, there's a further inclination to avoid making the mistakes of others.
To that point, Singer said what informed the last Clinton campaign's hostility toward the media was the unchallenged Swift Boat attacks John Kerry endured in 2004. (Although it's fair to say Clinton's standoffishness, to put it charitably, dates back decades.) However, it was that arm's-length posture eight years ago that fed the play-it-safe narrative Clinton hasn't been able to shake ever since.
There was much signaling in the runup to 2016 that Clinton would be freer, more approachable, riskier, even, in her second pursuit of the presidency. Last April, Bill Clinton told Town and Country magazine that his wife would need to run as if she had never "run for anything before and establish her connection with the voters." Her aides promised reporters that she would show more heart, be less aloof — that she had learned the lessons from her 2008 failures. She began the race with a listening tour and a series of voter roundtables in Iowa and New Hampshire, an assurance to wary Democrats that "things would be different."