Hillary Clinton's play-it-safe paradox

Hillary Clinton
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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."

If she tries to break out of the safe mode she is not being true to herself. Trump is nuts, but he is genuinely nuts. He can't run the risk of being disingenuously safe. She can't run the risk of being disingenuously crazy.
Phil Singer
deputy communications manager, Clinton campaign, 2008

But that only went so far.

Though the Clinton campaign has made some modest steps at openness, the narrative rightly persists — fortified by the FBI investigation into Clinton's use of a private email server while at the State Department.

That aside, Trump alone has entirely changed the parameters by which spontaneous, unpremeditated and risky politics is judged.

Therefore, Clinton finds herself in an ironic place: If she behaves any way other than that of an "establishment" politician, she'll be seen as being "political."

Singer is of the mind that Clinton is simply not the person to try to chase that ball that Trump's style tosses her way.

"If she tries to break out of the safe mode, she is not being true to herself," he said. "Trump is nuts, but he is genuinely nuts. He can't run the risk of being disingenuously safe. She can't run the risk of being disingenuously crazy." (Both the Clinton and Trump campaigns did not respond to requests to comment for this story.)

However, not everyone who emerged from the 2008 Clinton bunker thinks the same.

Mo Elleithee, who served as a senior spokesman for Hillary Clinton eight years ago, argues that if she can't beat the "play-it-safe" meme this time around, Clinton will face a perilously similar fate, particularly against an opponent like Trump.

"Too often campaigns look to … minimize opportunities to be taken off message," said Elleithee, who now runs Georgetown University's Institute of Politics. "They want to minimize risk — sometimes to the point that they miss opportunities, because they just play it safe. That is what I think of when I think of 'playing it safe.'"

Elleithee cautions that the campaign shouldn't be too content to let Trump dominate news cycles, even if he's dominating it, as in the past week, with the stuff of political hara-kiri.

"It is still boxing out her message," Elleithee said. "She has a positive message, but it is harder to win if your entire message is: the other guy sucks. She has to make the case for herself."

Clinton's most obvious philosophical challenge of the campaign, going forward, is to not only decide tactically what risks she's willing to accept in prosecuting the message wars, but to redefine her safeness as an asset.

Four years ago, Bill Clinton came to Obama's rescue, delivering a turning-point speech at the Democratic National Convention that put the nation's slow-improving economy into a favorable context for incumbency. Obama is best positioned to serve as Hillary's Bill on the safe scorecard.

"Certainly, they got portrayed as an establishment candidacy at a time [in 2008], when people wanted change," said Ben LaBolt, Obama's 2008 campaign spokesman. "Over half of the country approves of Barack Obama right now — they want to see further improvement in the economy, but those numbers don't expect massive change."

Clinton's crowd-pleasing foreign policy speech last week, which attacked Trump as mentally unfit for the nuclear codes, among other things, was her most aggressive step in this direction. Judged by the flattering media response, and by dispatches from the trail, the speech prevailed.

And yet, Elleithee argues, there are only so many of these kind of Trump-focused attacks Clinton can do before they necessarily default into "playing it safe."

Perhaps emboldened by the good publicity, Clinton's campaign even tried to edit the play-it-safe screenplay of the last year: In an interview on CNN, campaign press secretary Brian Fallon argued that the candidate was "oftentimes" conducting 20 minute, impromptu media avails with her traveling press corps. This was quickly invalidated by reporter's tweet.


On Monday, Trump piled on, criticizing Clinton for not having held a news conference in seven months.

The double paradox for Clinton, is that since she has cultivated such a reputation for conventional and calculated politics, any move deemed to be outside the familiar zone would risk arousing charges of political expedience.

"If she is too out of the box, it might even undermine her ability to be credible," said Singer. "And for better or for worse, one of the negative critiques of Hillary is that she maneuvers and that there is a certain lack of authenticity, and when you do things that are 'out of character,' they are vulnerable to being spun as an example of that."