The Washington PostDemocracy Dies in Darkness

Jon Stewart perfectly diagnosed the problem with Hillary Clinton’s candidacy

Hillary Clinton reacts to host Jon Stewart during a taping of "The Daily Show" in July 2014. (Frank Franklin II/AP)
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Let's stipulate this: Hillary Clinton is going to be the Democratic presidential nominee.

But Clinton's path to that nomination has been far rockier than she or her supporters expected it to be when Bernie Sanders emerged as her main competition. (Don't believe the Clinton spin that they always knew that the 74-year-old democratic socialist from Vermont was going to pose a major threat to her candidacy.)

Some of that rockiness has to do with Sanders, who has emerged as a sort of cause celebre to the liberal left. Even in Sanders's surprising rise, however, are the seeds of Clinton's broader problem in the race: People struggle to relate to her. She often comes across as inauthentic or lacking a basic core of beliefs. The idea of finding out who the "real" Hillary Clinton is seems far-fetched. Even many people who believe she should  be president acknowledge, usually privately, that she is fundamentally unknowable.

In Manchester, N.H. Democratic presidential candidate Hillary Clinton told a young girl she would make it easier for her to run for president (Video: Reuters)

Jon Stewart, the comedian turned late-night talk show host, summed up Clinton's candidate problems very well in a recent podcast interview with Democratic strategist David Axelrod. Here's the key bit:

That's a brutal assessment. But it's not wrong.

Take a look at Magic Johnson, late night host:

Awkward, right? As Stewart said, Magic's inability to pull off the late-night host gig wasn't a judgment against his broader persona — the guy is remarkably successful on and off the court — but simply reflected the fact that not everyone is good at everything. Magic didn't have a feel for what it took to host a late-night show. And there was no amount of coaching or studying that could make it all seem natural.

That's a very good diagnosis of Clinton the candidate, too. She is, without question, someone with long experience in public policy and public service. She has oodles of details about everything she would do if elected president. Her command of issues on a debate stage or in a media interview is without equal.

And yet, when she is out on the campaign trail, the word that most often comes to mind for Clinton is "clunky." Or "formulaic." "Guarded." Inauthentic." "Rehearsed."  You get the idea.  If connecting is the coin of the realm in politics, Clinton doesn't have much money in her pocket.

"Hillary is ... a bright woman without the courage of her convictions, because I don't know what they even are," says Stewart — an assessment I have heard time and again in private conversations with Democratic strategists over the last few years.

While Clinton's closest allies insist she is warm and funny in private, the candidate has never been able to translate those character traits into her public persona. People want Hillary Clinton, but all they ever get is "Hillary Clinton."

That's somewhat understandable, given that Clinton has not only been in the public eye for three decades but has also been the focus of Republican attacks for much of that time. Clinton fundamentally distrusts many of the actors in the political world — including the media — which makes it tough for her to show her true self.

Regardless of the reasons (and how justified they may nor may not be), the Clinton that voters meet tends to be someone who comes across as overly cautious and too political — afraid to say what she thinks about anything for fear of alienating this or that constituency.

In a political environment where a sizable chunk of voters have responded to the blunt realism of Donald Trump, that struggle to connect is a problem. Given Democrats' clear electoral and demographic edges in the 2016 election, Clinton's connectivity issues may not matter. But if her struggles to put away Sanders in the Democratic primary are any indication, then Stewart is really on to something.

Hillary Clinton on the campaign trail

CLEVELAND, OH - On the third day of a bus tour through Pennsylvania and Ohio, Democratic Nominee for President of the United States former Secretary of State Hillary Clinton along with running mate Senator Tim Kaine, and Anne Holton, aboard the campaign bus in Cleveland, Ohio on Sunday July 31, 2016. (Melina Mara/The Washington Post)