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Hillary Clinton is the last gasp of the boomers

I’m more interested in how “folks wanna pop off” found its way into the President’s lexicon. Does he possess a reservoir of culturally relevant slang terms and colloquialisms that he employs when White people aren’t around? We know he code switches... but he’s also a 54-year-old man who hoops in Sam’s Club Nikes and tucks his shirt into his sweatpants...This is not what cool people do. Cool people do, however, reflexively use “pop off” to address haters. President Obama is a paradox. - Damon Young
On the topic: we aren't ever going to see anything like this written about Hillary Clinton, are we? For every (probably choreographed) media moment where Obama drops a reference from urbandictionary dot com, we have - particularly in recent months - seen an (equally choreographed) grasp at relevance from Clinton. But Hillary is about as connected to youth culture as Homer is when he tries to talk to the kids about Grand Funk Railroad. And the only people who would deny this are other olds.

Take for example what was clearly orchestrated as a meme-worthy moment of casual Clinton hipness:

This of course got precisely the reaction it was begging for...

...from people in their fourties.

It can't be exaggerated just how dated and derivative this is. Clinton remembers it because Obama did it to her almost eight years ago, and even then the Jay Z reference was already about seven years old. When this was fresh, during Bush's first term, most of Clinton's youngest supporters were already in their thirties.

This is the rule of Clinton-culture: she can only see America's youth through the eyes of a boomer. She brings Katy Perry on board because Katy Perry is one of the few pop stars that 64-year-olds will listen to. She is baffled by emojis and crashed and burned when she tried to use them in her campaign. Her media surrogates are left to praise the hipness of...writing in cursive, black-and-white polaroids from the 1950s, and (seriously) "hold[ing] something up against a brightly colored wall".

To answer Young's question, we can be fairly certain what is actually happening. Barack Obama has a communications team that keeps close tabs on youth culture, and they tactically integrate this into their messaging. As proven in 2008, they are able to do this far more effectively than Clinton. This is in part because the Clintons bring with them a network of aging professionals who have accumulated on their aging political careers like dust on a Fleetwood Mac vinyl.

Paradigm case-in-point, Peter Daou: best known as a proud death squad vet, but also a 50-something media advisor who has built his career around the Clintons. He was the Internet Director for Hillary's disastrous 2008 online campaign; right now he seems to be vying for another position with his hilarious "Hillary Men" initiative. So far, this has mostly involved Daou (and 50-something partner Tom Watson) whining about getting pwned by the kids, rallying the olds, and hilariously failing at social media.

We almost never see these kinds of disasters with Obama because Obama hasn't spend as long building up a stagnating professional entourage. And this is one reason why Bernie Sanders has had a far more successful youth campaign as well. It's not the candidate's age that matters (Sanders is older than Clinton and clearly finds social media baffling as well, though he does appear to have an instinctive knack for it); it's the age of his campaign, which of course reflects his campaign's relationship with the culture. The kids, of course, totally get it:

Hillary Clinton's professional media surrogates don't seem to have picked up on this yet, though they will one way or another. She can't speak to the young because she's surrounded by aging boomer cronies, and if she gets elected we're going to be dealing with boomer culture and boomer politics until the rest of us are as old as they are.