2020: What It Will Take to Win

Kate Catherall
6 min readMar 6, 2019

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Democrats say it every cycle, but this time it feels beyond doubt: this will be one of the most important elections in our lifetimes. The possibilities of a failed Democratic nominee are devastating to even consider. The stakes are high. And so weighty is the decision to choose a Democratic nominee who is both what our country needs to heal and what our party needs to win.

Contrary to what many pundits would have you believe, there is no singular winning profile for the candidate who can win in 2020. And there is no singular strategy to appeal to a single demographic that will win this election. This will not be a battle just for white working class voters, or just for suburban women or just for communities of color. The old rules and conventions simply don’t apply. Because we’ve never had an election like this one. Donald Trump is President. The terms of the debate are different. The conversation is different. The math is different.

It’s time for Democrats to embrace a new playbook. But on the left, we tend to over-complicate and over-engineer this stuff. We get lost in all the navel-gazing.

In my view, the pathway to victory comes down to four things:

  1. Authenticity

We’ve used this word so much in the last three years that it’s almost lost its meaning. But it’s probably more important than ever. Americans are sick of people trying to sell them things. We are inundated by marketing in our mailboxes, our inboxes, our news media, our Google searches, our televisions, our streaming services, our social media, our radios, and our smart phones. And marketing has gotten sneaky. Authentic interactions with people we do not know have become tragically rare.

Opening one’s inbox each morning can feel like walking blind into a series of Turing Tests. What’s fake? What’s news? What’s propaganda? Is your smart phone recording your conversations? Is that text from a real person, or is it mass marketing? Do you really have to call that number back to talk through your repayment options on your student loans? What’s real, anymore? Who’s real, anymore?

Like it or not, part of Donald Trump’s appeal to voters is that they believe he means what he says, and says what he thinks. I’m not arguing that we should abandon the advantages afforded us by data science and throw out predictive modeling or micro-targeting. But I am suggesting that — to a certain extent — we need to tamp down the degree to which we treat candidates like products to be sold.

Voters can smell the bullshit, and they’re not interested. We need to have conversations with voters, and appeal to them on a sincere, personal, relational level instead of selling them tired slogans and sending them lame mail with black and white doom-and-gloom images and big red text. People want to let “authenticity” become a buzz word. Don’t let them. It’s everything.

2. A commitment to justice and bridging

This is the hardest and most existential challenge facing Democrats. We want a leader who can lift up and hold firm to progressive values: social, racial, and economic justice, fairness, inclusion, and equity. We also want a leader who can reach across the barriers that divide us, to pop our bubbles and engage those who do not share our values.

And yet year after year, we convince ourselves that those two things are mutually exclusive. They’re not. And we shouldn’t accept a candidate who feels they need to choose one over the other. The trouble is we haven’t seen many candidates do this well, so we don’t know what it looks like. We are limited by our own collective imagination of what is possible.

But then Heather McGhee goes on CSPAN and takes a call from Garry in North Carolina, or Beto O’Rourke explains his support for NFL players who are taking a knee, and our conception of what is possible changes.

We should accept nothing less than a candidate who is willing to stand by their values while genuinely engaging those who would oppose them. If we do not find a leader who is willing to prioritize this, and willing to make mistakes and keep trying, then the pendulum will continue to swing cycle after cycle. And we will continue to leave people behind.

3. Voice

Forward. Onward. For All. For The Future. For Everyone. For Families. For Our Children. For America. For Change. Change We Can Believe In. For People. Stronger America. Stronger Together. Ready to Lead. Country First. Restore Our Future. America First. Make America Great Again.

Have you ever looked up an exhaustive list of campaign slogans from American Presidential campaigns? Boy, have I got a fun activity for you.

Some personal favorites:

“We Polked you in ’44, We shall Pierce you in ‘52”

“Grant us Another Term”

“Blaine, Blaine, James G. Blaine! The continental liar from the state of Maine!”

“To Assure Continued Prosperity”

“A chicken in every pot and a car in every garage”

“Better A Third Termer than a Third Rater”

“Not Just Peanuts”

Is it just me, or have we gotten less creative? And less funny? And more generic? And kinda boring? I’m so sick of careful messaging informed by bad polling and bad science. We keep asking the wrong questions via the wrong channels and drawing the wrong conclusions.

We’re so focused on getting it right that instead of singing a melody people will remember, we’re just making more noise.

Our candidates should call to the best in us. They should inspire us. They should be brave. They should be unabashedly themselves. We’ve had enough of “just like everyone else.” Candidates should embrace what makes them different and unique, while giving voice to the universal truths that go unsaid.

When they sing to us, we should want to sing back like it’s 1985 and we’re in the crowd at Live AID and Freddie Mercury is serving up some call and response. We should accept nothing less. There are almost 330 million people in the United States, but only one of them gets to be President. We want to trust the person we elect to the highest office (more on that in a moment), but they should be exceptional. Some people would call that charisma, but they’d be wrong to do so. It’s not about charisma, though of course that doesn’t hurt. It’s about the kind of leadership that calls to the best in us. We need a leader who moves us, who speaks to us, who will be a signal in the noise.

4. Humanity

This one is a doozy. What does it even mean to bring humanity to a Presidential race? It goes part and parcel with authenticity, but it’s more than that. Bringing humanity to politics means shifting the very culture that inhabits our daily interactions.

It means listening, telling the truth, modeling kindness, treating the people you deem unimportant with as much grace and respect as the VIPs, making and admitting mistakes in public, forgiving in public, drawing boundaries, acknowledging blindspots and biases, and debating with equanimity.

It means exercising discipline and consistency with a message, but starting with what the candidate wants to say instead of what the polls tell them to say. It means inviting and accepting feedback, and engaging with decency.

It means treating staff, donors, supporters, undecided voters, press, and critics with dignity. It means using technology as a tool to meaningfully engage voters, rather than as a mechanism for transactions. It means declining to spam supporters’ inboxes with “The sky is falling” emails, even if churning and burning the email list might raise more money in the long run.

It means saying, “I don’t know.” When was the last time you heard those words from a Presidential candidate?

When people tell me they hate politics, I get it. A lot of times, I hate it too. But I’ve made it my life’s work because I believe we can and must change it. Because politics rules our lives, whether we like it or not.

We have an opportunity in this election to hold our candidates and their campaigns to a higher standard, to believe in the possibility of what we have not yet seen, and to begin to turn this thing around. But we have to strip away the facade, get down to the studs, and boldly focus on the foundations of who we are as Democrats, the stuff that really holds us together.

That’s how we’ll usher in a new generation of leadership. That’s how we’ll change culture. And that’s the only way we’ll win.

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Kate Catherall
Kate Catherall

Written by Kate Catherall

EVP of Political Strategy, Avalanche. Co-founder and Senior Advisor, Arena. Formerly 270 Strategies, Obama ’12 & ’08. Feminist. Organizer. Dog mama.

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