Hillary Clinton's 2016 strategist: We learned about conventional wisdom the hard way

Next week's midterm elections are a type of laboratory for American democracy. It appears that the results will be highly concerning, and perhaps disastrous. Emboldened and propelled by Donald Trump's attempted coup of 2021 — and his impending 2024 campaign — Big Lie supporters and other anti-democracy candidates may win numerous key races across the country.

The belief that elections are fraudulent or fake if Republicans do not win has become an article of faith for the American right and the "conservative" movement. In a blatant effort to delegitimize America's democracy, Republican candidates are openly announcing that they will refuse to accept the midterm results — before most votes have been cast and before any have been counted.

The potential for right-wing political violence is so significant that President Biden felt compelled to address the nation on Wednesday evening about how American democracy, and the literal safety of the American people, are imperiled by "MAGA Republicans" and their supporters. Many voices in the media expressed boredom or exasperation with this message

The Age of Trump has made many of the analytical tools used by pollsters, pundits, journalists and other political professionals increasingly unreliable or useless. Honest observers admit, at least, that we have no certain idea what will unfold after next week's election. The situation is so fluid and confusing that it is reasonable to envision a scenario in which Democrats actually maintain control of the House and the Senate, or a "red wave" in which Republicans win both chambers by a decisive margin.  

How are the American people responding to this democracy crisis? Public opinion polls have repeatedly shown that in the aggregate they care more about "the economy" than about "democracy" — two ambiguous abstractions. Generally speaking, that's good news for Republicans, and is likely to drive forward their revolutionary and reactionary campaign to end American democracy.

In an effort to find some clarity about the upcoming midterms and what the outcome will mean for American democracy, I recently spoke with Joel Benenson, the founder and CEO of the Benenson Strategy Group and one of the world's leading political and corporate strategists. Benenson was a strategist for Barack Obama's victorious 2008 and 2012 presidential campaigns. He was also the chief strategist for Hillary Clinton's ill-fated 2016 campaign.

In our conversation, Benenson explained his view that the most important factor in understanding elections and campaigns is a candidate's ability to relate to the needs, worries, and concerns of the average voter (or to be perceived as doing so). Winning elections, he argues, is about a candidate connecting with voters on the level of shared values and a common narrative. He cautions that too many Democrats have convinced themselves that "working-class" voters do not vote for Democrats because they are deluded about their own "self-interest." That kind of simplification or incomprehension, he says, can be fatal.

Benenson reflects upon his experience with Hillary Clinton's 2016 campaign and on why Trump was able to win that election thanks to a toxic combination of the Clinton campaign's self-inflicted wounds, the failures of the news media and a populist moment of rage against "elites" and "the system."

Democrats are approaching the 2022 midterms, he says, by amplifying the most dangerous and extreme Republican candidates and placing too much emphasis on Donald Trump. He says he is hopeful, however, that the Supreme Court's recent decision to overturn Roe v. Wade will mobilize Democratic voters. Whatever happens next week, he warns, the Republican Party will remain immensely dangerous to the health of American democracy into the indefinite future.

How are you making sense of all the tumult and confusion of the Age of Trump, the democracy crisis, and the midterms? So much of this is unprecedented.

I get asked frequently: Why do people vote against their self-interest? In reality, they're not voting against their self-interest. They're just defining their self-interest on different terms than you think they should be. If you ask a working-class person, "Why aren't you voting for Democrats? They're the ones who are standing up for working class people," the premise may be true but in the end you have to talk to voters in a way that resonates with them. There are things that these white working-class voters don't like about Democrats, however unfair that judgment may be. Too much of the conventional wisdom about campaigns and elections is focused on approval ratings, the economy, the unemployment rate, and metrics of that nature.

In the end what matters is what is going on in people's daily lives. How are they feeling? What are their struggles, their frustrations? Do they feel like they have done everything right and are still being treated unfairly by the system? My journalistic background has been a tremendous asset for me in my political work, because there are so many pollsters who are just number-crunchers. If you think about what journalists do, we're trying to uncover the story. We can use legitimate research techniques, whether it's qualitative, through focus groups or polling. But to be successful as a candidate, you need to make a connection with voters without catering to them. How can you connect your values to theirs? When a candidate can do that, we see the strongest campaigns.

There is at least six decades of political science and other research showing that the American voter is not very sophisticated. In your experience, is that true? How does that impact your approach to politics?

Never underestimate the American voter. It doesn't matter how sophisticated they may or may not be, as determined by you or me or some other expert. Your job as a candidate, or someone advising a party or campaign, is not to preach to the sophisticated voter. Your job is to understand the values, the frustrations and the pain points that the average voter is bringing to the table. You've got to meet them where they are. Again, you should not cater to voters. But if you as a candidate are not going to connect with what matters in their lives — and even more so how the story of your life resonates with their experiences — what you say is going to fall on deaf ears. 

One of the common errors we see among the Democrats, and too many among the media class, and liberals and progressives more generally, is this narrative about how "working class" and independent voters do not understand what their "real" interests are, and that they have somehow been bamboozled by "culture war" issues. When I talk to white liberals on this issue, I say that these voters know exactly what they are voting for. They just define their interests differently from yours. Their rationality is not your rationality, and you had best accept that fact.

That is true. As I said earlier, do not presume that voters are defining their self-interest in the same terms that you are. For example, let's consider the Republican Party and evangelical Christians. As a group, their interests are not driven by economics. Instead, right-wing evangelicals are driven by their faith and religion. To be clear, I do not believe that we should cater to them in a pluralistic democracy and government. They should not be the driving force in our country. But you do need to understand what evangelical Christians are voting for in order to fully understand our politics right now.

I'm also not saying that the Democrats need to change their policies to try to win over conservative Christians. However, you can understand the different types of things, the multiple types of self-interest, that are operative among a given group of voters. Then you can craft a way to communicate your message to them.

I tell the politicians that I work with that, in the end, presidential elections are about big things and not small things. They're about the future, not the past. They're about the lives of the voters, not your personal biography. That doesn't mean that your life story is unimportant. But you have to connect your biography to how the voters think about their own lives and experiences.

Why does Donald Trump have such enduring popularity and power? Is he a savant? Is it his consultants and media people? Is he able to mine rage and hatred in a way that the Democrats can't stop? What do Trump and his inner circle understand about American politics and public opinion that too many others do not?

Donald Trump met a moment. There was a story that was on the front page of the New York Times toward the end of 2016. The headline and lede were basically that voters saw Trump as a big risk who may be worth it. What we missed during Hillary Clinton's campaign was how much of an anti-establishment moment we were living in. This was happening around the world with Boris Johnson, Viktor Orbán, other populist leaders who were outside of the traditional establishment. That was Trump. That's his appeal. Trump's voters and many others felt like the establishment had been failing them economically, politically and culturally. Moreover, this sense of upset and resentment was focused on both Republicans and Democrats.

Remember, Trump did not win the popular vote. A common narrative we heard was that the polls were wrong. That's not true. The polls were national polls, and Hillary Clinton basically won them by the predicted margin. Unfortunately, we had a campaign that decided to stop polling in Pennsylvania, Michigan and Wisconsin, the three states in the so-called blue wall for Democrats in the Electoral College. Even worse, they decided to stop polling on Labor Day. Congratulations, you lost the presidential election!

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In the end, Trump benefited from being of that moment and from running against a candidate who embodied so much of what many Americans were angry about. She was a very strong candidate with great credentials. But Hillary Clinton had been a fixture in Washington for two and a half decades. If you are in an anti-establishment moment, the bomb-thrower who says he is going to shake things up becomes very attractive to voters. They didn't care about Trump's résumé. That was the dynamic in the 2016 presidential campaign. Many politicos, like myself, did not grasp what was happening at the time.

Hillary Clinton basically told the truth about Trump's voters being a "basket of deplorables." Her truth-telling on the disaster that would afflict the country if Trump won has been vindicated. Having said, her truth-telling may not have been the smartest political move. As they say, history will have the final judgment.

In the last week of the campaign, a video comes out with Donald Trump bragging about grabbing women by their genitals. What was the biggest story in the last week of the campaign? Hillary's emails. Anytime Hillary Clinton's emails were in the news it was going to be a bad week for us. Even though Hillary's emails were a non-story that had been known for months, it became the focal point of the news media's coverage during the last week of the campaign. The story was not Trump, for all intents and purposes, sexually assaulting women. There are things you can control in campaigns, and other things you can't. I hope journalists and editors look back at their choices during the 2016 campaign and reconsider what they did and how Trump's behavior and that hot-mic audio were more important than Hillary's emails. 

Hillary did warn people about Trump. But her mistake was the language she used. You should never characterize voters that way. Let's be clear: there were mistakes made in that campaign. How do you stop polling in three states that are essential to your victory? It was absurd. I'm not going to try to convict the campaign, but I am also not going to absolve it of its mistakes. The "deplorables" comment gave Trump and the Republicans lots of fodder.

If Donald Trump was appealing to the so-called white working class — a group of people who have a sense of aggrievement that elites looked down upon them — calling them a basket of deplorables is a big mistake. That comment makes Hillary into a representation of those elites they are angry at. As a strategic matter, make the campaign about Trump, show that he is the deplorable one.

What do you think about the Democrats' current strategy of boosting the most extreme pro-Trump Republican candidates in certain key races, as a way weakening them with undecided or independent voters?

I do not believe that playing that kind of tactical game is how you win elections. The way to win is by having a strategy that defines very clearly why you are the better person for that job. Find the voters you need to win the election and then persuade them to your side.

There is an old idea that public opinion is a chorus or thermometer of the public mood. In the aggregate, what has American public opinion been saying these last few months?

What that chorus is telling us is that we the voters are going to align with the candidates who are addressing the issues that affect our lives the most and issues we care the most about. We are going to back those candidates who seem to be on our side and fighting for the same things we are concerned about. The vote on women's reproductive rights in Kansas, which is a red state, was very instructive. Among independents especially, there are some issues where Republicans have gone too far to the right. These are things like guns — we have had too many mass slaughters in this country. What Democrats have to do is to continue to state their case on abortion choice, on taxes, on making the rich and corporations pay their fair share. The vast majority of the public supports the Democrats on these issues. In addition, more swing voters are where Democrats are when it comes to the economy.

The Republicans are captive to the more extreme wing of their party on so many issues that the American people care about. Democrats should be exploiting that fact and presenting a clear option to those voters they can win over — and those voters exist. But can the Democrats do it consistently? Can they focus their message and outreach in a disciplined way? There is one huge obstacle for the Democrats, and that is how reapportionment favors the Republicans. The Republicans control more state legislatures and governor's houses than do the Democrats. They have a serious structural advantage that the Democrats have to overcome.

Conventional wisdom is that the Republicans are much better storytellers than the Democrats. As a function of that, they are also better at the practical work of winning elections and getting their policies put in place. What do today's Republicans, and especially the Trump movement, understand about emotions and how to manipulate them that Democrats do not?

I disagree with the premise. The Republicans have created a secure base. They don't play to the middle much anymore. They do an excellent job of that — they have a very strong connection with evangelical Christians, for instance. In addition, the Republicans win at the state and congressional levels because they focus so much attention there. By comparison, on the national level the Republicans have done much worse, in terms of winning the presidency.  

In terms of messaging, should Trump and all the harm he has done be the focal point of Democratic messaging? Trump and the Republicans are an existential threat to American democracy and society. Shouldn't that be foregrounded by the Democrats?

Unless and until Donald Trump is a candidate, keep him out of it. There is no reason to bring him into it. The challenge right now, and where the focus should be, is on the Republicans. Trump is not on the ballot for the Senate or Congress in 2022. If we start talking about Trump, it looks like Joe Biden is afraid of Trump. He's not a presidential candidate yet, and he may never be.

Will the Dobbs decision be the game-changer for the midterms that many observers are predicting?

It is going to be a very powerful dynamic in the values debate. Dobbs is putting Republicans on defense. A Republican-controlled Supreme Court made the decision to end Roe v. Wade. You cannot ignore that vote in Kansas. The Republicans are going to lose a lot of voters over abortion rights. The Dobbs decision is not going to win the Republicans any new supporters. They already have that base vote.  

What is your general sense of the midterms at this point?

Historically, over the past four decades first-term midterms have not been good for the president's party — with one exception, which was for George W. Bush in 2002, after the 9/11 attack. That is the political law of inertia: Every action has an equal and opposite reaction.  But I also caution not to read that dynamic as a determinative or final verdict on the incumbent. For example, Democrats lost big in 2010, and in 2012 Barack Obama became only the seventh president in history to be elected and re-elected with more than 50% of the vote both times.

If the Democrats somehow manage to do better than expected, meaning that they hold the House and the Senate, what lessons should they learn? Likewise, what if they lose, as many or most are predicting? What are the lessons there?

If Democrats do better than expected, I would say this: Be rigorous in analyzing and understanding where and why Democrats won and what differentiated them from Democrats who lost, and assess why that happened. Focus in on the structural, cultural or other issues that Democrats can use to win more going forward. Contrast those winning results with where we lost seats we expected to win. Do an honest assessment of why that happened and what adjustments you can make in terms of issues or candidates in those districts or states without compromising on core Democratic values.

Likewise, if the Democrats end up doing worse than expected, do a similar diagnosis. Contrast the winners and losers, their approach and issues, to assess what worked in those tough districts and what didn't.

Imagine that you are a doctor of democracy and politics. How would you diagnose American democracy right now? How is the patient doing? 

The patient is struggling because it's fighting off multiple viruses at the same time. These viruses are insidious and there are many of them. The Republican Party is contributing much more to the illness than to the remedy. What we have to do as Democrats is to highlight that fact: The Republicans are making American democracy and society sicker.