Dastardly Cleverness in the Service of Good

It’s hard to stand for something if you’re not even sure what that something is. And many liberals have become unsure what liberalism is.

For a long time, few of us had to think much about it. Liberalism was just default political reality.

It was like water is for the young fish in David Foster Wallace’s famous parable: They can’t see the water, because it’s everywhere.

Let’s remember that the word “liberalism” doesn’t only refer to beliefs on the left. It’s also the name of the philosophy of freedom on which the United States and every other liberal democracy were founded. When Thomas Jefferson wrote “We hold these truths to be self-evident…” he was referring to the principles of this kind of liberalism.

But now we liberals are being forced to think about our default reality, because it’s being disrupted by two radical challenges from outside: one from the MAGA right and another from what’s commonly called the woke left — although the word “woke” needs some clarifying, which I’ll get to a little later.

The trouble is, it can be hard for liberals even to see these challenges for what they are. They don’t fit within our default reality.

More at substack.com/@spencercritchley.

With American democracy facing its greatest crisis since the Civil War as a corrupt autocrat returns to the presidency, I want to do my part, however small, to help right now.

So I’m going to try an experiment: writing a shorter, more tightly focused book, and releasing chapters as I write them. They’ll appear as posts and podcast episodes, like this one.

There are many reasons why we are where we are, and in this little book I’m not going to try to address all of them. Instead, I’m going to try to answer what I think are two of the most important but most poorly understood questions we’re facing:

How did Democrats, and liberals in general, get so bad at politics?

And what can they do about it?

More: dastardlycleverness.com/liberal-backbone-chapter-01

— Spencer

Ernest Hemingway is famous for the terse economy of his writing. And in one of the most resonant examples of that quality, he captured the essence of catastrophic failure in just a few words, in his novel The Sun Also Rises.

The alcoholic veteran Mike Campbell is asked how he went bankrupt.

“Two ways,” he says. “Gradually and then quickly.”

As it is with one person going broke, so it is with an entire economy crashing, or countless other catastrophes. There isn’t only a single failure, but a first, and then more — and then a cascade.

And so it is when a democracy fails: it happens slowly and then all at once.

Facing the possibility of a vindictive autocrat becoming president, the LA Times decides not to endorse his opponent, or anyone. Then the Washington Post does the same. Then USA Today and all the other Gannett newspapers follow.

Some of their journalist employees protest, but almost no one walks off the job; a few editorial board members are rare exceptions. We can feel for those who keep their heads down. Given the precarious state of journalism, they know that if they lose the job they have now, there's almost nowhere else for them to go.

Businesses, too, begin signaling their loyalty and obedience to the potential dictator. Their executives are driven by what they see as their duty to protect against risk — even as far larger risks gather. Nearly all their employees act essentially the same way.

And as the cascade accelerates across society, a democracy that has survived many shocks fails. The last shock is sudden, even though the preparation was long.

Until recently, it seemed unthinkable to most Americans that our democracy could fail. But it would be far from the first, as historians of democracy know well.

One of the most insightful is Robert Kagan, who until recently was a member of the Washington Post editorial board. Kagan immediately recognized the meaning of the Post’s endorsement surrender. He resigned. It wasn't the first time he had made such a choice. In 2016, he left the Republican Party after it nominated Donald Trump. He sounded an alarm in an essay for the Post called “This Is How Fascism Comes to America.”

But as Kagan’s principled choices demonstrate, fascism doesn’t have to come. Our democracy doesn’t have to fail.

Some failure cascades are like avalanches: impersonal and irresistible. But when a human system fails, each step is a choice by an individual human being — by each of us.

And sometimes, we make the right choice. Nothing is stopping us from doing that now, or at any time — nothing but our own character. “The fault is not in our stars, but in ourselves,” as Shakespeare’s Cassius tells Brutus, with the Roman Republic falling around them.

More: https://dastardlycleverness.com/slowly-and-then-all-at-once/

If we believe in democracy, I believe we have a responsibility not only to vote for it but to speak up for it, including to family and friends, despite how hard that might be. That doesn’t mean berating or insulting them. It can be done quietly and respectfully. In my own view it’s a mark of respect and even love to give people the whole truth about what we believe.

So I’ve written an appeal to a friend who's planning to vote for Donald Trumo, imploring them, before it’s too late, not to make a mistake I believe they’ll regret for the rest of their life. I hope it might be useful for you, however you plan to vote.

— Spencer

According to my guest this time, the United States is entering a Latino century, and that might be what saves our democracy.

Mike Madrid is a top expert on Latino voting, and in recent years he’s become a national leader in the bipartisan fight to save democracy.

He’s been the political director for the California Republican Party, a senior adviser to both Republicans and Democrats, and a co-founder of the never-Trump Lincoln Project.

Now Mike has a new book, called The Latino Century: How America’s Largest Minority Is Transforming Democracy. 

One of his goals for it is to help the Democratic Party win against MAGA authoritarianism. 

He’s worried, though, that Democrats have been slow to get the message about Latinos and their crucial role in the nation’s future. And he thinks that helps explain why so many Latinos have been moving towards the Republican Party, a development many Democrats find baffling. 

According to Mike, they’re baffled because they don’t understand Latinos or other minorities nearly as well as they think they do. He says too many Democratic candidates, strategists, and pundits think of minorities as theoretical stereotypes instead of as real people with complex lives. That’s why Democrats tend to assume immigration is the top issue for all Latino voters, for example, or that most want to be talked to in Spanish. Both of those assumptions may seem reasonable theoretically, but are often wrong in reality.

Mike argues that now more than ever, Democrats need to get reality right. That’s because first of all, the Latino vote can make the difference in crucial battleground states this year, including ones that may surprise you, like Wisconsin and North Carolina. And he believes that over the long haul, Latino voters can help revive all Americans’ faith in democratic institutions — and democracy itself.

— Spencer

Many liberals are deeply confused about how to respond to the campus protests over Gaza. And I think it’s an example of the confusion liberals are feeling generally over a lot of issues.

I believe much of the confusion can be traced to the assumption that all political opinions can fit on a single line, from left to right. 

For this one-dimensional, one-line model to work, there can only be one left and one right — but there are at least two lefts and two rights. And they’re not different as in further left or further right on the same line. They’re different as in not on the same line at all.

And the difference goes back to the rise of liberalism, accompanied by the rise of an anti-liberal left.

As we risk obliviously repeating catastrophic mistakes others have already made, Spencer Critchley has some thoughts about memory and freedom, from people who know the precious value of both.

Excerpt: "Most of us in the U.S. have been spared the necessity of knowing history, and instead have been able to live as if the world was created at our birth. But people in Central and Eastern Europe have already been trammeled by the history that has just now caught up with us. They’ve been trying to warn us for decades."

If you wanted to, you could consume nothing but presidential campaign coverage all day every day. But how much of it would leave you feeling better informed about casting what may be the most important vote of your life? Not better informed about the campaign as a sporting event, with all the expert play-by-play, color commentary, and stats. But better informed about questions that may not have easy, satisfying, or entertaining answers? Better prepared to think, and not just react?

On this episode of Dastardly Cleverness, we go hunting for that kind of election coverage, find a little, and try to supply some ourselves. I'm joined by two people I can always count on to leave me better informed.

Mike Madrid is a co-founder of the Lincoln Project and one of the country’s top political consultants, with special expertise on Latino voting trends. Mike previously served as the press secretary for the California Assembly Republican leader, as the political director for the California Republican Party, and as a senior adviser to both Republicans and Democrats. He’s the author of the upcoming book The Latino Century.

And Zach Friend has worked for multiple presidential campaigns, the White House Council of Economic Advisers, the U.S. Senate, and the U.S. House of Representatives, and has served for multiple terms as an elected official in Santa Cruz County, California. Zach is the author of the book On Message.

-- Spencer Critchley

By some measures, well over half of charities do little or no good. When similar charities are compared, the most effective ones can be up to 100 times more effective than the least. And there’s often a big mismatch between where donors direct their support and where the need and potential benefits are greatest.

A movement called effective altruism aims to make giving work better by identifying the most effective charities in the world and encouraging donors to support them generously and strategically.

There's been a lot of excitement about it, but lately it's also drawn critics of its ethical premises and the behavior of some who call themselves effective altruists.

In this episode Spencer explores both the promise challenges of effective altruism, in a fascinating conversation with one of the movement’s leaders, Luke Freeman, Executive Director of Giving What We Can.

There are lots of reasons to be cynical about the crisis in our politics. The trouble is, one of the biggest causes of that crisis is cynicism itself.

We should always be skeptical about politics. People aren’t angels, as James Madison reminded us.

But skepticism involves checking to find out what’s really going on, good or bad. Cynicism is just assuming that it’s all bad.

This is often mistaken for savviness, which lends cool-kids credibility to claims like “all politicians are crooks,” or “there’s no difference between the parties,” or “government never works.” Except none of those claims actually stands up to skeptical scrutiny.

Political journalists reinforce cynicism when they cover politics, day by day, as a dirty game in which all the players are more or less the same: self-interested schemers. NYU journalism professor Jay Rosen blames it on what he calls “the cult of savvy,” which rewards reporters for the cynicism of their coverage, when what we need from them is skepticism.

Skepticism is healthy, and necessary for democracy. You can’t say either about cynicism.

If we automatically accept cynical beliefs as true, we make them ever more likely to become true. People who work on behalf of hope gradually withdraw from the arena, leaving it to people all too happy to encourage despair. And those are people who do in fact have very bad motivations.

In this way cynicism reinforces itself and becomes a political death spiral.

Democracy can’t run on despair. But authoritarianism depends on it. This is why authoritarians like Vladimir Putin or Donald Trump don’t care that you know they’re lying — they want you to know they’re lying. It serves their interests if you conclude that everyone is a liar, and lose hope.  Then your only safe choice is to back the most powerful liar.

All this is why I wanted to talk this time about what has become a deeply unfashionable topic: morality in politics. Yes, it does exist, and in a democracy it must exist.

And once again I talk with Kevin Lewis and Zach Friend. 

Kevin has been a communications advisor and spokesman for former President Barack Obama, the White House, the Department of Justice, both Obama campaigns, and Meta.

Zach has worked for the White House Council of Economic Advisers, the U.S. Senate, the House of Representatives, and several presidential campaigns, including both of Obama’s. He’s currently an elected Supervisor in Santa Cruz County, California.

Both have seen lots of the good and bad in politics, but neither is a cynic.

— Spencer