Over Twitter, Kevin Drum asked me to identify the Democrats’ three biggest mistakes.

@haroldpollack What were the 3 biggest Dem errors?

— Kevin Drum (@kdrum) November 25, 2016

I have mixed feelings about answering that question. When a comprehensively dishonorable and unfit demagogue ascends to the presidency, all the traditional gatekeepers of our political system have failed: Both parties, the media, the electorate itself. Of course with an election this close, any number of things might have turned the outcome. FBI director Comey’s intercession was probably the decisive endgame factor. He’s not a Democrat.

And whatever mistakes Democrats made, the main responsibility resides with the Republican primary electorate who selected the worst nominee in generations, and with the Republican political professionals who enabled that nominee. They knew exactly who and what Trump was. They supported him anyway, often quietly hoping someone else would bring him down. Had Paul Ryan and George W Bush bluntly announced in late October that Trump is unfit to be president, America would have been spared what we are about to endure.

And Hillary Clinton did a lot right, a fact reflected in her clear popular vote victory. She clobbered Trump in three debates. Her policy shop was maybe the best assembled by any candidate ever. Many of her campaign commercials were outstanding. That should have been enough. It wasn’t.

Still, Democrats must be clear-eyed in assessing how this could have happened—and how we can ensure it doesn’t happen again. In no firm order, here are several mistakes we made*:

Creating the email and speech problems, and being brittle and defensive about cleaning them up. Yeah, the email scandal was blown wildly out of proportion. Clinton’s ethical blemishes and potential conflicts of interest are in every way dwarfed by Trump’s brazen behavior as President-elect. Still, she mishandled the email issue, and was brittle and defensive in responding. For all the anger among my fellow liberals about “Clinton rules,” the Clintons’ personal financial dealings did not serve their supporters well. Why on God’s green earth was she giving ridiculously overpaid speeches on Wall Street when she was the obvious heir apparent to the Obama presidency? I proudly supported Clinton over Sanders in the primary, but Sanders was right about the speech issues, and in asking to see what she said in return for a six-figure speaking fee.

That pattern of behavior and defensiveness created huge vulnerabilities for Trump to exploit. It wasn’t right or fair, but it was predictable. Many of us missed that. Because Hillary Clinton shares and would continue President Obama’s policy agenda, we assumed that she would command his voters. In fact, American voters regard these two people quite differently. This partly reflects real and poisonous sexism. But this also reflects the simple fact that President Obama has served the past eight years with an almost complete absence of scandal in both marital and financial realms. That contrast did not serve Hillary Clinton (or Bill Clinton) well.

Overconfidence and complacency across the political spectrum. Right up to Election Day, pretty much everyone across the political spectrum assumed Clinton would win. The ripple effects of that overconfidence greatly increased the probability that she would lose.

The media covered issues such as the Clinton Foundation with the critical eye one would focus on the future president. Donald Trump’s racism and his unethical practices were definitely covered, but for the most part his shortcomings were not treated with the seriousness and immediacy they would have been, had elite media seriously believed he would win. Look at the difference between November 7 and November 9 in the depth and tone of coverage applied to the practicalities of his business dealings. It was always obvious that he would be saddled with myriad conflicts of interest as a sitting president who owns a sprawling business empire. Few of us were particularly focused on that, because most of us were implicitly so sure this would be a moot point on November 9.

The Clinton campaign’s overconfidence was reflected in its huge investments to expand the map to states she didn’t need and wouldn’t get while they neglected rustbelt states she desperately needed and would lose by a sliver. That lack of battleground organizational capacity still puzzles me. On November 6, I had to drive my daughter back to college at Whitewater, Wisconsin. In 2012, I had done many GOTV near there. I saw almost nothing within an hour’s drive outside Madison and Milwaukee. I don’t recall any particular sense of urgency there.

Demography provided one reason for overconfidence. As both Nate Cohen and Ron Brownstein presciently noted, Democrats easily overestimated the demographic power and inevitability of the coalition which put President Obama in the White House. Indeed, Brownstein noted earlier this year that the worst-case scenario for Clinton would be that

Trump’s blue-collar blitz narrowly pushes him past her in some of the Rustbelt states she needs, while she cannot advance quite enough among minority and college-educated white voters to overcome his non-college-educated, non-urban, religiously devout coalition in Sunbelt states like North Carolina, Florida, Nevada, and Colorado, much less Arizona and Georgia. Transitioning between her party’s past and future, Hillary Clinton’s nightmare is that she might be caught awkwardly in between.

That’s exactly what happened.

That overconfidence showed up in other ways, as well. Throughout summer and fall, my Democratic friends constantly speculated about what Clinton should do, what Obama should do, what Sanders should do, to put Trump away, what Clinton was doing right or wrong, and more. Unlike 2008 and 2012, I heard much less about what we needed to do in ensuring a Clinton victory and in keeping Donald Trump out of the White House. Moderate Democrats weren’t particularly active. I didn’t see many Clinton lawn signs or coffee cups. I never got the sense that we were engaged in an urgent common enterprise to stave off catastrophe. Many of us arrogantly placed our trust in the Maginot Line of Big Data, which we wrongly viewed as an adequate substitute for Big Organizing in winning a national campaign.

Many on the left—including people who actually voted for Ralph Nader in Florida-were visibly diffident and passive. Some denigrating Hillary Clinton as a faux feminist and lying neoliberal warmonger, though some begrudgingly allowed that they would hold their noses pulling the lever for her on Election Day  to prevent a greater evil. Clinton’s strikingly progressive policy proposals and her decades of work on behalf of children, the uninsured, women and girls, were somehow redacted from much progressive conversation. In the cruelest turn, Jill Stein got substantially more votes in Michigan and Wisconsin than Trump’s margin of victory. I suspect that many Stein voters—and many of Clinton’s more responsible left critics—would have spoken and acted differently had they seriously considered the possibility that she would lose.

Signaling to older rural white voters that we didn’t want them, and indeed would leave them behind. Since Election Day, much has been written about how Democrats need to craft an economically populist message that reaches white working-class voters. Indeed we do. A majority of white voters—even women—shamefully embraced a bigoted demagogue who questioned President Obama’s citizenship, disparaged Muslims and Mexican immigrants, and bragged about assaulting women. There’s no way to excuse or explain away this huge moral failure of the American electorate. Democrats must also defend the values that underlay our diverse, multi-racial coalition, which expresses much of what’s best in America, and represents the future of this country.

That said, I share Bernie Sanders’ shame that Democrats didn’t engage older white working-class voters more effectively, that we weren’t more a part of their lives, that we didn’t build more of a relationship with people whose rural and post-industrial communities face such punishment in our new globalized economy. Many progressive voters have moved out of these communities. Democrats have been hammered in many local races in these areas. Democrats and liberals are no longer a daily organic presence. Conservative churches, veterans’ groups. and other Republican-friendly institutions civil society are still there, touching people’s lives and earning people’s trust.

Throughout 2016, our party triumphantly presented itself as the embodiment of America’s multi-cultural, multi-racial demographic future. Of course, our national convention was the peak expression of that triumphalism, featuring Mothers of the Movement, the electrifying speeches by Mr. Khan and the First Lady. I loved every moment. I believed that organizationally tight and incredibly moving convention sealed Clinton’s victory.

Looking back, though, I’m troubled when I imagine watching that convention through the eyes of my own late in-laws. They lived on a modest income caring for their disabled son. Janice was a bookkeeper, and Greg worked in a construction company in central New York. Both would have regarded Donald Trump as a personally disgusting con artist. But I’m not sure they would have seen much at that Democratic convention that spoke directly to them, that addressed the economic devastation in central New York that they and their neighbors had to witness in slow-motion, whose effects they deeply mourned. This was a real failure of messaging and engagement.

Many of the messages used to such effect against Mitt Romney might well have been deployed in 2016. To provide one small but telling example, the Republican platform’s economic components provided a target-rich environment. I heard virtually nothing about it. Republicans are now discussing Medicare vouchers and changes to ACA that would raise insurance rates for near-retirees. I heard almost nothing about that in the beautiful ads lambasting Trump’s character flaws without calling him to account on Republican policies.

They would have been unimpressed by Clinton’s hobnobbing with Wall Street moguls. My father-in-law imbibed of conservative talk radio. He was primed to believe that liberals looked down on rural, socially-conservative folk. Had they been the slightest bit Trump-curious, they would have been infuriated by Hillary Clinton’s “deplorables” comment-doubly so since the comment was delivered speaking about them to an upscale audience rather than to their faces. In the end, I doubt they would have voted for Clinton, disgusted as they would have been by Trump’s depredations.

As a matter of policy, Donald Trump has little to offer the rural communities he won. Although elite media ignored the substance, Hillary Clinton offered them far more. As a matter of human connection, we must acknowledge that these voters had reason to feel condescended to, that we were leaving them behind. That’s a dangerous combination. To their shame and ours, these voters retaliated in a bitterly racialized election.

Listening on election night to disturbing data trickling in from rural Pennsylvania, Michigan, and Wisconsin, I was taken back to my high school English class, when Mercutio’s recounted his fatal wound: “Tis not so deep as a well nor so wide as a church-door, but ’tis enough.”And I wept.

*Addendum: Only hours later, I would add two inter-related errors. 

First, Democrats underestimated the power of partisan polarization to bring Republican voters back to Trump.  At the end of the campaign, Trump showed just enough message discipline to hold the Republican coalition together, particularly after James Comey provided unexpected help. Appealing to Republican women gathered fewer votes than Clinton had hoped.

Second-and related-the Clinton campaign never was able to break through with a compelling economic policy narrative that ordinary voters could understood amidst the clutter. The Clinton campaign certainly tried, and they had good detailed plans to improve people’s lives. Yet they were never properly able to reach the broader public.