CHICAGO — When I asked Rahm Emanuel how he thinks Democrats around the country are doing in appealing to the middle class, he pretended he was about to pound the table with both hands: “That would be one physical expression,” he said.

“We don’t talk about and fight for the middle class like we are,” the famously expressive Chicago mayor said. “We believe we’re for them, but they don’t — if they don’t hear we’re for them, then we got a problem. It’s not just for the string of policies. It’s also a set of values that respect who they are in their lives.”


“We come off and can come off as a party disdainful of them,” he told me.

Emanuel didn’t curse during our conversation, but he might as well have. I asked him why he never does so on microphone, given how famously colorful his language is behind closed doors — ask pretty much anyone who’s had a conversation with him, and they’ll do an impression full of four-letter words used rarely out of anger, but of love with how they feel in his mouth and glee at the reaction he knows they bring out.

“You can’t find once in public a naughty word that would require me to put a quarter in the bad-word box at our home,” Emanuel said.

Emanuel has a unique vantage, 700 miles away from the endless drama in Washington, here on the fifth floor of City Hall, where we met just off his private office for POLITICO’s Off Message podcast. He was a top aide in the Clinton White House, and President Barack Obama’s first chief of staff. He met privately with President Donald Trump during the transition, making an appeal for cities. He’s still quietly advising top Democrats over the phone and on occasional trips back to D.C. about how to take on Trump and how to rethink what they’re doing themselves.

And Emanuel is worried. He thinks everyone in Washington is too focused on the crazy around Trump to see what’s actually going on — and what’s not.

Just take what’s not been in the headlines the past few weeks amid all the West Wing drama and turmoil — a proposed upheaval to the tax code unveiled without any detail about who would pay less, who would pay more and how — “totally unacceptable,” Emanuel said. Or the mounting tension with North Korea as Trump talks about canceling the trade deal with and air defense system over South Korea. Or Trump’s invitations to the Oval Office for anti-democratic leaders like Rodrigo Duterte of the Philippines.

“America’s word and America’s reliability is now in question,” Emanuel said. “Come and gone like that.”

Emanuel’s hometown has been on the receiving end of Trump’s fury at rallies and on Twitter, where the president has decried (sometimes not completely factually) the violence on the Chicago streets that spiked bloodily last year, with 3,550 shootings in 2016 that left 4,331 victims and 762 homicides overall.

A few days after the inauguration, Trump tweeted, “If Chicago doesn't fix the horrible ‘carnage’ going on, 228 shootings in 2017 with 42 killings (up 24% from 2016), I will send in the Feds!”

That was followed up with nothing, Emanuel said. And he’d take help, but Trump seems more interested in the politics of talking “stereotypes” of cities to voters in Wisconsin and Michigan than doing anything about it.

“He’s attacked Atlanta, he’s attacked Philadelphia, he’s attacked New York, he’s attacked the gangs there, he’s attacked Chicago. I notice he never attacks suburban or rural areas for their opiate crisis. He talks about how to solve those problems,” Emanuel said. “You have a huge opiate crisis in the suburbs, massive opiate/heroin crisis. Now, there, they don’t get stereotyped or characterized. They get empathy.”

The grandson of an immigrant who arrived in Chicago, Emanuel takes the subject of immigration personally. But in December, when he went to see the then-president-elect in Trump Tower to appeal for a more welcoming approach to immigration, he made the case not on morals, but on Trump’s wallet.

“‘You know, you don’t invest in cities that are hostile to immigrants,’” Emanuel said he told Trump. “‘Why? They’re dynamic. They have new people coming in all the time. They have the energy of an immigrant culture, which is they’re starting small businesses, they’re hardworking, their kids are striving in school.’”

Emanuel went on: “I said, ‘I can make the moral argument. I want to talk to the part of your brain that’s a real estate developer. Look at the cities you invest in. They’re all welcoming.’”

So did it work?

“Obviously, no,” Emanuel said. “Clearly, I wasn’t as persuasive as I was hoping to be.”

He acknowledges how much trouble Democrats are in, and he makes a show of saying, “I used to do this for a living,” to coquettishly brush away, for half a second, a question about what his party should do now. Same as when he was actually Democratic Congressional Campaign Committee chairman in 2006, Emanuel advises: Look to the suburbs, find the moderates.

“Talking to ourselves and persuading ourselves,” Emanuel said, “is not going to be the way you get to a majority.”

Take the mayor’s race in Omaha, Nebraska, where Democrats have divided over supporting Heath Mello, who co-sponsored several bills restricting abortion in the state Senate. Cut it out, Emanuel said, and figure out how to win that race.

He could already hear the same complaints he faced in 2006, when the base of the party said he was selling out to the right to win.

“Now, somebody may say I’m unprincipled or I’m being too pragmatic, but it’s not like the character of the party and our values around the ability to give women of all walks of life choice is going to be fundamentally changed because of what happens in Omaha,” Emanuel said. “That’s a part of politics, and that’s acceptable.”