In Chicago, it’s back to the future for Democrats

The convention vibe is forward-thinking (free vasectomies nearby!) but high on nostalgia (please welcome Jimmy Eat World!).

10 min
Partygoers dance at the Hotties for Harris event during the Democratic National Convention in Chicago on Wednesday. (Nick Oxford for The Washington Post)

CHICAGO — “This feels like 2008. It’s the dawn of something new.”

Wait, what?

“As far as I know, time only moves in one direction — ”

This is Tim Daly, from the NBC sitcom “Wings,” which ended 11 years before 2008.

“ — though I’m sure some astrophysicists would argue that one with me.”

We are not astrophysicists, but we might argue that time moves in many directions at the Democratic National Convention. We are heading “FORWARD” according to the signs designed by Shepard Fairey, featuring a portrait of Vice President Kamala Harris, that transport us back to the “HOPE” poster he created 16 years ago for Barack Obama. “We’re not going back!” conventioneers chant before jumping on shuttles to see John Legend perform at Illinois Gov. JB Pritzker’s lavish party in a former Morton Salt warehouse (“I’m fired up and ready to gooooo,” Legend sings).

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It’s 2024, but the city is crawling with celebrities and pop culture from recent history (Daly, Common, the redhead from “Modern Family” and the bowling-ball-shaped brother-in-law from “Breaking Bad”). Second gentleman Doug Emhoff is at an after-party doing an impression of Borat (“Mah wiiiife”), as if it’s 2006, and then taking the stage Tuesday to the New Radicals, as if it’s 1998. A giant “Daily Show” billboard featuring Jon Stewart looms above downtown, as if it’s 2010. And former president Barack Obama is onstage reminding a rabid crowd that even if history doesn’t repeat itself, it does rhyme (“Yes she can,” he says).

Is it possible to be nostalgic for the future?

Time moves weird here. Sometimes it crawls.

“I was trapped on that bus for two hours,” a reporter says, upon arriving at the United Center on the first night of the proceedings. “And then in line for infinity hours more.”

And sometimes time skips ahead at warp speed.

Just one month ago it seemed like the Democratic National Convention was bound to be more funeral than shotgun wedding. But then President Joe Biden decided not to seek reelection, and Democrats decided they actually loved Harris, and suddenly the party was readyyy to paaartyyy (that’s a “Bridesmaids” reference from 2011). Thousands more Democrats wanted to volunteer at the convention.

“​​The phones started ringing off the hook 20 days ago, and they haven’t stopped ringing,” Pritzker told The Washington Post in his downtown Chicago office last week.

Jaimey Sexton, a Chicago-based Democratic operative, says he had been flooded with last-minute party pleas: Can you help me find a DJ? A lighting vendor? A venue?

Sarah Finlayson-Banasiak, a Chicago event planner, said she suddenly found herself trying to buy up every blue floral centerpiece she could find for her new clientele.

“A lot can happen quickly,” says podcast host Jon Lovett, the former Obama speechwriter. He would know. Earlier this summer Lovett went off the grid to film the turn-of-the-millennium reality show “Survivor” (still on the air!); when he returned to civilization, Lovett had what felt like years of catching up to do.

“I’d missed Trump being convicted,” he says. “I missed the fact that Samuel Alito flew insurrection flags outside of his house, and then the news just moved on. I missed the fact that RFK Jr. apparently has brain worms. I missed ‘beach blond butch body.’” (If you can’t remember all these things, don’t worry, they were all a million memes ago.)

It’s the third day of the convention now (that was fast), and Lovett is fresh off a game of cornhole inside the CNN-Politico Grill — the invite-only eatery whose security, according to the woman checking IDs at the door, is “tougher than the Secret Service.”

Now Lovett is chatting with the biographer Walter Isaacson about how great the speeches were the night before.

“We had Doug!” he says. “And Michelle and Barack Obama!”

“The best three speeches in a row I’ve seen,” says Isaacson.

Isaacson, perhaps feeling like things are moving a little too quickly, pumps the brakes on the excitement.

“There’s a little bit of a bubble,” he says, cocooned inside the perimeters of both the Secret Service and the CNN-Politico Grill. “When this is over, there’s still a lot of work to be done.”

But the work can wait. It’s time to party.

Jimmy Eat World takes the stage at the House of Blues around midnight on Monday night — that’s right, we’re moving back in time now; try to keep up — filling the venue with the aggressive strums of early-aughts rhythm guitar. It’s a party thrown by the Arizona and Wisconsin Democrats, but it feels more Wisconsin than Arizona, with the high concentration of summer-weight flannel and camo Harris-Walz hats. The inside of the legendary music hall is dark, the floor is sticky, and out-of-towners dare each other to try shots of Malört, a local liquor that tastes like grapefruit pith and truck tires. Ben Wikler, chair of the Wisconsin Democrats, is still vibing from Jimmy Eat World’s “The Middle” (which the band played, it should be noted, at the end of the show). “I’m so fired up!” Wikler hollers by the bar.

A month ago, Wikler worried whether he could fill the venue; by convention time, his team was turning down tons of requests. People “sense something is happening, they want to be there when history took place,” he says. A new feeling, reminiscent of an old time. “I can see echoes of ’08, with the whole new energy of this moment.”

At a nightclub uptown, hip-hop producer Lil Jon is in the DJ booth at the Georgia Democrats’ “Southern Soul Party.” He’s spinning a mix of wedding dance floor favorites and his own hits, flooding the darkness with confetti, lasers or a funnel of smoke to match the mood. It’s a packed, sweaty house that erupts when Lil Jon plays his hit “Get Low,” an old song with a new lyric: To the windowwwwww — to the Walz!

Democrats are still in their honeymoon phase with the former high school football coach and current Minnesota Gov. Tim Walz. Attendees at a happy hour hosted by Pennsylvania Gov. Josh Shapiro elbow their way through the crowd for the chance to meet the man who could have been the VP nominee (“It’s f---ing insane,” says an onlooking woman. “They’re all feral for him.”)

California’s Gavin Newsom — another governor whose aspirations for higher office may have been delayed given the “Game of Thrones” (2011) of it all — is still working the rooms and the cameras around here with his cinematic grin. In an elevator, headed to the TV network stations, Newsom talks about his frantic schedule as if it was plodding along: “Meetings. Meetings. Meetings. A lot of meetings. Then another meeting. Meetings.”

Later that night, there’s a party called “Hotties for Harris” with 200 content creators and influencers. And there’s a real fear about what the year 2025 might look like if it falls into the wrong hands.

“F*ck Project 2025,” read the condoms being handed out at the Hotties party — a reference to a plan, written by allies of former president Donald Trump, for how to gut the government should Republicans take control of Washington in November.

Speaking of condoms: Contraception is a big theme this week in Chicago, as if the Democrats are exploring any way to prevent certain outcomes.

Eight blocks from the United Center, Planned Parenthood sent a mobile health clinic — a vinyl-wrapped trailer with an examination bed and ultrasound machine — to perform vasectomies and dole out abortion medication.

“What we can provide from state to state is so dramatic,” says Margaret Baum, one of the doctors inside the trailer. “So by driving, you know, 20 minutes from my house, the type of health care that I can provide in Illinois is dramatically different than the type of health care that I can provide in Missouri, because of legal restrictions.”

To put it another way: In America, you can time travel backward while driving forward.

On Monday, nine men underwent vasectomies. They were sent on their way with care packages: ice packs, T-shirts that said “Bans off our bodies” and a $20 gift card to the Wieners Circle, a Lincoln Park hot dog joint.

There was a group of antiabortion protesters camped out by the trailer. When Baum’s first vasectomized guy came out, the protesters screamed at him, “You are still a mother!”

Mere feet away, past a few portable toilets, was Freeda. Freeda is a 20-foot-tall inflatable intrauterine device.

“The first thing most people do is stop and stare, because that’s what you generally do when you see a 20-foot-tall IUD, but we’ve [had] people ask if she’s a chromosome, or a torpedo,” said Meghna Ravi, a digital producer at Trilogy Interactive, an advertising firm that worked with Americans for Contraception to bring Freeda to life — with the goal of encouraging nonpolitical conversations about birth control and contraception (Freeda was born June 5, the same day that the Right to Contraception Act was defeated by Republicans in the Senate).

“Freeda is a cool girl,” said Hannah Tuohy, a strategist at Trilogy. “She’s having a cool-girl summer.”

“Freeda was brat,” Ravi added. “Now, she’s very demure, she’s very mindful.”

Finally, some references that aren’t 15 to 25 years old. (And yet they already feel way overdone, don’t they?)

And speaking of overdone: Ezra Klein is suddenly relevant again, as if it’s 2009. Did his early doubts, podcasted into the ether, help open the trap door under Biden? “The only thing happening here was saying what everybody was seeing,” Klein told New York magazine.

After the convention, Klein is off to Burning Man. By Wednesday, Freeda had already left for it.

On Thursday morning, CNN reported that the Chicks would sing the national anthem on the convention stage, before Harris formally accepted the Democratic nomination for president. (In the recent past, the Chicks were called the Dixie Chicks, but the old name was too backward-looking.)

“I’ve been to a lot of these,” Daly says. (Tim Daly again! Well, you can’t spell “time” without “tim.”) He is still standing outside of the United Center, on the third night of the convention. When it comes to conventions, he’s always around: in Denver in 2008, in Philadelphia in 2016. As an advocate for public arts education, he was even at the Republican National Convention last month in Milwaukee.

“There was a lot of energy,” Daly says, “but it was dark. Very dark.”

Democrats here worry that the dark forces could triumph in November. But for the first time in months, they don’t seem as worried about the future. After all, it kind of feels like they already lived through it.

Andrade reported from Washington.

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