“They’re a rotten crowd,” I shouted across the lawn. “You’re worth the whole damn bunch put together.”
— F. Scott Fitzgerald, The Great Gatsby

I. “LOVE WILL MAKE YOU DO WRONG”

In the waning days of President Barack Obama’s administration, he and his wife, Michelle, hosted a farewell party, the full import of which no one could then grasp. It was late October, Friday the 21st, and the president had spent many of the previous weeks, as he would spend the two subsequent weeks, campaigning for the Democratic presidential nominee, Hillary Clinton. Things were looking up. Polls in the crucial states of Virginia and Pennsylvania showed Clinton with solid advantages. The formidable GOP strongholds of Georgia and Texas were said to be under threat. The moment seemed to buoy Obama. He had been light on his feet in these last few weeks, cracking jokes at the expense of Republican opponents and laughing off hecklers. At a rally in Orlando on October 28, he greeted a student who would be introducing him by dancing toward her and then noting that the song playing over the loudspeakers—the Gap Band’s “Outstanding”—was older than she was. “This is classic!” he said. Then he flashed the smile that had launched America’s first black presidency, and started dancing again. Three months still remained before Inauguration Day, but staffers had already begun to count down the days. They did this with a mix of pride and longing—like college seniors in early May. They had no sense of the world they were graduating into. None of us did. 

The farewell party, presented by BET (Black Entertainment Television), was the last in a series of concerts the first couple had hosted at the White House. Guests were asked to arrive at 5:30 p.m. By 6, two long lines stretched behind the Treasury Building, where the Secret Service was checking names. The people in these lines were, in the main, black, and their humor reflected it. The brisker queue was dubbed the “good-hair line” by one guest, and there was laughter at the prospect of the Secret Service subjecting us all to a “brown-paper-bag test.” This did not come to pass, but security was tight. Several guests were told to stand in a makeshift pen and wait to have their backgrounds checked a second time. 

Dave Chappelle was there. He coolly explained the peril and promise of comedy in what was then still only a remotely potential Donald Trump presidency: “I mean, we never had a guy have his own pussygate scandal.” Everyone laughed. A few weeks later, he would be roundly criticized for telling a crowd at the Cutting Room, in New York, that he had voted for Clinton but did not feel good about it. “She’s going to be on a coin someday,” Chappelle said. “And her behavior has not been coinworthy.” But on this crisp October night, everything felt inevitable and grand. There was a slight wind. It had been in the 80s for much of that week. Now, as the sun set, the season remembered its name. Women shivered in their cocktail dresses. Gentlemen chivalrously handed over their suit coats. But when Naomi Campbell strolled past the security pen in a sleeveless number, she seemed as invulnerable as ever. 

Cellphones were confiscated to prevent surreptitious recordings
from leaking out. (This effort was unsuccessful. The next day, a
partygoer would tweet a video of the leader of the free world
dancing to Drake’s “Hotline Bling.”) After withstanding the
barrage of security, guests were welcomed into the East Wing
of the White House, and then ushered back out into the night,
where they boarded a succession of orange-and-green trolleys.
The singer and actress Janelle Monáe, her famous and fantastic
pompadour preceding her, stepped on board and joked with a
companion about the historical import of “sitting in the back of
the bus.” She took a seat three rows from the front and hummed
into the night. The trolley dropped the guests on the South Lawn,
in front of a giant tent. The South Lawn’s fountain was lit up with
blue lights. The White House proper loomed like a ghost in the
distance. I heard the band, inside, beginning to play Al Green’s
“Let’s Stay Together.”