The Art of Failing Upward

On Tuesday evening, denizens of Donald Trump’s Washington, D.C., gathered at a tavern on the capital’s southwest waterfront to toast one of the most widely ridiculed White House press secretaries in history.

The official occasion for the night’s festivities was the release of Sean Spicer’s new memoir, The Briefing. But the event doubled as a more general celebration of Spicer’s lucrative return to D.C.’s polite society—if he’d ever really left—and a reminder that even those who serve in the establishment-reviled Trump administration are guaranteed access to that grand, bipartisan tradition of failing upward in the swamp.

Now, it’s worth noting that there are certain genre conventions to be adhered to when writing a proper Washington-book-party dispatch. Scene-setting details are established with descriptions of the venue’s decor (black-and-white checkerboard floors, stylized photos of topless women) and the appetizers being served by waiters (tater tots on silver trays, chicken nuggets with toothpicks in them). The notables in attendance are noted, the author of the hour is quoted, and a smattering of gossipy tidbits are inserted to illustrate—not too heavy-handedly, mind you—the incestuousness of America’s political class.

As a consumer and occasional producer of this type of journalism, I am well acquainted with the genre. And yet somehow, on Tuesday night, going through the motions of amused detachment felt insufficient to justify my participation. A nagging feeling of complicity persisted.

And so, when Spicer—wearing dark jeans, a blue blazer, and a pleased grin—paused between book signings to greet me with an exclamation of, “Wow, looks like I’ve really made it!” it was all I could do to stifle a weary sigh before responding, simply, “I’m here.”

There was a time, not too long ago, when people were forecasting a gloomy outlook for Spicer’s post–White House career. His six months behind the podium as President Trump’s press secretary had been defined in the public consciousness by a blur of brazen lies and barely trying spin—his sputtering press briefings immortalized on Saturday Night Live, his legacy shaped by his most humiliating meltdowns. (Remember the “Holocaust centers”?)

When he resigned, outside observers mercifully unschooled in the ways of Washington assumed that his role as an agent of misinformation—and his willing participation in Trump’s culture war on the press—would result in some sort of negative consequence for the career communications professional.

How quaint.

It’s true that Spicer struggled to land the kind of cable-news contract typically offered to high-profile White House departees. (Network insiders worried, apparently without irony, that he lacked “credibility.”) But then came the offers on the high-dollar speaking circuit (where he reportedly sought north of $30,000 a speech), and the prestigious fellowship at the Harvard Kennedy School, and the book deal, and the talk-show pilot, and the gig at the cash-flush America First super PAC, and—well, it’s safe to say now that Spicer has landed on his feet.

Standing amid a throng of fans, his face illuminated by camera light—the event was being covered by C-SPAN and RT, as well as another roving camera crew—Spicer reveled in his triumph.

“I’m having a blast and enjoying this, and frankly I’m blessed by the amount of opportunities that have come my way,” Spicer told me. “And that’s a pretty good way to go through life.”

Of course, outside the party, the coverage of his book had been less than glowing. During an interview with the BBC, a host had flatly told Spicer, “You have corrupted discourse for the entire world by going along with [Trump’s] lies.” And in a Wall Street Journal review, the journalist Jonathan Karl had written that Spicer’s book was “much like his tenure as press secretary: short, littered with inaccuracies, and offering up one consistent theme: Mr. Trump can do no wrong.”

When I asked Spicer if he had read the Journal review, he made a point of appearing aggressively unfazed.

“To be honest with you, it’s sort of what I expected,” Spicer said. “Because part of the book talks about the problems with the elite media. I mean, they’re not gonna look at it favorably. So it’s not shocking.”

He was quick to remind me, however, that he’s gotten some good press, too—in The Washington Post and Washingtonian magazine, both of which had produced “excellent” articles in his estimation—and by the way, had he mentioned that he’s already sold out book-tour stops in San Francisco, and that he’ll be appearing at the Ronald Reagan Presidential Library? And before I had time to ask a follow-up question, he was on to the next fans in line, signing books, posing for pictures, and soaking up the joys of political celebrity untainted by accountability.  

The guests in attendance Tuesday didn’t include many A-listers; the bold-faced names of Trumpworld would likely turn up at Thursday night’s book event at the Trump International Hotel. But the politicos who did come told me that, even when Spicer was getting pummeled as press secretary, they never doubted his ability to make good once he left the job.

“I knew the talk circuit would eat him up, and I knew the base loved him because that was our audience,” said Jim Stinson, a conservative journalist who covered the Trump White House for the Laura Ingraham–founded website LifeZette. “From what I’m hearing, Trump alumni are worried: ‘Where do I work next?’ But you know, I don’t know if they should have that concern.”

Chris Warner, a native South African who has lived in Washington, D.C., for 12 years and works for the World Bank, said Spicer had benefitted from his willingness to admit (in a general way, at least) that he had made mistakes while working in the White House.

“I think the U.S. is incredibly forgiving,” Warner observed. “It seems that everybody is able to do a makeover if that’s what they want to do.”

Spicer knows this, of course. And so, when it came time for the night’s main event, he took his seat on stage for an interview with the Townhall editor Katie Pavlich and told his story—smiling sheepishly as he cast himself as a cockeyed optimist who came to the nation’s capital brimming with idealism, made a few mistakes along the way, but ended up working in the White House, never losing his sense of awe for the office of the presidency.

When Trump offered him the job of press secretary, Spicer said, “I had visions of The West Wing running through my head … It was sort of my American dream.”

A woman sitting near me leaned over to a friend, smiling and shaking her head with apparent admiration. “I love him so much,” she whispered.

I found my way to the exit shortly after that, leaving Spicer to enjoy his American dream.