Cinderella Man

On a phone call Thursday morning, I tried to impress a former White House speechwriter by mentioning casually that I would be attending the insider-famous Gridiron Dinner Saturday night—invited by a Washington Speechwriter Friend of our mutual acquaintance. 

Was she going? No, she wasn’t. “I wish I were,” she said, graciously.

My mission suavely accomplished, I then heard myself blurt out, “I’ve never worn a tuxedo before!” (“How can that be?” she muttered in genuine wonder.)

My subtle sense of insecurity must have also been detected by the woman barber in my Chicago neighborhood Thursday afternoon, to whom I went for a beard trim. To explain this extravagance, I told her I wanted to look tidy for a fancy dinner I would be attending over the weekend. I mentioned that our governor, J.B. Pritzker, would be speaking. And that I would be wearing a tuxedo (with tails!).

A scheduled 15-minute appointment ran to 30, as she prepped me meticulously for the big event. 

At one point, she asked, “Are you going to have a few notecards in your pockets?”

“What for?” I asked.

“Maybe with just a few things on them, to say to people.”

“Good idea,” I told her.

And then I reassured her that I’d have a notebook, instead. To write things down, that I heard from other people.

“Oh, that’s a good idea,” she said.

***

I developed a general distaste for Washington political humor events years before I became editor of Vital Speeches of the Day magazine and subsequently founded the Professional Speechwriters Association, and my opinion ostensibly began to matter even a little.

It was the bitter year of 2004, when President George W. Bush used the White House Correspondents’ Dinner, a showbiz version of the Gridiron gathering, to publicly poke fun at his administration’s claims that Iraq had weapons of mass destruction that necessitated a U.S. invasion of that country a little more than a year before. In the scandalous absence of such evidence, Bush showed a mock slideshow of himself looking under furniture around the Oval Office, “Those weapons of mass destruction have got to be in here somewhere.”

Massachusetts Democratic Senator John Kerry, who would go on to lose that fall’s presidential election to Bush, retorted afterward, “If George Bush thinks his deceptive rationale for going to war is a laughing matter, then he’s even more out of touch than we thought. Unfortunately for the president, this is not a joke.” He added: “585 American soldiers have been killed in Iraq in the last year, 3,354 have been wounded and there’s no end in sight. George Bush sold us on going to war with Iraq based on the threat of weapons of mass destruction. But we still haven’t found them, and now he thinks that’s funny?”

In intervening years, that was the example I used in many debates with my Washington Speechwriter Friend, who writes jokes for these kinds of events. How are regular Americans supposed to feel about D.C. politicians and journalists getting together to laugh it up about consequential policies they’re making and disseminating? Just more like regular Americans usually feel: mocked, by smug people in gowns and tuxedos.

My Washington Speechwriter Friend always counters, in his good-humored way, that these sorts of events represent more than one night’s détente-through-diversion. That the humor—especially the self-deprecating kind—is a way for opposing parties to recognize reality through laughter. If we can all laugh about a thing together, we (at least) still share something, that perhaps can be built on. By his logic, the more divided Washington and the nation are, the more useful are these D.C. comedy nights.

That’s where our conversations usually trail off, for another year.

But this year, my Washington Speechwriter Friend invited me to attend Gridiron. My first answer was a spastic “no,” followed hours later by a soul-querying “maybe” and not long after by a gratefully enthusiastic, “yes.” I wanted to experience this thing, one time, from the inside.

***

The Washington Speechwriter Friend invited Another Speechwriter Friend to join us. That friend and I were sharing a room at the Mayflower Hotel. I’ve rarely experienced a more serious moment, and neither have you, than the reverent silence in which that friend and I fastened our cufflinks and our button studs, and folded our pocket squares.

But when we arrived at the J.W. Marriott, we were put amazingly at ease. And not only by our Washington Speechwriter Friend, who was delighted to introduce us to his favorite people in the world he has inhabited for more than 30 years on the speechwriter-y fringes of D.C. politics—and to introduce those people to us. But also by the approximately 600 insiders themselves, who instantly appeared to us—Another Speechwriter Friend corroborated this with me during one of our six nightcaps afterward—not as Masters of the American Universe, as D.C. outsiders might imagine (and as I imagined as back when I was a D.C. outsider, last week), but more like us, grateful, in the middle of a workaday life, to have something Instagram-worthy to do, on a Saturday night.

“The dinner is on the record, but the content is embargoed until the dinner ends,” read the official dinner guide. “It is not televised. There is an absolute prohibition on photos and pictures from inside the ballroom during the dinner, but feel free to take pictures at the reception or the after party. We ask that you refrain from posting on social media until the dinner concludes.”

But what about a picture just outside the ballroom, with your absolute favorite Sunday morning news anchor Margaret Brennan in the background? 

Apologies, but this event does give the mind time to wander, beginning as it does at Seven Sharp and ending as it does at Ten Thirty Ish, with so much delightfully well-rehearsed and mostly ignored talent-show foolishment in the middle.

The event begins with a traditional Gridiron Club president’s “speech in the dark”—a series of jokes delivered this year by President Jackie Calmes of the L.A. Times in the weirdly wonderful pitch black. These jokes are conscientiously crafted in collaboration with a writer who knows and deeply cares about the “singe, don’t burn” Gridiron motto that has guided the previous 140 Gridiron dinners. This speech might be dubbed the State of the Union’s Sense of Humor, and going by the sound of this one, that sense of humor is (somehow) still strong.

Then the U.S. Marine Band plays the national anthem, for which everyone stands and remains silent—and then a few other patriotic tunes including “America the Beautiful,” which everyone talks over (making an odd sound).

Then, many humorous musical numbers, about Trump’s asshole-ism, AI, Mamdani, Kristi Noem and Corey Lewandowski, and Trump’s asshole-ism some more. “Paved the Rose Garden, put in a concrete slab.” At least I think the numbers were humorous, as I couldn’t hear them very well over the sound of no one paying any attention. I knowthey were numerous, at one point writing in my notebook haplessly, “two dozen acts, or three”? And at another, Emily Dickinson came to mind: “This is the hour of lead.”

No room for a complete list of the politicians and journalists who spent a Whole Saturday Night doing absolutely nothing but taking all of this in, but here are some of the ones I personally laid eyes on, aside from my friend Margaret: Rahm Emanuel, CNN’s Wolf Blitzer and Jake Tapper and Kasie Hunt, MS NOW’s Eugene Daniels, NBC’s Andrea Mitchell and Kelly O’Donnell, USA Today’s Susan Page, the Chicago Sun-Times’ Lynn Sweet, PBS’s Judy Woodruff and Amy Walter, NPR’s Mara Liasson and Tamara Keith and historian Douglas Brinkley.

And of course there were the main speakers—Pritzker, who delivered humor remarks for the Democrats, and Arkansas Governor Sarah Sanders, who hammed it up for the Republicans. Speaking of ham, Pritzker’s opening line was, “For those of you who chose the kosher beef option, here I am.” And added, “I’m the guy who put ‘gov’ in ‘Wegovy.’” (Word is, Pritzker hired some Daily Show writers to help with his remarks.) Of his potential presidential aspirations, Pritzker also said he was “one hundred percent focused on the people of Illinois.” But then added, “That’s not just me talking. That’s also a 2006 quote from Barack Obama.”

Pritzker sounded heartfelt as he made the obligatory noises in favor of journalism and the First Amendment, crediting several specific Chicago news organizations who reported on ICE overreaches in Chicago. 

Sanders, less so. She got off some good lines and left me liking her six percent more than the zero percent I liked her going in. “Singe, don’t burn,” she repeated. “Singe is the color of my smoke eye.” She also noted that she was the daughter of an Arkansas governor. “Mike Huckabee, not Bill Clinton,” she said. “He checked.”

But her Sincerity Signals, while lyrically written, amounted to little. She urged the audience to “take a break from looking down at our phones—and frankly, down on one another—” and instead “up at God,” and so forth. My writing hand refused to be more precise at that point. These are the last notes I took, before the nightcaps.

***

One element that was missing was a representative from the Trump administration, several of whose cabinet members declined invitations. “Without the Administration there the dinner felt aimless,” Another Speechwriter Friend observed in hindsight. “Like a roast where the guest of honor hasn’t shown up and the guests are trying to make a go of it without them.”

“You’ll remember what George W. Bush said to Michelle Obama after Trump’s first inaugural. ‘That was some weird shit,’” the Washington Speechwriter Friend texted me and Another Speechwriter Friend on Sunday morning as I sat writing this in a bar at Reagan National Airport. “Well, the Gridiron is some weird shit … but in the best way. And hopefully you’ll agree that the event is anachronistic … self-indulgent … and utterly fucking ridiculous. Yet at the same time leave thinking: You know what, maybe we should keep having this event every year. And maybe even we should have a little hope that there are some things, including institutions and constitutional rights, that will outlast the clown show of our government.”

That doesn’t contradict how I came away feeling, but it doesn’t capture it, quite. On this night I saw these journalists and politicians for what they surely are, at bottom: Working stiffs like you and me. Lives of their own, families of their own, needs of their own—for salads and main courses and desserts and wine (could we get a little more wine at this table?), and entertainment and most of all, occasional physical proof that they really exist and that others like them exist too and hope that all that existence is making some kind of difference, for the good. People, just like us.

Anyway, as it turned out, I got off the best line of the night, as far as I’m concerned—I, and the Uber driver I cracked up when we saw a woman crossing 14th Street on a very warm evening, wearing a thick fur stole. Without even glancing at the notecard in my pocket, I said, “She’s not cold. She just hates ferrets.”