one funny rule of presidential politics

A thing I think we must regrettably concede is – and please don’t unsubscribe, but – Donald Trump is funny. The unraveling of America should not be funny, and yet sometimes you can’t help but laugh. Which is part of how he got there in the first place.

Yes, Trump is mostly funny now in an old man declaring he’s very good at flagpoles kind of way, but he rose to power as an entertainer and insult comic. His rallies were raucous political carnivals built around his gleeful mockery of the staid establishment, and everyone was laughing along.

Even in 2024, after inciting a violent insurrection in the Capitol, Trump effectively leveraged humor – in hourslong podcasts where he detailed “the weave” and in slapstick stunts where he cosplayed a McDonald’s worker or garbageman – to short-circuit the Democratic portrayals of him as a fascist.

Or perhaps it’s the other way around: humor is an undervalued heuristic for political talent, encapsulating attributes like authenticity, relatability, charisma, and attention capital.

Either way, it’s a potent signal. In fact, the funnier candidate has arguably won every presidential election since 1980 except the aberrant COVID election of 2020.

In some of these elections, humor proved essential. In 1984, for example, Ronald Reagan successfully neutralized his biggest political vulnerability – his advanced age – with a famous debate quip that left both Mondale and the moderator in stitches.

Barack Obama – who introduced himself to America as “a skinny kid with a funny name” – similarly used self-deprecating humor to defang fearmongering about his identity. Do yourself a favor and watch the 2008 Al Smith Dinner; it was a genuine comedic masterpiece from both nominees. (John McCain was funny too; that race was really the only close call on the laughometer.)

Obama also excelled at making fun of politics-as-usual in a way that endeared him to the disaffected electorate – the same trick Trump used, albeit without the grievance-maxxing. My favorite example from 2008 was this bit about his biggest weakness:

Unfortunately, the post-Obama Democratic Party has suffered from a certain humorlessness, among other deficiencies. Indeed, I’ve taken to calling us the Democratic Book Club, because parties are fun.

But perhaps our humorlessness has been downstream of our leaderlessness. In lieu of a defining personality, the right-wing media machine has filled the void, defining us clip-by-clip, one ultra-leftist weirdo after the next. Perhaps we are only one charming leader away from a great brand cleansing and cultural resurgence.

To me, AOC, RAHM EMANUEL, GAVIN NEWSOM, and GRETCHEN WHITMER are the funniest contenders, and each in different ways. 

AOC’s humor is the most accessible and versatile. She’s best known for her pithy clapbacks, but it’s her Zohran-esque warmth and magnetism that allow her to connect, whether she’s politely disemboweling Elon Musk at a hearing, laughing off her haters on an IG story, or owning her idiosyncrasies, like having never seen The Godfather.

“Warmth and magnetism” is not a phrase you’ll hear applied to RAHM EMANUEL. The pint-sized pugilist is famous for his caustic one-liners – and undiscerning about his victims, be they allies, foes, staff, or press. “I think it's actually a stupid question,” he told Jonathan Martin on a recent episode of his food-forward podcast. “You’re not earning your pizza.”

NEWSOM’s 2025 rise to quasi-frontrunner status of course coincided with his embrace of cartoonish Trump mockery. There’s a ceiling to that schtick, and he seems to have hit it. But his quick wit and ability to laugh at himself may be the superpowers that allow The Great Gavini to escape his calculating image; watch the podcast he did with his sister if you don’t believe me.

Speaking of recent This Is Gavin Newsom guests… GRETCHEN WHITMER doesn’t seem like she’ll run in 2028, but she does seem like a damn good hang. Even Republican legislators enjoy knocking a few back with That Woman From Michigan. I mean, what’s not to love about a governor who pumps herself up before big public appearances with “It’s Shark Week, motherfucker!”

The old ‘beer test’ was surely designed with men in mind, but it’s Whitmer and AOC who earn the highest grades. The other obvious category fit is JB PRITZKER, who literally gifted the Pope a 4-pack of Chicago-brewed ales, and has won over many-a-reporter with his comedic banter at off-the-record dinners.

After that, you have PETE BUTTIGIEG, whose sense of humor has flourished in his fatherhood era, though he’s more cerebral than laugh-out-loud funny. I’d probably put RUBEN GALLEGO and ELISSA SLOTKIN in this next tier as well, and maybe JOSH SHAPIRO and WES MOORE. All of them at least understand jokes and can occasionally participate in them, which can’t be said for everyone in the field.

In a world where Democrats are seen as stilted, scripted, and self-serious – where authenticity is king and the bar for achieving it keeps rising – humor will be an invaluable 2028 commodity.