Alfred E. Smith Dinner Gag Writer on Clinton-Trump Roast: "The Rules Don't Apply"

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A humorist who has penned jokes for everyone from Michael Dukakis to Al Gore says the key to coming ahead in the Trump-Clinton comedy face-off is to "be self-deprecating."

It began in 1960, when two bitterly opposed presidential hopefuls — Richard Nixon and John F. Kennedy — stopped by to break bread and crack wise at each other's expense.

Ever since, the Alfred E. Smith Memorial Foundation Dinner has become a campaign tradition, a chance for candidates and voters to enjoy a brief reprieve from all the mudslinging for, well, even more mudslinging — only this time, it's meant to elicit laughs.

But that was before Donald Trump came along.

"The political playbook is thrown out the window," says Mark Katz, a veteran speechwriter who penned gags for several Democratic presidential candidates at the event, from Michael Dukakis in 1988 to Al Gore in 2000. "All the rules that usually apply don't apply."

Framed as good fun, the dinners serve a highly useful secondary function, acting as comedic Rorschach tests administered to the two figures vying for the most powerful job in the world.

"They really reveal things about you that are intentional and unintentional. Once a candidate showcases their humor, you learn a lot more about how their brain works," explains Katz, who now runs the Soundbite Institute, crafting witty speeches for politicians and high-powered executives.

A white-tie fundraiser benefiting needy children and held at the Waldorf-Astoria New York, the Alfred E. Smith Dinner is hosted by the city's Archbishop — currently Cardinal Timothy Dolan. At the table of honor, Dolan will be the only thing separating the Republican candidate from Democratic nominee Hillary Clinton — whom Trump snarled was a "nasty woman" just one day before.

God be with them.

The key to giving a winning performance at the dinner is to "be self-deprecating," says Katz. "Figure out the worst thing your opponent might say about you and find a way to say it about yourself." For Trump, who appears to have spent a lifetime erecting a wall between himself and humility, that could prove to be an insurmountable challenge. 

"When you hear these jokes, the thing to listen for is, what have they just conceded? What did they just elicit using humor that they couldn’t otherwise say? And I don’t think you’re going to hear a lot of concession or confession in Trump's humor," Katz says.

Clinton, too, arrives without her own set of potential pitfalls. Hit Trump too hard — as Seth Meyers and President Barack Obama learned at the infamous 2011 White House Correspondents Dinner — and her opponent could spin that humiliation into revenge-fueled resolve. 

Nor is Clinton particularly famous for self-abasement. But skipping the event "would be a critical misjudgment," Katz says, denying the candidate a prime opportunity to spoof her own foibles in front of the nation. (The dinner airs live on C-SPAN at 5:50 p.m. PT.)

"She would do well to move along that risk-reward ratio of conceding more in order to get louder and more meaningful laughs. It's credibility out of humor," he says.

It would be unwise to completely count out Trump, however, a man who has proven himself capable of landing an effective punchline — with a stress on the "punch."

"It seems very reminiscent of that Rat Pack sensibility and the cadences of it," Katz says of Trump's sense of humor, and cites one joke from the 1950s-era Las Vegas comedian Shecky Greene that sums to illustrate what he means.

"'People say all kinds of things about Frank Sinatra but he once saved my life," the joke goes. "I was once being beaten mercilessly by a gang of goons and Frank said, ‘That’s enough, boys.’"

"Whenever I hear Trump deliver a joke," Katz says, "I somehow reconnect to that joke."