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Secret weapon: meet the Canadian comedian who writes jokes for Trump

Doug Gamble wrote jokes for Reagan, Bush, and John McCain, among other Republican luminaries. Now he writes them for Trump.

In the Trump era, the line between politics and comedy is so blurred it’s easy to mistake one for the other. Last March, CNN ran an article titled “This may be the scariest thing Donald Trump has said as President.” At a private event, following the news President Xi Jinping of China had removed term limits, Trump quipped: “He’s now president for life,” adding, “Maybe we’ll have to give that a shot some day.”

The remark was taken literally by many reports, and denounced as a horrifying harbinger of Trump’s dictatorial designs.

Comedy writer Doug Gamble knew better.

The line wasn’t an off-the-cuff remark where Trump was actually considering making himself dictator; it was in fact an unused joke Gamble had scripted for the Gridiron Dinner – a well-known political roast that occurred the night before. A veteran of the White House Correspondents’ Dinner and other such satirical events, Gamble had been asked by Trump’s staff to submit jokes. (The White House did not respond to a request for comment).

Trump, of course, is known for being boastful, and Gamble played on that. The president began by saying: “My staff was concerned I couldn’t do self-deprecating humor. I told them not to worry, nobody does self-deprecating humor like I do.” And then came actual self-deprecating humor, which Gamble notes is perhaps the only time Trump’s done so. On meeting with North Korean dictator Kim Jong-un: “As far as the risk of dealing with a madman is concerned, that’s his problem, not mine.” Following the publication of the political exposé Fire and Fury, Trump had been painted in the press as a basket-case good for the asylum. But in humorously acknowledging his frenzy, Trump actually engaged in some smart role-reversal.

If politics is a funny business, the career path to it seldom passes through comedy. Not so in Doug Gamble’s case – but it would be quite the journey getting there, a journey that would take him from his native Canada to California and then to the White House, when he became master joke-writer to President Ronald Reagan.

His deft touch and political insight soon made him a household name, and gave him one of Washington DC’s most illustrious – and unusual – careers. He would go on to write for two more presidents, including Trump.

Gamble also helped Mitt Romney and other Republican presidential hopefuls, as he puts it good-naturedly, “lose.” Along the way, he worked with all the big names in the Republican Party – John McCain, Dick Cheney, Carly Fiorina, California Governors George Deukmejian and Pete Wilson – and business executives on Wall Street and Main Street alike.

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Cast your mind back to a time – another epoch really ­– when Americans didn’t get their news fed to them by social media algorithms but instead from watching the nightly news on TV. The images were grainy; there was no HD  and only a handful of channels. Life seemed simpler. Dan Rather told America what was going on, and America listened. Sure, like today, people vehemently disagreed with each other – but they did so using the same information. The ethos of Edward R Murrow, honest reporting and sober commentary, ruled. It had yet to be supplanted by “infotainment”; news wasn’t yet a spectator sport.

The year was 1984. Jedi ruled the galaxy, but Ronald Reagan led the free world. On 20 February, just like he did every night, Gamble tuned in to CBS Evening News.

President Reagan was running for re-election and had just given a speech in Waterloo, Iowa. The highlight: “If the big spenders get their way, they’ll charge everything on your taxpayer’s express card and, believe me, they never leave home without it.” That joke sounded awfully familiar to Gamble. It took him a moment to remember why, and then it came to him: he had written it.

Three months prior, a White House staffer had heard his work on the radio and rang him out of the blue. Would he be interested in writing jokes for the president? He had jumped at the chance, and sent in some samples, but he had heard nothing back. Accustomed to the peaks and troughs of false hope that is the life of a writer, he had moved on. “I couldn’t believe it!” Gamble tells me with glee when I meet him at his house in Carmel, California – an idyllic beach town out of an old Technicolor film. Three decades on, he has lost none of his wonder at the moment that changed his life.

The morning after he heard Reagan use his joke, Gamble received a call: the White House wanted more. The chief speechwriter Ben Elliott said why: “It’s not just humour for humour’s sake. Your humour makes a political point, and you share the same sense of humour as the president.”

And so it began: Doug Gamble became Ronald Reagan’s joke whiz and his secret weapon. For four years, Gamble provided the man known to Americans as the Great Communicator with the quips, puns, wisecracks and zingers that brought down his rivals and endeared him to the American people. But before scripting one-liners for the commander-in-chief, Gamble was just a Canadian kid who liked to make people laugh.

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Doug Gamble grew up in Ontario, Canada. As he puts it, “I had a knack for humor.” While his peers played hockey, Gamble wrote down little jokes and limericks on pieces of paper, giving them away to friends and family. If he elicited a smile, or better yet, laughter, Gamble knew he was onto something. “At a young age,” he reminisces, “I was searching for an audience.”

In childhood, he showed a creativity and writing speed to turn most professional scribblers green with envy. Once, when a babysitter looked after him and his siblings, he drafted a mock newspaper story chronicling the events of the evening – leaving it on the kitchen counter for his parents to enjoy on their return.

Gamble always looked at things differently from anyone else. Where others saw mundanity, he spotted ridicule and felt the need to report it. His mind, in fact, had a mind of his own. He describes it with a metaphor: “Picture a big trailer pulling a little car on the highway. Well, the ordinary person sees just that. But if you think differently, you go: ‘Isn’t it amazing how that little car can push that big RV?’”

To be a good comic, you must assume nothing and question everything. At age eight, Gamble was doing just that. Hearing about the 1952 US Presidential election between Eisenhower and Stevenson, he asked his mother: “What’s an election?” As she explained, Gamble remembers a eureka moment: “How interesting that two people compete in public for a job”, he thought. “Which means if you don’t get the job, then everybody knows!”

From then on, he never missed another American election, and started following Canadian politics too. What fascinated him about the democratic process was “the competition between two people, [ultimately] a competition of ideas.” You are only as good as what you say and how you say it. Gamble had already grasped the basic principles of the ancient art of rhetoric, as described by Aristotle. Policy may be science, but politics – the stuff of rhetoric – is oratory and theatre. To excel, the performer’s instinct is compulsory. So is knowing your audience. And just like for a Broadway show, boredom is the cardinal sin.

But while politics thrives on drama, comedy wasn’t usually in the politician’s tool box, at least not in the 1980s. That’s perhaps because, back then, comedy wasn’t really political. Gamble notes the iconic talk show host Johnny Carson made political jokes but “no one ever knew what his political leanings were.” Then came hip liberals Jon Stewart and Bill Maher, among the first to use sarcasm to influence public debate. In 2018, Gamble decries, Jimmy Kimmel and Stephen Colbert have turned “late night TV into anti-Republican hate fests.” He points to “funny conservatives like Mark Steyn, Evan Sayet and Dennis Miller,” but mainstream media, he laments, doesn’t hire their like.

Gamble began the 80s as a Sunday humour columnist for the Toronto Star, Canada’s largest newspaper. But politics still enthralled him. By then he had become a resolute Conservative, and cheered when the Liberal government of Pierre Trudeau was voted out of office the previous year. But to his dismay, only nine months later, Trudeau was re-elected or – as Gamble sees it – “resurrected.” In his acceptance speech, the prime minister exclaimed: “Welcome to the 1980s!” To Gamble that sounded ominous. “Not me, I’m out of here!” he remembers mulling – the scorn still in his voice. His wife at the time was American, and they decided to move to Los Angeles. But politics wasn’t the sole motivation; humour was in the mix too. Gamble had made a name for himself in Canada, and now wanted to try out his luck in the entertainment capital of the world. Could he become a joke writer for Hollywood’s top comedians – despite his political leanings?

Gamble and his wife arrived in the US at the time of Ronald Reagan’s stunning election victory. Gamble immediately became enamoured of the new president. What caught his attention – and moved him – was Reagan’s inaugural address in January 1981. To Gamble, “it was everything an immigrant like me wanted to hear.” Reagan exalted uniquely American motifs: the wind of freedom and the frontier spirit, the benefits of entrepreneurship and the gift of opportunity. Simply put, after a decade of nightmares that saw the Vietnam War, Watergate, recessions and runaway inflation, Gamble saw Reagan perform CPR on the old and dying ideal of the American Dream. In the speech’ conclusion, the president called on the people “to believe in ourselves and in our capacity to perform great deeds … After all, why shouldn’t we believe that? We are Americans.”

Although Gamble was still a Canadian citizen, he saw in himself the kind of American character Reagan was referring to. Eager to get ahead, he hung out at the Comedy Store on Sunset Boulevard, approaching star comedians with envelopes full of one-liners. His bravado paid off. Some of his jokes were purchased and performed by Joan Rivers, Phyllis Diller and Rodney Dangerfield. It wasn’t exactly a profitable business model, but it got him noticed. Enough for Gamble to become, two years later, a writer for legendary comic Bob Hope. Gamble had achieved his American Dream. With hard work and gumption, he’d made it to the top. But the American Dream has no curtain call, and Gamble – as Franklin Roosevelt and later Reagan liked to say – now had his “rendezvous with destiny.”

In 1983 Gamble, by now a committed Reaganite, felt the media unfairly blamed the president for every ill in America. So he decided to poke fun at liberal anchorman Dan Rather and drafted a mock news story, a habit he’d kept since childhood. At the time, Cabbage Patch Dolls were all the rage in America, so much so that with Christmas looming, stores were running out of merchandise. Gamble imagined Rather reporting on this shortage; The Onion before its time. The highlights: “What should the Reagan administration have done to make sure this critical shortage did not happen? Does the president’s inaction mean he is insensitive to the wishes of children at Christmastime? … And finally, is breaking the hearts of children at Christmas an impeachable offense?” In Canada, Gamble would have sent it to like-minded friends. But in LA, everyone was a Democrat. Gamble specifies however that his “politics were never a factor when selling jokes to comedians.” He may have been an outlier, a conservative in a mostly liberal industry, yet “all [people] cared about was whether what I submitted was funny.” But this time, his stuff was decidedly political. So he mailed it to conservative talk show host Paul Harvey, “hoping he would put it up on his bulletin board.”

A few days later, on 13 December 1983 – Gamble still remembers the date by heart – “Harvey closes the program by reading my entire piece!” But destiny had more in store. “Somebody at the White House heard it, liked it, tracked me down and said: ‘What do you think of writing for the president?’” Gamble was gobsmacked. “It would never have occurred to me to send humour to the White House.” Who has ever heard of political joke writing?

At the White House’s request, Gamble drafted material on spec. The jokes came easy. A trenchant observer of politics, he’d fumed for years at left-wing politicians, big government and tax-and-spend. Now was his chance to settle old scores using the sharpest of swords: wit. Gamble was finally doing Aristotelian rhetoric, the kind that had made him love politics as a child. Just a few months later he was hired to provide one-liners for Reagan’s re-election campaign. What was that like? “Working from California, I would receive a speech draft and go through it looking for opportunities to add jokes, make points. Other times, they would tell me the president has a speech here or there. So I would research the place and find jokes [targeted at the local audience].”

Although Gamble hadn’t yet met Reagan, the two were in sync. Gamble pitched to perfection, and Reagan knocked it out of the park. Then came Gamble’s triumph, at the apex of the 1984 campaign – perhaps the single greatest joke in American political history. It came on the night of the second debate, October 21. By his own assessment, Reagan had “flopped” in the preceding debate. Then aged 74, he’d appeared tired, called military uniforms “costumes” and mistakenly said “here in Washington” while the debate was in Louisville, Kentucky. He fell seven points in the polls, and the media was buzzing with the same question: was Reagan senile?

As Gamble points out, “it was the first time the age question was raised.” The Republicans were in panic mode. This could well lose them the election. What should be the president’s response? Curt Smith, then a speechwriter for the Reagan cabinet, remembers: “Every Tom, Dick and Harry was asked to submit suggestions and jokes.” But Reagan refused to look at them. He said he had a plan but wouldn’t tell anyone. Some thought him mad. The second debate came along, and journalist Henry Trewhitt quizzed the president: “You already are the oldest president in history. And some of your staff say you were tired after your most recent encounter with [Democratic candidate Walter] Mondale. I recall yet that President Kennedy had to go for days on end with very little sleep during the Cuban Missile Crisis. Is there any doubt in your mind that you would be able to function under those circumstances?”

Reagan appeared cool and focused, like the actor he had been. Then a nod. “Not at all. And I want you to know that also I will not make age an issue of this campaign.” The words were flowing, Reagan looked serious. “I am not going to exploit, for political purposes, my opponent’s youth and inexperience.” As if on cue, laughter erupted. His opponent, Walter Mondale, was 56 and had served as Vice-President. Hardly a novice. But even when faced with a joke that would go down in history as his political death-knell, Mondale couldn’t help giggling.

With one line, the president had neutralised the issue and reminded America he was the sheriff in town. All thanks to Gamble, who had devised the riposte – the verbal equivalent of a first-round knockout punch by Mike Tyson. Gamble explains, “That line was not written for the debate. I had turned it in two weeks earlier. When Reagan read it in a speech, he knew right away: it’s too good for a speech. The president metaphorically put it in his pocket, saved it for the debate and surprised everybody.”

What’s so impressive about this one-liner is it works on multiple levels. The combination of Gamble’s creativity and Reagan’s flair accomplishes more in a minute than armies of Ivy League consultants ever could in their lifetime. With this rhetorical pirouette, Reagan not only dismissed any doubt he was unfit for a second term, he also turned his Achilles’ Heel into a rabbit’s foot. Weakness became strength. By deploying humour, he instantly reframed the debate, going from defense to offense. Picture a boxing match. Reagan is in a corner of the ring, getting the life beaten out of him. But instead of punching back and attacking his opponent from the front – as a lesser politician would have – he slid to the side and let the other boxer punch away until he fell over.

Reagan succeeded precisely because he refuses to answer the question the way it was asked. Such is the sly nature – and genius – of the comic in politics. As Gamble puts it, “It’s a way to disarm criticism.” Sometimes it can even pre-empt it. Another line Gamble wrote for Reagan did just that: “I’ve given my aides instructions that if trouble breaks out in any of the world’s hot spots, they should wake me up immediately – even if I’m in a Cabinet meeting.”

Making light of oneself achieves something else needed of a campaigner: it radiates confidence. Gamble remarks, “If you’re comfortable in your own skin, you poke fun at yourself.” The same is true in romance. Warren Beatty, one of history’s foremost playboys, was a keen practitioner of self-deprecation, because he had so little to deprecate. And politics, of course, is a game of seduction. So when Reagan – a man who kept grace under pressure and boasted natural assurance – made fun of himself, it was charming. But Gamble warns that if, say, Richard Nixon – a notorious neurotic – had tried to use self-deprecating humor, no one would have bought it. “It would be phony, because people know that’s not what he’s really like!”

Political humor, however, is not just about asserting personality; it can also make abstract policies palatable to the general public. Gamble worked on Bob Dole’s 1996 campaign. One of the cornerstones of Dole’s project was tort reform. He wanted to keep lawyers from filing so many civil lawsuits on spurious – sometimes even ridiculous – grounds. Dole was giving a speech on the campaign trail and fell from the stage, hitting the ground. Gamble’s phone rang. It was Dole’s campaign manager: “We’ve got another event in an hour. We need to say something about this.”

Gamble explains this is called “rapid response.” Simply put: Unexpected things happen during campaigns and the candidate has to react immediately. Otherwise he appears stuffy or, worse, wooden. Gamble found a way to work tort reform into a one-liner, turning mishap into opportunity. He had Dole tell the crowd: “I guess you heard what happened to me earlier. I have to tell you. Before I even hit the ground, my phone rang. It was my lawyer saying he thinks we have a good case!”

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Although Gamble can trade in jokes, that’s not all he does. He refers to his work as “trying to make a point in a creative and memorable way.” He’s a maestro of the political aphorism, short statements filled with wisdom. In the 1988 election, for instance, he was called upon to provide material for George HW Bush’s acceptance speech at the Republican Convention. The goal was to present Bush as the rightful heir of Reagan, the president best suited to continue his legacy. Drawing inspiration from an old line by Roosevelt, Gamble wrote: “When you have to change horses mid-stream, doesn’t it make sense to switch to one who’s going the same way?” The Detroit News used that line as the reason they endorsed Bush. In her memoir What I Saw at the Revolution: A Political Life in the Reagan Era, speechwriter Peggy Noonan writes that: “Reagan told me that was the single best statement of what was at issue in the 1988 campaign.”

In the trade of politics, these “statements” are known as soundbites. They’re what people remember from a speech – and what get journalists buzzing. Gamble’s wordcraft has made the headlines, been played on endless loops on TV, and, with Trump, set social media afire.

How did Gamble survive so long – and thrive – in the cut-throat world of politics? Where others crashed and burnt, he always kept his cool. He shuns the spotlight and understands that, in politics, the place of the writer is in the wings, not centre-stage. It helps that he lives 3,000 miles away from the political circus, in picturesque Carmel, California. Like the first president he served, Gamble never sought to become a political insider, preferring the sun-drenched vistas of California to the gray landscapes of Washington. He’s in politics not for ego but because, just like Reagan, he’s a true believer.

When I tell people I’m writing about a man who injected humor into conservative politics, some wonder if that’s not to be deplored. Jokes distract from the issues and mislead the public. Politicians shouldn’t do humour because their decisions touch and often hurt millions. And it’s true, that’s no laughing matter. But should politics really just be about stating facts and arguing policy? Why can’t it also be an open-mic contest? John Cleese said it best: “Too many people confuse being serious with being solemn.” So does humor really debase politics? Is politics bound to be solemn and serious, meaning, to many of us, boring? Charles de Gaulle once quipped: “Politics is too serious to be left to the politicians.” John Kennedy Jr. went further: “Politics is too important to be left to the politicians.” Great politicians, luminaries from Franklin Roosevelt to John Kennedy and Reagan, all had the funny bone and the artist’s soul.

They knew – as Aristotle discovered, and as Gamble exemplifies – that politics is not policy. It’s about dreaming big and, yes, having a grand old time doing it. Without lyricism and wit, democracy dies and morphs into technocracy, serving only the powerful and interesting only the wonks.

By making politics entertaining and stimulating, Doug Gamble did American democracy a great service. By getting more people interested in them he helped make public affairs what they should be: the people’s business. But tell him that and he’ll laugh. Because although he takes politics seriously, he doesn’t take himself seriously. And that’s precisely the kind of people politics needs.

Theo Zenou is a writer who covers politics and culture, and develops shows for TV. He tweets @TheoZenou.

Theo Zenou is a writer who covers politics & culture and develops for TV. He tweets @TheoZenou