The problem with Donald Trump’s jokes is that they’re not funny

When first he sought the Republican nomination and then the presidency, Donald Trump’s use of humour was the standout – if not “stand-up” — feature of his campaign. Casual, crude, and often very cruel, his humour nevertheless forged a connection with that cross-section of voters who were tired of the sunshine and lollipop rhetoric of American politics.

Trump was the antidote to the age of Hope, of Obama-style oratory, and a certain worthiness that had settled over Washington. Trump echoed the militant strains of online debate, channelling the same brand of hatred though material he could always mitigate by claiming it was humour. “Just a joke, folks” he’d say, his arms wide and accommodating, as if a man with such a big white grin could mean any of the savage things he was heard saying.

Humour explained why sections of the media (CNN in particular) routinely failed to treat him seriously, confusing the entertainment value of his campaign rallies for what they were actually achieving in motivating the Republican base. It explained his provocative yet effective use of the demeaning nicknames he gave to his rival candidates. Too many journalists treated his idiosyncrasies lightly, as if they had no merit, yet soon they too proved incapable of talking about Marco Rubio without mentioning “Little Marco”. Ted Cruz routinely became “Lyin’ Ted” and no put-down was more damning and ultimately destructive than that of “Low-energy Jeb”. If Jeb Bush ever thinks of running for office, he’ll have to start by finding a way of shaking it off.

We now know, of course, that Trump’s use of humour is not quite as simple as people once presumed. We learned this that hard way. His harshest critics routinely condemned him for things for which he might well have been innocent. Yet, at other times, he was perhaps excused by some when his words or actions were ambiguous enough to warrant doubt.

It still remains unclear if he was really making a joke about menstruation when he spoke about Megyn Kelly having blood coming from her “whatever” since he’d also use the blood imagery when talking about Chris Wallace.

What is now more certain, however, is that Trump’s humour is rarely innocent. It masks and obscures at the same time as it reveals his deepest preoccupations – his motivations and fears.

This was nowhere more evident than during the last weeks of the election, in October 2016, when Trump attended the Al Smith dinner. An annual charity event held in New York to raise money for Catholic charities around the city, it was the last time the two candidates would appear together, and tradition dictated that they gave a speech in which they told self-deprecating jokes about themselves and gently poked fun at their rivals. Except, this time, Trump wasn’t going to abide by tradition.

To this day, it’s hard to understand why Trump did what he did. Perhaps he looked over his prepared remarks and thought they would fall flat. As well as believing himself the smartest guy in the room, he also seems to think himself the funniest. Certainly, what he read out felt like a mix of professionally written material and lines he’d added himself. The latter were typical of the red meat he would routinely feed to rally crowds. Only this time, his jokes found no receptive audience. “We’ve learned so much from WikiLeaks,” he sniped. “For example, Hillary believes that it is vital to deceive the people by having one public policy and a totally different policy in private.”

You’re right if you noted that it’s not a joke. There’s no setup and no punchline. It’s just an insult, delivered at a celebrity gala, with the victim sitting just a few feet away. It’s why 2016’s Al Smith dinner is so memorable and why, at last year’s event, Paul Ryan alluded to dealing with an “abrasive New Yorker with a loud mouth” (though the twist to his joke was that he was referring to Chuck Schumer). In any case, back in 2016, Trump lost the room, with many attendees booing his remarks and many of those sitting on the dais looking uncomfortable. The sight of the two candidates refusing to shake hands summed up the entire election and the deep animosity between the two sides. Without a doubt, it was Trump’s least effective performance and, at the time, spoke of a candidate who was so sure he would lose the election, that he simply didn’t care. Throwing punches from the ropes, he didn’t mind where they landed, clean or dirty.

One might have hoped that Trump would have learned something from that night but it happened again, just this weekend, when Trump attended the annual Gridiron Dinner. In fairness, it sounds like his scripted jokes were better than those that peppered the Al Smith dinner. “We were late tonight because Jared could not get through security,” is not bad. Nor was his putdown: “I was very excited to receive this invitation and ruin your evening in person. That’s why I accepted.”

The problem is that Trump rarely sticks to his scripts or, at least, seems to insist on writing some of his own material. Prepared self-deprecating humour again gave way to quips that were cruel and unnecessary. One “joke” about Maxine Waters sounded very much like stock-Trump. “How about that one?” he is reported to have said. “Maxine Waters, ‘He must be impeached!’ That’s all she knows how to say […] And then I say — I get in trouble for this — ‘She has to immediately take an IQ test.’ And people go crazy.”

The thing is: if you want to understand what Trump really feels about a subject, look to his ad-libbed comments (especially those thrown onto Twitter in the middle of the night). He obsesses over Russia and constantly seeks to validate his victory as if subconsciously suspecting that his presidency is illegitimate. If his hostility towards Hillary has abated somewhat, the same is not true of Obama. It’s a loathing that, at times, seems to consume him. These are the topics that spontaneously well up from his psyche, that stewing cauldron of paranoia, and that would be unsettling if we had not come to expect it from this President. What also happened this weekend, however, was something new…

Speaking to Republican donors, Trump made a few comments about China’s President Xi who has just made a grab for power that would see him rule indefinitely. “He’s now president for life. President for life” said Trump. “No, he’s great. And look, he was able to do that. I think it’s great. Maybe we’ll have to give that a shot some day.”

White House officials will again brush aside these comments as mere “jokes” but make no mistake about the significance of what the President said. Despite Republican denials, the U.S. has spent the past year facing up to a real crisis of public confidence in its electoral system. Beyond the questions of Russian hacking is a failure of infrastructure that has not been solved since the problem of “hanging chads” in 2000. Too many states are reliant on antiquated machines and are apparently unwilling to back it up with a traditional paper-based system that would allow for proper accounting. America is also facing challenges to the gerrymandering that has been shaping elections across states for decades. Cases for Wisconsin and Maryland are shortly due to go to the U.S. Supreme Court, with Pennsylvania’s supreme court already ruling against the Republican gerrymandering that had resulted in some staggeringly outlandish boundaries that determined the outcome of the past three congressional elections. Slot Trump’s “joke” into that context and it suddenly seems less like a joke and more like one of the undercurrents of this administration.

Trump’s admiration for authoritarian leaders is already well known but this goes even further: proposing for the first time that America would be ruled best if it could be ruled longest by a permanent president. The audience’s cheers that accompanied this remark should chill anybody who fears that America’s standards of democracy have already been undermined by this president. Trump’s humour achieves more than what Freud called “the liberation of the absurd”. It amounts to the liberation of the unconscionable and does not sound very much like a joke at all.