'President Chaos': A cartoonist's collection of work from Donald Trump's presidency

The New York City media landscape of the “crazy Eighties” was populated by larger-than-life celebrities, all vying for their spot in the limelight in the daily tabloids.

Among the most prominent were Mayor Ed “How am I doing?” Koch; Leona Helmsley “Queen of Mean” hotel mogul; Andy Warhol, art influencer; and John Gotti, the “Dapper Don,” to name just a few.

But the one who seemed to get more daily print space than all the rest was the brash young real estate developer Donald J. Trump.

I first started doing editorial cartoons about him in 1986 when he was making his reputation as a self-made real estate titan who could get things done (even though he worked for his wealthy father, Fred Trump, a well-established builder). Trump fed an endless supply of publicity pieces to the tabloid world. Sometimes he’d pretend on the phone to be his own publicity agent. He’d play one journalist against another, one paper against another. The stories were not only about his wild real estate adventures but also about hurling insults at his enemies while bragging about his love life. He had an insatiable need for headlines and having his picture on the front page. But it wasn’t very long before Trump world started to fall apart. 

Bankruptcy and divorce went hand in hand. One day I would be drawing about the Trump Taj Mahal casino, Trump Plaza Hotel, Trump Airlines, the Trump Princess yacht being sold off at fire sale prices. The next day, it was his very public divorce from Ivana, his first wife, and his affair with Marla Maples, soon to be his second wife, whom he would get rid of for number three, Melania. 

The New York Post cover headline “Best Sex I Ever Had,” attributed to Maples and purportedly provided by Trump, was Donald at his narcissistic nadir. At least until he ran for president in 2016.

At the same time, he was starting to talk publicly about political and social issues in a way that sounded just the same as now. Immigration, trade, crime, and race. In 1989, he took out a full-page ad in all the papers calling for the reinstatement of the death penalty after the so-called Central Park Five were charged and convicted of the rape of a jogger in the park. It was a crime they didn’t commit, and they were fully exonerated. Trump has never apologized for his ads.

Trump made an abortive run for the presidency with the Reform Party in 1999 but pulled out due to internal party problems. Still, it was a pretty accurate dress rehearsal for what was to come later.

After Trump’s six separate bankruptcies, more than 4,000 legal disputes in various state and federal courts, continuing illegal tax write-offs, and his mountain of debt that the banks restructured because he was just too big a “star” to fail, he turned himself into a popular television personality with The Apprentice. But by then, I had moved on to other subjects.

It wasn’t till 2016 when I saw him coming down the elevator at Trump Tower to announce his candidacy that I had the gripping white-knuckle sinking feeling that he really could become president.

I felt an urgent need to again start doing editorial cartoons about Trump, but this time I had no place to publish them other than my own hardly seen Instagram account. 

It was soon after that I learned that Shaun Mullen, my former college roommate and former Philadelphia Daily News editor, had started a weekly hard-nosed, fiery blog, Kiko’s House, on the state of US politics. I got in touch with Shaun, and soon I was contributing a weekly cartoon to his blog, working with him just like at the University of Delaware weekly student paper where he was the demanding editor and I was the perpetually missing deadline cartoonist.

Almost all my editorial cartoon career has been for publications that are weekly or even monthly. On the one hand, you have the leisure and time to come up with ideas about many topics. However, the choice of subject is often governed by whether it has “legs,” meaning whether it’ll still be relevant a week from its publication. Of course, there is always the chance that events will pull the rug out from under you, and what you’ve done will be superseded by other events that would be by then totally wrong. Luckily, when those embarrassing circumstances arise, my reading public has been quite forgiving or maybe not even paying attention. I’ve always seemed to get a chance to do it again the following week.

For the next four years, Shaun wrote and I drew all about the Trump administration’s many lows, such as separating immigrant children from their families, toadying to dictators and undermining the country’s allies to impeachment, and the pandemic response. We were starting to get some notoriety for our work, and in our last phone call we discussed putting together a book. Sadly, Shaun died from natural causes not long after we spoke. As an army draftee, he covered the Vietnam War for the Stars and Stripes newspaper. He was buried with full military honors.

I carried on through the January 6 insurrection and into February 2020, but it just wasn’t the same, so I decided to stop doing new cartoons. It seemed that most everyone liked Joe Biden and that he would have a routine, uneventful presidency. And as for Trump, he was history.

Then about a year ago, I looked at the state of our politics, specifically Trump’s resurrection, and, like Dr. Frankenstein seeing his monster start to breathe, I shrieked, “It’s alive!”

How does a cartoonist respond to Donald Trump's political resurrection?

My first thought was to start doing new cartoons again, but that seemed a daunting task.

While I was considering what to do, Liora, my wife, asked, “What about those 400 cartoons you did during the Trump presidency? Is anybody ever going to see them again?” I replied, “Who’s going to be interested in all these obscure references to events from four years ago? These days, people can barely remember what they ate for breakfast.” She said, “Maybe you should explain them a bit and put them in order.” And that’s when the light bulb went on. 

Each cartoon, in chronological order, would be accompanied by a short, sourced explanation, relevant posts and citations, putting it in historical context. It would be a book specifically for those deluged by the endless news cycle who couldn’t remember what had happened or thought that somehow it was better back then. Also, for those who were young then and not paying attention to current events but were now new voters interested in what happened when Trump ruled supreme.

First, I eliminated cartoons that were about local subjects or even too obscure for me to understand. That got it down to about 250 drawings. Then I started researching. That was hard. All the information I needed was online. I had to read at least two or three articles to get the essence of the subject that I had been cartooning and write only a short summary. I was really getting bogged down. Luckily, a professor friend recommended one of her students who she thought would be a great research assistant. She was right. She understood immediately what I was looking for, and we worked entirely online, without having to meet. In just a few weeks, she helped dig up all the articles, posts, and citations that I needed.

Next, I worked with an old friend and editor whom I had worked with on several magazine projects. By this time, I had my title: President Chaos: Cartoons from Trump’s Four Years of Lies, Insults, and Madness. After looking over all the material, my friend said she would edit with a very sharp surgical pencil and left only cartoons that were specifically about incidents that emphasized his “lies, insults and madness.” In the end, we agreed to leave 90 cartoons. A lot of my favorites fell by the wayside, but I knew she had hit all the important points and made the book coherent and readable. 

At the same time, Liora was working with graphic artist Ruhama Shaulsky in Israel. Together, they did the design of the book and the transfer of the images and text into a high-quality press ready pdf. Now and then it was a bit difficult with the time difference between New York and Israel, but today images and text can be delivered within minutes with no loss of quality just about anywhere in the world.

I see this work as a historical document that will live to enlighten people about how fragile democracy is and how a divisive authoritarian leader like Trump can destroy it with “lies, insults, and madness.”■

The writer’s book, President Chaos: Cartoons from Trump’s Four Years of Lies, Insults, and Madness, is available in the US on Amazon as a paperback and Kindle Ebook. For more orders, contact richard@looselineproductions.com. In Israel, for paperback books, contact Ruhama Shaulsky, ruhamash09@gmail.com