When Trump Was My Guest
Recollections of a long-time television producer
“No, no, no, put him through… he’s a good guy.”
Did Donald Trump really think I was that stupid? A self-proclaimed billionaire businessman who doesn’t even have a computer on his desk certainly understood speakerphones. He controlled the fact that I would hear him say “no, no, no, put him through, he’s a good guy.” (We had never met, nor spoken at that point.) No doubt it was a “trick” he employed in the hopes of making me, the caller, think he likes me, so I will in turn like him.
The reason for the phone call was for me to pre-interview Donald in advance of his first guest appearance on “Late Night with Conan O’Brien” the following day, December 10, 1997. From seeing Donald several times on David Letterman’s show, I knew his absurd persona made good television. He was a press-obsessed rich guy who would withstand searing ridicule and keep the appearance of geniality by forcing a smile, while rarely seeming to get the jokes at his expense. In our call, I hoped to find some potentially funny areas of conversation for his appearance on the show.
“Hello… I can hear you,” I said, pointedly not addressing him as “Mister Trump” as instructed. I knew he abhorred when people call him “Donald,” but thought if I had said, “Hello… Donald, I can hear you” the call might end immediately. So I just avoided it completely. If Walter Cronkite wouldn’t allow me to call him “Mister Cronkite,” I certainly wasn’t about to call Donald “Mister.”
“Hello?” I said again.
“Listen,” he yelled into the speakerphone, “I’m in the middle of a very important meeting, so make it good and make it fast.” I wanted to hang up. Nothing good would come of the call. It would not be a back and forth conversation, but a browbeating one-sided monologue with no other sounds during the call that indicated anyone else was in a “very important meeting” with him. Donald dominated our brief 12- to 15-minute pre-interview primarily boasting that he was now worth several billion dollars thanks to New York’s hot real estate market, while briefly plugging his other business ventures. In thinking, “how can I make a billionaire bragging about his wealth entertaining for a late night comedy show,” it occurred to me, “How much money does someone who claims to be a multi-billionaire carry around in his pocket?” Whether $10,000 or $10, I was sure my boss, the host Conan O’Brien, could make it funny. I didn’t tell Donald that the question would arise in the interview.
In front of 210 people in Conan’s live studio audience, Conan asked, “How much money do you have on you right now? How much money? What’s in your pocket?” Donald responded, “Lemme see, there is something in the pocket” and then reached down and pulled out a condom, held it up, then returned it to his pocket. Conan said, “Lemme see that! What is it?” and reached across Donald’s body. Donald pulled it out, held it over his head and said, “Safe sex everybody!” The audience reaction was a collective gasp, along with some hooting and laughter, but the impulsive reveal must not have been received as he had assumed it would. I became aware of that fact moments later when the interview was over and Donald walked off the set towards the exit. As soon as he and I stepped out into the hall beside the studio, Donald turned towards me, pointed and yelled, “Who the fuck does he think he is, reaching into another man’s pocket? I’ll never do this fucking show again” and stormed out. True to his word, Donald only appeared on the show seven more times.
Billionaires aren’t a natural fit for late night comedy shows, but politicians can be. John McCain, Bob Dole and Al Franken were great guests thanks to their senses of humor, comedic timing and sharp instincts. As a guest, Donald was nothing like the generous Bob Dole, who would call weeks ahead of his appearances pitching jokes he’d come up with to potentially share on the show. I remember once answering my phone in the middle of the workday and hearing, “Bob Dole here. Just wanted to run some jokes by you.” And for the next few minutes, he read off one and two line jokes that were hit and miss, with a few home runs. His comedic brain was so fast that at one point I didn’t realize he’d finished telling his joke and there was silence. I said, “Is that it?” He said, “Yeah… you couldn’t even give me a courtesy chuckle on that one?” I said, “I’m sorry Senator I didn’t realize you’d finished telling the joke.” He said, “I guess I won’t be doing that one on the show.” I laughed harder at Bob Dole’s reaction to the reception to his bad joke than anything Donald has ever said in an attempt to be funny.
Donald never came with jokes or funny ideas, but once the cameras were on he seemed willing to accept being made fun of to his face in exchange for national television exposure. He was unique in that regardless of the questions asked or the subjects raised on the pre-interview, Donald would answer a question he wanted to answer. If asked about Trump Water, he might clumsily pivot and declare “The Apprentice” was the №1 show on television. (It wasn’t.). “It’s number one…” he would say repeatedly on our pre-interviews, “and you better make sure I hear that tonight on the show. Okaaaaay? You understand? We are on the same network, riiiiight?”
The truth was I’d always found Donald’s lack of self-awareness fascinating to observe. I never missed an episode of his reality television show “The Apprentice.” Yes, I worked at NBC, the network that aired the show, but I really loved watching “The Apprentice.” My favorite moments were when contestants would be “rewarded” for winning a challenge with a visit to see Donald’s actual apartment in Trump Tower. I would giggle watching the contestants’ faces as Donald led them into the gaudiest golden foyer outside Versailles. “What do you think?” He would ask the bewildered contestants. And they would somehow gain their composure to say something like “oh my god,” as one might when witnessing a fiery car crash.
When Donald returned to “Conan” during “The Apprentice” days, I pulled aside Jim Dowd, the NBC publicist assigned to Donald, and asked, “So how’d you convince him to come back?” He said, “What happened last time?” As I told him about the condom display, he said, “Jesus… why? Why would he do that?” I said, “Because he’s Donald Trump, Jim! He’s a moron and he proved it when he pulled out a condom on network television.” Jim defended his charge and said, “Look, at least I got him to come back.” That he did, and Donald returned again and again to the show. At the time Jim was new to Trump world, but Donald seemed to really like him and within a few years, Jim left NBC and formed his own PR shop that had Donald as his biggest client.
I produced Donald eight times for his appearances on “Late Night with Conan O’Brien” between 1997 and 2008, during which he hyped Trump University, Trump shirts and neckties, even Trump ringtones. Once in 2005, I’d planned for discussion of then newly launched Trump Vodka, figuring there could be some laughs to be had if Donald were to talk about how it’s the world’s finest super-premium vodka, yet he claims to have never tasted alcohol. However, when I mentioned that Conan might bring up the newly-launched Trump Vodka on the show, Donald said, “I don’t wanna talk about that. I do it for charity. My brother Fred was a very bad alcoholic, died young. It’s for charity. Come on, let’s talk about something else.” It was oddly touching to hear that this hustler was showing restraint and even further that he was doing something for charity in the name of his dead brother. Of course, despite saying so on national television, there’s no evidence Donald ever gave even $1 to any charity from the proceeds of his Trump Vodka before the product’s trademark was reportedly abandoned less than 2 years after its launch. So much for the product’s slogan, “Success Distilled.”
Donald may never imagined that at some point in the future, scores of investigative journalists would look into his many dubious claims, whether about the charities who were said to have benefited from him, the source of his wealth or, as we learned later, the woman he paid off. Nor could many who have spent time with him over the years have ever imagined him as President of the United States. I certainly didn’t. In fact, over the years when people learned about what my job entailed (attempting to make celebrities funny on television) I was often asked, “who is the best celebrity you’ve ever met?” or “who is the worst?” I would usually say, “I don’t know who the best or the worst is, but I can tell you who the dumbest is… Donald Trump.” I would tell the story of that first “no, no, no, put him through he’s a good guy” phone call, the condom incident, and Donald’s prolonged insistence that “The Apprentice” was the №1 show on television despite years of steadily declining ratings that told a very different story. The truth was that by the time Donald presided over his final season hosting “The Apprentice,” the show had about a quarter of its premiere season ratings.
I had so little regard for Donald that when, after flirting with the prospect for years, he officially announced his run for President, I was giddy. I told anyone who would listen, “This ‘run’ for President is going to ruin his life! The whole world is going to see what a vacuous liar he is and his world will crumble! He’ll be an even bigger laughingstock.”
Less than a month later, I saw the headline “Trump Attacks McCain: ‘I like people who weren’t captured” and felt deflated. Only a month after his entrance into the Presidential race, I assumed the five-time Vietnam War draft dodger would have to drop out and my prediction for the world learning the truth about him wouldn’t be coming after all. Wrong again.
I truly believe that Donald only ran for President to boost his brand, that he never actually expected that he would even be competitive in the race. I saw no evidence he had even the slightest hint of the intellect, curiosity, attention span or character required to be president, and figured that he just dreamed of the trappings of the office and to be seen as a winner. I assumed he would hire professionals to run the government if he beat the odds and won over Hillary Clinton.
As Inauguration Day 2017 approached and media reports indicated that Donald hadn’t yet bothered to fill a vast majority of the jobs open in the executive branch, I suddenly had a flash of memories from the mid 90s, shortly before I joined NBC. I was working as half of a two-man “bi-coastal” PR firm when I got a call from an executive recruiter out of Chicago. We spoke on the phone for a while and then a few weeks later, she called to say that she wanted to talk to me about a job opportunity I might be interested in. She was staying at the Plaza Hotel on Central Park South. When I called up to her room at the appointed time, she told me that we would be dining in the Edwardian Room and that my first test was getting us “the best table in the house” despite not having a reservation.
My pleading for the corner table were met with more than a little resistance by the hostess. Thereby I failed that first test, as noted by the executive recruiter upon her arrival at dinner. A few minutes later, Donald walked into the restaurant and took a seat at the corner table. Seeing the owner of the hotel at the best table in the house put me at ease for failing that first test.
As we ate dinner, I learned the job was a media relations position in the real estate industry. The executive recruiter spoke a bit about the generous pay, long hours and demands I’d be facing, but still hadn’t told me the name of the company. Finally after our dinner plates were cleared, the executive recruiter asked, “Are you ready to meet the client?” I said, “Absolutely. Will it be tomorrow?” She said, “No, now. Tonight. Here.” I looked over at the corner table and said, “Him? THAT’s the client?” She seemed a bit taken aback and said, “Yes, it’s the Trump Organization.” I said, “Oh no. I wish you had told me it was HIM.” She got defensive and said, “I don’t understand your tone. The Trump Organization is one of the most successful real estate companies in New York.” I said, “But you live in Chicago. If you lived here and saw him in the gossip columns every day about what models he’s dating and who he’s fighting with, you’d know he was a buffoon. He’s a joke.” The executive recruiter grew more frustrated with each syllable I uttered. I said, “I don’t think it’s a good idea for you to introduce me because there’s absolutely no chance I’d ever go to work for HIM.” I never heard from that executive recruiter again, and in fact I left the world of PR for a job in television a few months after that dinner. Then in my first six months producing guests for Conan, I finally met Donald when he appeared on the show and I was assigned to produce him.
After taking that trip down memory lane about the would-be job with the Trump Organization I refused to even meet Donald for, I remembered Jim Dowd, Donald’s PR guy through his days on “The Appprentice.” I thought, “What ever happened to Jim Dowd?” So I did a Google search on him. The first article that appeared was a transcript from PBS’ “Front Line” from September 2016.
In the transcript, Jim offered observations and anecdotes about his time with Donald, especially his obsession with ratings and his insistence the show was №1 despite publically available rankings that put the show at number 72. At one point, he related a conversation where Donald asked, “Jimmy, would you like to be my (white house) press secretary?” I thought, “Why wasn’t Jim on the campaign, never mind in the conversation about the job of Press Secretary.” When I returned to the Google search, the second entry made my heart sink. It was a news article about Jim Dowd, 42, who died just days before the “Front Line” special aired. I have no idea what caused Jim’s tragic death at only 42 years old, but am crushed by the thought of his three young children losing their dad. I also realized that Jim’s death means there is one less person who knows the true pathology of pre-Presidential Donald up close and personal.
Donald was inaugurated as the 45th President of the United States on January 20, 2017. As the inauguration proceeded, I somehow felt a small sense of gratitude to have formed such a poor impression of him decades ago, thanks to all the items Donald placed about himself in the gossip columns of the New York tabloids, his laughable appearances on Letterman and more, and my own perception of his deceitful character. I also felt a sense of complicity for whatever role I may have played in helping normalize Donald in his improbable ascendancy to chief perpetrator of the most tragic chapter in American political history.
About the author:
Daniel Ferguson was a producer for Conan O’Brien for over 21 years from 1997–2018 and was recognized with eight Emmy Award nominations.
