An Oral History of Donald Trump’s Almost-Run for President in 2000
In late 1999, Donald Trump spent time and money exploring the self-evidently absurd notion that a shady real estate developer with a side hustle in self-help books could win the White House. With former professional wrestler Jesse Ventura occupying the governor’s mansion in Minnesota, there was strong whiff of populism in the air. To Trump it smelled like opportunity — at least for publicity if not for power.
Spurred on by longtime consigliere and former Nixon loyalist Roger Stone, he examined pursuing the nomination of the Reform Party, which Ventura had also recently joined. The Reform Party had emerged out of Ross Perot’s two presidential runs, in 1992 and 1996. Though Perot had never been a threat to win, he put up remarkable numbers — 19 percent and 8 percent of the vote, respectively — for an independent candidate, especially one as loopy and erratic as he proved to be. By the time the 2000 election rolled around, the party could offer to anyone who secured its nomination $12 million in federal matching funds and ballot access in nearly every state.
Trump, still more than a decade away from adopting snarling nationalism and right-wing conspiracy theorizing as his political brand, was a comfortable fit for the Reform Party, which at that moment saw itself as a vehicle for the Forgotten Center. The party intended to focus on trade and the economy while remaining agnostic on social and cultural issues.
Trump’s exploration efforts were, of course, highly visible. Op-eds were written, speeches given, Reform Party delegates courted. A core group of a dozen or more advisers and consultants were involved. But as Trump was testing the waters, right-wing firebrand Pat Buchanan and his supporters were taking advantage of the Reform Party’s low barrier to entry by becoming party delegates themselves. (Stone, a longtime Bush opponent, had encouraged Pat Buchanan to take a look at it, but had sided with Trump once the real-estate developer declared his interest.) Soon Perot’s party had undergone a hostile takeover by the Buchanan brigade, which changed the party’s orientation and made it all about fighting the culture war.
Ironically enough, the Buchanan campaign is now seen as an ideological precursor to Trump’s in 2016. But, at the time, the columnist’s seizure of the party derailed Trump’s flirtation with high office.
Here is how those who worked with Trump to explore the possibility of a Reform Party bid remember it.
Roger Stone, Trump adviser and right-wing operative: Donald was unimpressed with the candidacies of Bush and Gore. And it is important to recognize that because Ross Perot had run so strongly [in 1996] that the party had federal recognition. Therefore the nominee was entitled to a very large check, which was $38 million [Editor: It was actually a little more than $12 million.] So somebody would have the opportunity to run for the presidency on OPM: other people’s money.
Minnesota governor Jesse Ventura salutes naval officers he invited to his inaugural after taking the oath of office Photo: Craig Lassig/AFP/Getty Images
Jesse Ventura, former governor of Minnesota and professional wrestler: Donald Trump wanted to meet with me. He saw what I did in Minnesota [winning the governorship without major party support]. I was the hottest thing in American politics. I never thought he would pull the trigger. He talked about running for president all the time. He was my friend, absolutely. I knew him from Wrestlemania. But talk is cheap.
Russ Verney, Ross Perot political adviser and 1999 Reform Party chairman: In November of 1999, I was in New England for Thanksgiving — I was living in Texas, but I was in New England at the time, and I was invited by Reform Party activists in New York and Jack Essenberg, who was chairman of the Independence Party in New York, which was the state branch of the Reform Party to stop in on my way back and meet with Donald Trump. It was in his office at Trump Tower. It was a general discussion. It was more on the lens of what it would take if he wanted to run as opposed to was he going to run. It appeared to me that it was information gathering on his behalf, what the process was. It is an expensive proposition. We were on the ballot in a number of states but you still needed $10 million just for the petition drive. Jack Essenberg was there. Roger Stone was there. President Trump was very friendly, very warm. He asked a lot of questions. We ate sandwiches. I’d say the whole thing took maybe 45 minutes.
Phil Madsen, digital director for Ventura, and, briefly, for Trump: I never knew much about Donald Trump prior to this. I didn’t do a lot of research on him either. To me he was just some rich guy from New York. He wasn’t somebody I knew about or thought about or saw on TV that often. I didn’t see the need to do a lot of research on him. Keep in mind there was all of this interest in third-party politics around the country and Jesse Ventura was the star of the show. Donald Trump was coming to us.
Pat Choate, 1996 Ross Perot running mate and 2000 Reform Party chairman: I strongly discouraged him from getting involved with the Reform Party. I was the interim chairman. We had Pat Buchanan and a couple of other people looking at it. We were trying to get conservative Republicans to be involved. Trump sent Roger Stone to some event and talked to some of the people in the party. Basically I said we really don’t want Trump involved with us. He was just a hustler, just an egomaniac. And I think events have proved me right on that point.
Paul Hale, California Reform Party chairman: The Reform Party was a powerful experiment in government because we had to start from the ground up. We weren’t professionals. We were laypeople. So we had to build a platform, create all of our own committees. Our main theme was fiscal responsibility. The major parties were completely corrupt. We wanted to be totally ethical, do everything as straightforwardly as possible.
Dave Shiflett, co-author of Trump’s 2000 campaign book, The America We Deserve: I was a part of this ghost-writing writers group in Washington, D.C. Roger Stone reached out. Nobody took this seriously. Trump was a guy on a lark. The only thing I knew about him was the “Best Sex I Ever Had” headline. He was developing his expertise at being center stage and this was a way to get some headlines.
Stone: Donald was friendly with Jesse Ventura from his days in Wrestlemania and he was friendly with Ross Perot because in a certain world all billionaires know other billionaires, and I think he was intrigued by the idea.
Choate: Ross Perot and I didn’t think he was a fit. Because of his morals. Because of his finances. Because of his constant hustle. Because of his egomania and his inability to work with other people. I really didn’t think he would have a shot at it. They may be both billionaires but there is a zillion-dollar difference between Ross Perot and Donald Trump. For one thing, Ross Perot is a real billionaire. For another thing he made it on his own.
Dean Barkley, former Ventura aide: I heard a little item on NPR that Donald Trump was coming to Minneapolis and that he was going to ask me to run his presidential campaign. I hadn’t heard anything about it. So that was quite a surprise. Then a couple of weeks later Donald Trump flew out on the Trump plane. And that’s how I met Donald Trump. At the penthouse suite at the Northland Inn in Brooklyn Park, Minnesota. I didn’t think he was serious. I thought he was doing it for the publicity.
Stone: We formed an exploratory committee, built a database of those who would be delegates to the convention, started figuring out how to get Donald’s name on the ballot in states where there would be primaries, and figured out some campaign-style trips. He never became a formal candidate and made it clear he was just exploring. We released a tax plan that would have increased rates on the super-wealthy, which would include Trump himself, put out a book called The America We Deserve. Donald positioned himself essentially as a fiscal conservative but more of a social progressive, which fit the Reform Party closely.
Barkley: We encouraged him to do it. We told him that the problem was Perot was still a factor and wanted to quash anyone else. So not only would you have to quash Perot in the background you would have to make peace with him. Perot didn’t want to give up control of the party.
Madsen: I was deeply involved with Jesse Ventura, and one day I got a call from Roger Stone. He flew out and we met him at the Twin Cities airport. He told us that Trump was feeling out a presidential run. That intrigued us greatly because we had just made history with Ventura. Our dream was to start a national third party and Ventura was the star of the show at that time. We were socially moderate and fiscally conservative. We were the moderate middle. That is how we talked about ourselves at the time.
Barkley: We met for a couple of hours. He and Roger and a few other people, they were taking notes and picking our brains and asking us how did we win, and I politely said I wasn’t sure he was serious and I didn’t want to leave the Ventura administration on a lark. I didn’t say it was a lark to them but I did say that if he was serious he should let me know. I didn’t know what Donald Trump stood for. He seemed more interested in being a celebrity. I just kind of wrote it off as a publicity stunt.
Madsen: I met with him a couple of times. A small group met with him in his hotel suite in the Twin Cities. Melania was there, Roger Stone, and there were maybe six of us Reform Party people. Trump said almost nothing. He listened as people talked. I was a little embarrassed to be in the room. The other five people were just falling all over themselves to get on his side and to be a part of a presidential campaign. They were praising Trump and complimenting him. They just gushed over the guy. I was thinking, “People, he has heard all of this before. What are you trying to do. He’s Donald Trump. People talk this way to him all the time!” It was awful to watch. I felt really uncomfortable in that room.
Choate: I was party chairman so I was neutral. Except Donald Trump. I really didn’t want Donald Trump.
Pat Buchanan makes his way through reporters, cameras, and supporters in New Hampshire in 1999, after announcing he will seek the GOP’s nomination for president in the year 2000 election. Photo: Brian Snyder/Getty Images
Shiflett: It was him versus Pat Buchanan and Trump was a different guy than he is now. He was fairly politically progressive. Buchanan had come out with a book that said that the concentration camps didn’t kill as many people as everyone thought or something. Trump did an excellent op-ed on Buchanan that I have to admit I wrote every word of, it was a real teeth-rattler. Which is funny because now everybody says Donald is Buchanan.
Stone: Pat Buchanan came along and he was a fabulous foil. Donald accused him of having a love affair with Adolf Hitler. Donald is extremely competitive, and he read something that Pat had said, and Donald knew how to make news. Engaging Pat Buchanan got him an enormous amount of coverage. It wasn’t personal. It was opportunity.
Shiflett: If he puts out a book, it is going to sell well. He is a carnival barker. He can move product. And so Stone calls me and tells me Donald is thinking of running for president and wants a book that tells America what his priorities would be. We knew he wasn’t going to be president. There was a slightly carnival aspect to it all. Some interviewer called Stone for a story about the book and asked what other books had Donald read. So Stone called me and I said, “Tell ’em he likes Dostoevsky. See how that flies. That would add some gravitas to the soup.”
Madsen: Trump flew to Minnesota, he went to the Capitol and met with Ventura. They did this joint press conference. It was a media circus. And then Trump gave a speech to a bunch of local chambers of commerce. I introduced Trump at the meeting. I almost got into serious trouble because I was too long-winded in my remarks. The airport near Mar-a-Lago was going to close and if Trump missed that he would have had to stay in Minnesota for the night. I was going to be in deep doo-doo.
Shiflett: For some reason people who are very good at making money cannot write. I don’t know how that is. It’s not that high of a skill but they just can’t be bothered to do it. People say Donald Trump doesn’t read books. And that is absolutely true. Roger called me and said Trump wanted to write a book about what he would do if he were president. I said, “Well, this is going to be my first published piece of fiction.”
Ventura: If I had been running for president that year, I would have won. I would have won as an independent. I was the red-hot one. I didn’t run because I always thought you should finish the job the voters elected you to. But I would have won. You know how I know? In the year 2000, I flew into New York. It was the middle of the night. There was a construction worker fixing the streets in Manhattan. My window was open and we stopped at the light and I’m sitting in the back of the car and he stops working and looks over at me and says, “The wrong governor is running for president.” This was midnight. In New York City. It would have been me, not Donald.
Shiflett: I got off the elevator at Trump Tower, and I am just this hick writer from Virginia and there are these beautiful women just all over the place. They looked like they had been cooked up in a laboratory. They were just flawless beauties. I think Trump owned a modeling agency at the time. And Roger was there, and Donald, and I just took out a legal pad and we sketched out a couple of chapters. He just said what was on his mind. It was a one-afternoon thing. We just started going back and forth and I wrote it all out. I am a hack writer. And hack writers can stretch a word out of nothing.
Verney: I was invited to meet with him in Florida with a bunch of Reform Party members, and then a couple of us were invited to be Trump’s guests at Mar-a-Lago. It was a wonderful weekend. The place is just gorgeous, fantastic, everything about it is five star, including the restaurant. I was there with my wife, and Jack Essenberg and his wife were there, and here we are looking at this five-star restaurant menu and Trump comes over to our table and says, “On the way down here I called the chef, I gave him my mother’s recipe for meatloaf, and you have to try it.” So here I am at a five-star restaurant and I have to eat the meatloaf. And let me tell you I am glad I did. It was fantastic.
Stone: We had a reception in Florida with all of the Reform Party national committee members. How serious he was looking at this is a reasonable question. If you asked him today he would say Roger was more interested in it than I was. I think he loved the attention. He loved the platform. I think in the end he was less interested in running than I was in seeing him run. He saw the obstacles. Just getting on the ballot in all fifty states was going to be multi-million-dollar exercise.
Madsen: He flew some of us Ventura people down to Miami to accompany him on what was sort of like a campaign trip. He wanted to see how he was going to be received by the people who supported Ross Perot. We didn’t get to a Trump club. We were kind of hoping we might, but he met with a bunch of Reform Party people at a hotel somewhere. Then we all rode to Little Havana, where Trump was going to give a big speech to a bunch of Bay of Pigs Cuban veterans. It was intoxicating. He was the star of the show. To watch all of that unfold and be exposed to these historical figures and all. The Cubans were delighted to have someone of Trump’s stature pay attention to them. Stone was orchestrating the whole thing, all of it for Trump’s benefit.
Verney: There were a good number of Reform Party people who came to Florida for a meet-and-greet. I think he wanted to see what it would take and what kind of support he could tap into. My understanding was that Mr. Trump would have had to sell his casino in order to have the liquidity to run. And in the end he didn’t want to or couldn’t sell his casino and just didn’t have the cash.
Shiflett: The book was knocked out pretty fast. It just took a couple of months. I remember the first draft I sent in I did a get a call from Trump’s office and he had an assistant named Norma Foerderer, who was this very formidable woman, she had these eyes that could just burn right through you, and she called me and said you need to come up here. So I took a day trip to New York and went into her office and she said, “This needs to be toned down a bit. We don’t want Donald to look too strident.” I thought I captured his mood pretty well but okay, we can run it through the machine again and tone it down. She was very concerned that Trump not come off as some kind of ranter. And I was thinking, that is how he talks! He is a bombastic person. And also, I was thinking, why did you fly me up here? You could have just told me this over the phone.
How Trump's Speaking Style Has Changed Over The Years
Stone: He was enthusiastic about the publicity. He was enthusiastic about the adulation. It doesn’t mean he was was ultimately going to become a candidate. I tried to persuade him. I told him that he could be nominated, that Bush and Gore were turkeys, that there is grassroots enthusiasm for him inside the party, that this is the big leagues. In retrospect I was probably buying my own spin.
Shiflett: At the time he was this jet-setter. He wasn’t really famous for anything. He wanted me to put in the book that he knew Puff Daddy and Muhammad Ali. He told me Oprah would be a fantastic running mate and I should put that in there. I was like, “Okay, Donald.” At the time she was more famous than he was. I don’t think she would be interested in working for him. But it was like, “Okay, we will be sure to look her up and let her know that she is under consideration.”
Stone: At one point he floated Oprah Winfrey as his running mate. Now why did he do that? Well, I tell you it got us on the cover of both The Daily News and The Post. She was a national figure like him. She was friendly with him, and the idea of an independent black woman on a ticket with Donald Trump was a pretty attractive, pretty special idea. And we learned through all of this that the single most important quality for a candidate with Donald’s baggage was that everybody knew who Donald Trump was. He was already a national figure.
Hale: A bunch of us representatives from the Reform Party, we had a meeting with Trump. He rented a room in the Beverly Hills Hotel. It was a very nice affair. The thing is, though, we were grassroots, and I didn’t get the impression he represented the grassroots. He was billionaire. There was nothing unpleasant about him. He was a very nice man. I didn’t get the chance to talk to him though.
Stone: We went to Los Angeles, and stayed at the Hermitage Hotel in Beverly Hills. He had an event on the roof for Reform Party members and then we did a tour of the Simon Wiesenthal Center. I do remember him turning to Marvin Hier and saying, “Rabbi, this is a very valuable piece of real estate. What does this go for a square foot?”
Shiflett: His main concern when we did the book was terrorism. The reason was that he had an uncle who taught at MIT and he told Donald that it would soon be possible to make a bomb inside a suitcase that would flatten all of Manhattan. That got Trump’s attention. Among other things it would ruin the real-estate market there. And he was on to North Korea, which was interesting because nobody was onto North Korea. And the other thing was he was very much into single-payer health insurance. I remember that he wanted me to include that he didn’t like the Kim family of North Korea and he wanted me to put up-front that he was outraged by the murder of Matthew Shepard.
Madsen: Stone came out to Minnesota a couple of times. We were at some event, I don’t really remember what, and there were a couple of women from New York who worked in Trump Tower. In what capacity I don’t know. I remember them at this event getting a phone call or getting a note —somehow news coming to them that Trump and Melania had split up. I was shocked. They were very nice to each other. He would hold the door open for her, she would hand him a napkin if he dropped his. They seemed like a couple that got along quite nicely. And the next time Trump came to Minnesota Melania wasn’t with him.
Verney: Mr. Trump mentioned the Melania situation when we were at his club in Florida. He was clearly very hurt by it. He missed her very much. That came across in all of our discussions. He was very much in love, according to him, and missed her tremendously and wanted to what he could to get the relationship back to where it was.
Madsen: Stone hired me as the Internet guy. Put me on the payroll for a few weeks. I didn’t really do anything. Stone had his own people but he wanted me involved because of the Ventura connection. I did almost nothing. There wasn’t much work to be done.
Shiflett: After the book came out Roger sent me a card and said he found the smallest font possible for my name on the cover of the book. And he did! You can barely see me. But I got paid on time and got paid well. It was more money than this hack writer had ever gotten before. I knew he wasn’t going to run and nothing was going to come of it, but it is the sworn duty of hack writers to relieve rich people of their money whenever they can.
Stone: In the end he correctly realized that you had to be a Republican or a Democrat to make a serious run for the presidency. He would have won the nomination but he would have handed the presidency to Al Gore. But the most important thing to recognize is the extraordinary amount of publicity this generated. Because he is Donald Trump. Because he interested. Because he is provocative. The idea of a guy proposing a tax plan in which he would pay more but the national debt would be erased? That’s pretty provocative.
Madsen: In Minnesota, we [Ventura people] decided to break with the national Reform Party. It had become too much about Perot. And if we left, the Reform Party was going to fall apart. I remember telling Roger on the phone what we were doing and he said, “Well, that’s the end of that.” And they dropped out basically the next day.
Donald Trump outside the Federal Courthouse in Newark with Roger Stone, the director of Trump’s presidential exploratory committee, for the swearing-in of Trump’s sister as a federal appeals court judge in 1999. Photo: Daniel Hulshizer/AP/REX/Shutterstock
A few days later, Donald Trump sat down for an interview with Matt Lauer and announced he was out. “I’ve made my decision. I’m not going to be running. The Party is, as you know, self-destructing. Jesse has left, and that’s a problem. And so I will not be running.”
Asked by Lauer what he had taken away from the whole experience, Trump said, “I’ve learned the life of a politician. You know the other night, I was sitting at Mar-a-Lago in Palm Beach, Florida, watching television, and I was watching Gore on a freezing evening knocking on a door, saying, `Hi, I’m the vice president, I’d love your vote.’ He’s freezing. And I’m watching McCain, and I’m watching Bush, and they were all working so hard. And I said, `You know, it’s not such an easy life they have,’ as I’m sitting, you know, in 75-degree weather.”
But he quickly added he was interested in running again, only this time as either a Democrat or a Republican — and that if he did, he would come back on Lauer’s show to announce it.
Stone: The kicker to all of this is that after he withdrew it was too late to take his name off the ballot in California and Michigan. And he won the primary of both of those states.
Where are they now?
Paul Hale is a bus driver in the outer reaches of the San Francisco Bay Area, a career he came to after performing as a rodeo DJ under the name “Kicking Cowboy.”
Dave Shiflett is a self-proclaimed hack writer, living in rural Virginia, where he is working on a screenplay centered around Ronald Reagan, Sun Myung Moon, and Leon Klinghoffer.
Pat Choate has written several books and runs a small policy project devoted to restoring manufacturing jobs.
Dean Barkley served a brief stint in the U.S. Senate following the death of Paul Wellstone, and is now a lawyer in private practice in Bloomington, Minnesota.
Jesse Ventura hosts a television show on the Kremlin-backed RT America called The World According to Jesse and has suggested he will run for president in 2020.
Phil Madsen left politics, became a trucker and now runs a gym in Florida.
Russ Verney runs Project Veritas, the James O’Keefe led outfit that uses undercover videos to attack the liberal media.
Roger Stone remains an outside adviser to Donald Trump. He has expressed belief that he could be indicted by Robert Mueller. He is about to come out with a book attacking Bob Woodward.
