Trump was peeved at Romney and the Republican Party and more resolved than ever to run for president in the next cycle. He kept his political advisers employed and sought ways to stay in the national mix. But 2016 was still distant.
New York State Republicans had even more challenging problems than the national party. Democrat Andrew Cuomo had swamped Buffalo billionaire Carl Paladino, a Tea Party favorite, by a 40-point margin in the governor’s race in 2010. After legalizing gay marriage and capping property taxes, Governor Cuomo’s approval rating topped 70 percent in a 2012 Quinnipiac poll.1
But he infuriated Republicans after pushing gun-control measures, known as the SAFE Act, through the legislature in January without public hearings.2 And he vexed progressives when he dithered over allowing natural gas drilling known as fracking in the state’s Southern Tier.3 Still, his approval numbers stood at 62 percent in November 2013,4 and the campaign treasury was up to $28 million.5
It would take a monumental effort to match Cuomo’s war chest. Republicans, primarily clustered on Long Island and spread across rural swaths of upstate and western New York, had difficulty competing in statewide races. Westchester County Executive Rob Astorino, a former radio producer who won reelection in November 2013, wanted to try, and was encouraged by the state’s Republican Party chairman, Ed Cox, a descendant of prominent East Coast families, married to Richard Nixon’s eldest daughter.
Two western New York lawmakers had other ideas. David DiPietro, a former mayor of East Aurora who owned a dry-cleaning business, and Bill Nojay, a conservative talk radio host who would commit suicide two months before the 2016 election,6 won assembly seats in 2012 and were plotting how to shift the state party rightward.
In October 2013, DiPietro and Nojay brainstormed whom to draft for governor, but the list of conservatives who could bankroll their own campaigns was not a large one. By enticing Trump to seriously consider running, they wound up connecting him more closely to the kind of ground-level activists and disaffected voters who would prove crucial in his ultimate rise.
David DiPietro, Erie County state assemblyman: Bill Nojay had this radio show. I was the mayor in this little village. I was running for a state senate seat, and he put me on his show and we hit it off. He said, “You’re great on the radio.” We both ran for the State Assembly in 2012. I hadn’t seen Bill in about two years, he was totally off my radar screen. I got elected to the assembly in January 2013. I go up to the state capitol into my conference and there’s seven new members, and Bill’s one of them. We looked at each other and said, “What are you doing here?” He said, “I got elected.” I go, “So did I!”
In October 2013, Bill and I were at a SCOPE* banquet at Lucarelli’s in Lackawanna on Abbott Road, around the corner from my house. Afterward, we were sitting on the hood of my 2003 Ford Explorer at 10 o’clock talking about who to get to run for governor. We started going through names and debating if they had a chance, and we came up with Donald Trump. Both our eyes lit up. We thought he would be a great candidate, self-funded, highest name recognition of anyone in the country, would make it a marquee race. We had to decide how to get in front of him. I called a friend of mine, Mike Caputo, right there from the hood of the car and told him what we were interested in. He said he would call Roger Stone.
Michael Caputo, Republican consultant and former Carl Paladino campaign manager: DiPietro said that he and Nojay were having conversations, and they were looking for a Republican candidate who could beat Andrew Cuomo. One of the parameters included being able to self-fund a campaign. It would have to be someone in the business world who could raise or spend enough and somebody from the downstate New York City area because of the importance of that area in the electoral landscape of New York. We triangulated Trump. I called Roger Stone and Sam Nunberg. Roger told me that there would be no interest because Trump is shooting to run for president.
Sam Nunberg, Trump campaign adviser 2011–2015: I don’t think they took it seriously that he was going to run but they took him seriously because he was tweeting, he was on Fox News, and he was speaking out. He told me he was running that summer in 2013. He said, “Look, I think I’m going to run for president.”
Roger Stone, Trump adviser and political consultant: He didn’t have any interest in running for governor. I also thought the race would be, ironically, a more difficult one than the presidential race, but I agreed to help facilitate a meeting on the theory that these were friends he would need down the road if he ran for president. Frankly, the job was too small for him. He would hate living in Albany. This is the bluest of blue states. This is a state without a single conservative newspaper—I would argue the New York Post has a more populist editorial viewpoint. Andrew Cuomo is a very tough, very mean, extremely well-funded opponent.
Michael Caputo: Roger said, “He’ll tell you no but if you want a meeting, we can do it.” He said Trump was going to run for president and running for governor would ruin his ability to run for president.
Sam Nunberg: He would obviously win the Republican primary but it wasn’t realistic he would win as governor of New York. It’s a very unwinnable race for Republicans, and essentially he’d be a smarter, classier, more refined Carl Paladino, but he’d still be a Carl Paladino.
Carl Paladino, Republican New York gubernatorial candidate 2010: I’d met Roger Stone during my 2010 campaign. He knew me as a very honest, straight-up person who wasn’t afraid of anything. When I first got together with him in New York, he made it a point to take his shirt off and show me his tattoo, which is a face of Richard Nixon on his back, and I said, “Fucking cool, man,” and he said, “Cool? This is what it’s all about, man. You go all out when there’s a challenge.”
On October 12, 2013, Bill Nojay composed a memo titled “2014 NY Governor Race Analysis” explaining that Trump would be an attractive candidate because he doesn’t have to spend as much money to tell voters who he is and can pull voters regardless of party affiliation. “In many respects, Trump is not considered a Republican—he is his own brand, an almost iconic figure of Rockefellerian proportions,” the memo said.7 Nojay leaked it to the dean of the state capitol press corps, Fred Dicker.
Fred Dicker, New York Post Albany bureau chief: Nojay was a very smart guy, and he was close with Carl Paladino. Guys like Caputo or Stone had a financial interest in [a Trump campaign for governor], and Bill Nojay may have had a financial interest, but he also had a genuine belief, as did Carl Paladino. He laid out a scenario, which made some sense. It was certainly a possibility putting together disparate coalitions that would back Trump. There’s a downstate Republican Party and an upstate Republican Party. Downstate is dominated by Long Island Republicans. They tend to be affluent, may be better educated, but they’re New York City–oriented. They may be conservative on some social issues like abortion, but that’s about it. When it comes to spending, they’re no different than the Democrats, and they tend to favor restrictions, say on natural gas fracking, as the Democrats do. Whereas upstaters, much poorer, are focused on trying to get jobs. It’s almost a sine qua non that you’re a strong Second Amendment supporter in upstate, where gun clubs, recreational shooting, hunting, and self-protection are very important. It’s a fundamental divide. Trump is not a Manhattan Republican. In his policies, he’s much more like an upstate Republican than a New York City Republican.
The article got Trump’s attention. He called Dicker and said he was “very flattered” that Republicans wanted him, but it was “not something that I’ve ever even thought about.” Then, a few hours later, Trump called Dicker back and argued, “Taxes are way too high, and people are fleeing New York,” and “We should become the energy capital of the East.” And he called Cuomo’s father, former governor Mario Cuomo, “one of the worst governors in the history of the state … otherwise, I like [Andrew Cuomo] very much.”8
Three days later, Trump tweeted mixed messages. “Thanks for all of the great support but I just don’t see myself wanting to run for Governor of New York-I have something else in mind!” and “By the way, New York State MUST LOWER TAXES (and fast) and must start going after all of the ‘energy’ that lies just below our feet (now)!” He was referring to fracking.
The Cuomo campaign responded with a shrug, but the publication of the memo led to a sit-down. On November 13, 2013, DiPietro, Nojay, and Caputo flew from Buffalo to meet with Trump and his political team, including his lawyer Michael Cohen. Cohen, who lost a city council race in 2003 to Upper East Sider Eva Moskowitz, had his own political ambitions.9
David Bossie, Citizens United founder and political consultant: In November 2013, I called him up and said, “Mr. Trump, I’m going to do some big events in the first three states. I’m going to put together an event in New Hampshire for early next year, would you come?” And he immediately said yes, which made me think, “Hmm, he’s getting more serious.”
Matt Wing, Cuomo campaign aide: My take was always pretty much the same. There’s no way he’s running. He’s been the guy who cried “I’ll run for office” over and over, and he’s never actually done it. Donald Trump is notorious for not writing checks. We certainly didn’t take seriously any concept that he would actually self-fund in any seriously competitive way. We had $30 million at that point. Donald Trump, at the most, would maybe put a million dollars in. It’s all a sham. It’s all a show. When you make a big deal about the fact that you live in an apartment with a gold-plated toilet that means that, actually, you’re full of shit.
Sam Nunberg: We accepted the premise of the meeting. Trump would be happy people are talking about recruiting him for governor, which would then show he’s a solid candidate with the potential to run for president. I had [Manhattan Republican chairman] Dan Isaacs come.
Dan Isaacs, Manhattan Republican Party chairman 2011–2014: Rob Astorino had been an old friend of mine from my Young Republican days. Bill Nojay said, “We’re trying to convince Trump to run for governor, and would you join us?” I said, “Absolutely.”
David DiPietro: I’ll never forget in the cab all the way from JFK, which is about a half-hour ride to Trump Tower. Me, Mike [Caputo], and Bill [Nojay] are in the backseat, and we’re talking about why Trump was going to win. He connects with the average voter. They don’t know him as a political politician. They know him as a multibillionaire, from his casinos, and his USFL football team the New Jersey Generals. They know Donald Trump from everything but politics. When we get out of the car, the cab driver, who is Ukrainian, gets out and says, “I’d vote for him!” I looked at Bill and said, “That’s exactly what I’m talking about. The average voter likes this guy. That’s why he’s going to win the governor’s race.”
Sam Nunberg: Right before the meeting happened, we talked. Trump didn’t seem that enthusiastic about it. I explained to him who’s going to be in this meeting. He said, “Okay, fine, I’ll go.” Before he entered, Trump was thinking about it more. He started talking about the fiscal state of the state, Cuomo, and other Republicans who ran in the past like Mayor John Lindsay. He said it would be great if the state had a Republican governor.
Michael Caputo: I had been in Trump Tower before, but Dave and Nojay had not. In Buffalo we don’t have atriums seven stories high lined with Italian marble. We went up to a secured floor, got off, and we were met at the door by [Trump bodyguard] Keith Schiller, who signed us in with another security guy. They escorted us into a big conference room.
David DiPietro: They took us into the boardroom and they had a little luncheon set up for us. We were there about five minutes, and Trump came in with a couple of his people. We sat down and he said, “What do you got?”
Michael Caputo: I led the meeting, but then Trump put it into Q&A pretty quickly. We were warned by Stone that it was going to be a short meeting, that he was going to say no, and that he was going to ask a lot of questions. So we tried to give him encouraging answers, and it kept going on and on and on.
David DiPietro: Trump was taking notes and asking all sorts of questions about our analysis. Why are we going to win? What’s the strategy? How do you plan on getting the vote out? We wanted a campaign that wasn’t media heavy but was grassroots at the county level, and he seemed to like that. He asked, “How much will that cost?” We said, “About $5 million.” He said, “No problem.” He asked where we were going to put that money, and we went county by county, setting up the chairs and how to get the people registered. Our goal was to register 250,000 new voters. We would get the gun-owner list and go door-to-door.
Michael Caputo: Trump asked how this would hurt or help his run for the presidency and how much it would cost. He asked the actual chances of him winning. And he asked us about the State Republican Party chairman [Ed Cox], who he said he had a relationship with and if we thought he would be supportive. We knew that the state chairman was being very supportive of Westchester County Executive Rob Astorino, so we told him he would not likely be supportive, that Astorino was his man, and that he doesn’t react well when he’s challenged with his picks.
David DiPietro: He just said, “I’ll take care of Rob. I know him personally. I’ve supported Rob in the past. Rob’s come and visited me many times. I know him.” A couple of times during the meeting he would say, “Clear my schedule for now, clear my schedule,” when someone came in to get him.
Michael Caputo: Sam started being interested in it as well even though he was on the presidential beat. And Cohen got interested in it.
Sam Nunberg: I’m thinking this was all bullshit that he could win. He would not have got one fucking vote in New York City. He would’ve got 20 percent, 15 percent at the most, and Cuomo would’ve spent a lot of money. But all these people started telling him he could win. Flattery always works with him.
Michael Caputo: It was very clearly interesting to him. Nojay talked about how the governorship was a stairway to the presidency for so many men. That if you’re governor of New York, there’s nothing out of your reach politically. It was a contrast between going from businessman to president and from businessman to governor to president.
David DiPietro: He had been looking at politics but he had never cut his teeth on it. It’s one thing for someone who’s a doctor to say, “I’m going to run for politics.” It’s another thing to get out there and learn what it takes. “You flirted with the presidency,” we told him. “You’re the one guy that could buck history. No one’s ever been president of the United States as an ordinary citizen.” He said, “Really, is that true?”
Dan Isaacs: He’d be the presumptive front-runner for the GOP presidential nomination.
David DiPietro: After three and a half hours he goes, “Boys, I thought this was going to be a three-minute meeting and I was going to tell you thanks a lot but not interested. Let’s set up another meeting. I’m interested.”
Michael Caputo: The fact that he invited us back again was very exciting to all of us. He went from “I’m just not interested” to saying, “Okay, I’m open-minded.”
Sam Nunberg: Meeting’s over. We say goodbye to everyone, go upstairs, and he says, “So guys, what do you think?” He was excited about it and I said, “I think it’s a mistake, I don’t think you should do it, I don’t think it’s realistic.” Michael [Cohen] is very excited about it. Michael says, “You should do it.” Michael was thinking he was going to use this as a platform to try to run for mayor. Michael thought it was realistic that Trump could win. I said, “Cuomo’s a very strong candidate in the state. That’s the first issue. The second issue is it’s a very hard race for a Republican to win, and you’re very conservative.” I told Roger what was going on. Roger said, “This is a big mistake.”
David Bossie: He had people around him who were giving him bad advice, like Michael Cohen, who were telling him to think about running for governor of New York. And I thought, “That’s the dumbest thing I’ve ever heard.” You’d have to spend as much time and money and possibly work harder than running for president, with a greater chance to be president as opposed to getting elected governor of New York.
Sam Nunberg: Cohen has delusions of grandeur. He even mentioned trying to be Trump’s lieutenant governor. He met with Ed Cox sometime early 2014 and mentioned he was interested in running for mayor.
Hank Sheinkopf, New York political consultant: When I first met [Cohen], he wanted to run for city council. And then he wanted to run for state senate. And then in 2013 he wanted to run for mayor. I said, “Everybody who wants to run has got to have something to say. What are you going to say?” He said, “Well, Mr. Trump’s going to win the presidency and I’m going to be in position—” I said, “That’s okay. That means you might be able to get the money. But what are you going to say? What’s the message here?” I said, “You have to bring a check next time for one million dollars and we can talk.” He talked about other people that would be happy to work with him. I said, “Okay, me too. But come back with a check.” He ain’t been back with a check.
Roger Stone: Nojay said he had a revelation from Christ that if Trump ran, he would win governor. Generally speaking I prefer polling data to revelations. But it’s very hard to tell Donald Trump he can’t win something. He’s a winner by nature, and he doesn’t necessarily believe you.
Ed Cox: Roger Stone gave me a call early in the process. I always thought he was a political genius. He often sees things other people don’t see. He had called me and said, “Donald should run directly for the presidency.” Now clearly the way it was going is Trump thought he needed to have a stepping-stone to the presidency so he had to run for governor.
Trump asked Bossie for a poll about his prospects in a gubernatorial race. Trump’s interest perplexed Bossie, but he hired Kellyanne Conway, a pollster who advised Newt Gingrich on his 2012 campaign.10 Although the raw results of the December 2013 poll showed that Cuomo would beat Trump by 35 points, Conway’s summary spun it differently:
NY loves its celebrity politicians and families: the Kennedys, Moynihans, Buckleys, Clintons, and even the Cuomos. Donald Trump fits that (loose) bill, and he has the money and moxie to compete.… When offered a choice between offices, New Yorkers are more than twice as likely to urge Trump to run for Governor of New York (27%) than President of the United States (12%). A plurality a third option: run for neither.11
David Bossie: Kellyanne and her husband had owned an apartment in one of his buildings, but Kellyanne was my pollster, so when Trump was asking for recommendations I said yes, she should be somebody that he brings in to help him. I commissioned that. We did a two-night poll. One of the questions in the first night we asked [if he should run for governor]. And Trump asked me to change the question to whether he should run for governor or president for the second night.
Roger Stone: Trump was well aware of my opinion. He would say, “I can beat Cuomo. He’d be easy to beat. Everybody I know hates him. He’s done nothing as governor.” Donald seemed to believe that he would easily defeat Cuomo. David Bossie financed a poll and the poll did not show that, but I did think the poll results, at least in the executive summary, were somewhat manipulated to highlight a more favorable number and hide the more problematic numbers. He knew both [Bossie and Conway] at the time, and they both wanted him to run for governor. The problem of course was twofold: Trump always had this issue of people not believing he was really running for anything. Another professed interest in running for governor would only exacerbate that if he didn’t really run. If he ran for governor and lost, it would preclude a run for president a few years later. It never made any sense to me.