Trump listened, flattered political leaders, tested how much pressure potential new allies and enemies could withstand, and received input from his inner circle. Five months after western New York Republican activists approached him about a gubernatorial run, he was ready to announce his decision.
On March 5, 2014, the same day Cox flew down to meet with Trump at Mar-a-Lago, Astorino declared his candidacy for governor. Trump’s attorney Michael Cohen brushed off the announcement: “Only Donald Trump has the ability to win the gubernatorial race.”1 When Astorino appeared at a rally in Syracuse two days later, Onondaga County GOP chairman Tom Dadey, a Trump loyalist, did not show up.
Trump toggled between state and national politics. He made a third visit to the Conservative Political Action Conference in National Harbor, Maryland, on March 6. In an 18-minute speech, Trump dinged Rubio on immigration,2 rambled about his 2013 trip to Moscow for the Miss Universe pageant and the fact that Russian president Vladimir Putin had sent him an unnamed present, and bragged about renovating his hotel in Washington.3
Sam Nunberg: His speech wasn’t well received at CPAC in 2014. It didn’t do well in the straw poll. He had to hone his message. Ben Carson [won].4 Plus, we didn’t pay as opposed to other people who pay to win it. It’s pretty meaningless. On the other hand, what it did show was even when we were doing well in the polls, Carson was doing well, and part of it was his appeal that he wasn’t a politician. Americans love the notion of electing a citizen president. They love the notion of electing a CEO president.
When CNBC’s list of U.S. business leaders came out on March 10 and Trump wasn’t on it, he tweeted in frustration, “The #CNBC 25 poll is a joke. I was in 9th place and taken off. (Politics?) No wonder @CNBC ratings are going down the tubes” and “Other worthy people were taken off the @CNBC list as well. Stupid poll should be canceled—no credibility.” Trump complained privately to TV executives, and Michael Cohen called CNBC and threatened to sue the network over the ranking, saying the station was “ignoring the will of the people.” The problem was that the internet poll was only one component of compiling the list, and a panel of experts decided not to include Trump in the final list.
The next day, Trump was back at the Onondaga County GOP dinner speaking about the state’s high taxes, the advantages of carrying a gun, that he’s not “a big global warming person,” and the greatness of Syracuse’s basketball coach.6
Then, on March 14, he tweeted his decision: “While I won’t be running for Governor of New York State, a race I would have won, I have much bigger plans in mind-stay tuned, will happen!”7
He said he would have run if the party wasn’t so disorganized—the same reason he gave when he stopped exploring the Reform Party nomination in 2000. “I have clearly stated that if the New York State Republican Party is able to unify, I would run for Governor and win,” he tweeted. “They can’t unify-SAD!”
It appeared to those who didn’t follow Trump’s political machinations closely that once again the real estate mogul turned celebrity pitchman had faked his interest in public office. “Here’s a shocker: Trump will not run,” the New York Daily News tartly headlined its brief news item.8
Not everyone had given up. Carl Paladino made one last desperate push. Trump promised to speak at his anti–SAFE Act rally in Albany on April 1, 2014, in favor of gun rights. Paladino hoped he could convince Trump to change his mind if he saw how many conservatives wanted to hear his message.
Even though Paladino would not succeed, the trip would offer Trump a fresh, ground-level view of potential Trump voters and confirmation that he didn’t need to alter his persona to mobilize them.
Nick Langworthy: We talked within 10 minutes of the tweet going out. He apologized, but he had to get the word out and make the decision official.
Michael Caputo: Trump gave it so much time, and he was so responsive and open about the process that after he said no, I could not imagine any way I could talk him out of it. He had heard everything. He took input from everyone. He squeezed every fact from every data point from every resource and then made his decision.
Carl Paladino: I called him the day before the gun rally, and I said, “Don, wear jeans and a flannel shirt.” He said, “I don’t have jeans and a flannel shirt.” I said, “Well, can you get jeans and a flannel shirt anyway? You could start a new line of clothing.” I mean, what the fuck? “There’s going to be 10,000 people there, and you want to fit in with them. You don’t want to come in a suit.” He said, “But the suit is my uniform. That’s how everybody knows me. I’ll think about it.” I go to pick him up at Albany Airport and he gets off the plane. He’s got his suit on. He said, “How do you like my jeans and flannel shirt?” I said, “You’re a prick.”
Sam Nunberg: It was a mistake to continue to do this stuff. It was a mistake to associate himself with Paladino.
Carl Paladino: In the car on the way to the event I asked him, would he give me the authority to speak to Astorino and offer Astorino the lieutenant governorship? I would explain to Astorino that you’re going to run for president, for at least a year you’d be running the show, but afterward, Astorino would be running the show. He’d be an incumbent running the next time out, and he’d get the name recognition that he didn’t have right now.
Roger Stone: Carl fervently wanted him to run for governor and kept telling me that he would, and I kept telling Carl he would not in my opinion. But those guys do have a bond.
David DiPietro: We got on the stage. He introduced Carl. Carl got a big ovation. There were probably two, three thousand people there.
John Haggerty, Republican political consultant: It’s the angry Tea Party–esque person who feels like their American values are being taken away.
David Laska: Cities in western New York have more in common with Cleveland and Cincinnati than they do with Manhattan. Their concern is that jobs have left and home prices are underwater. They need industry. That’s not the same economic pressure you have downstate. It’s a completely different economic agenda.
Carl Paladino: He’s standing in front of thousands of people in jeans and flannel shirts. This was a novel thing for him.
Matt Wing: At that rally they had a doll of the governor, a figurine, and it was being lynched. We were paying attention to that rally, not because we were paying attention to Trump. Because Cuomo’s strategy was to paint his opposition as extreme conservatives who have to pay homage to the base of their party.
Joe Borelli: In my three years in Albany, I’ve never seen that many people on the lawn of the Capitol. The grass had to be repaired. There was a lot of “Don’t tread on me” signs. This was essentially the tail end of the Tea Party movement, and I don’t know of any other rally that President Trump ever attended like that prior to his running for president. Perhaps that put the idea in his head that if you get a motivated, issue-based group of people, you can whip them up and get them excited about making legislative changes.
Paladino spoke first, taunting Astorino (“Rob Astorino is a good man, but we need someone who is going to get elected”) before introducing Trump as the “next governor of New York State.” Trump spoke briefly about the Second Amendment and held up his pistol permit, drawing cheers. “You have the constitutional right to keep and bear arms. You have that right and they want to take it away. And they are taking it away, slowly but surely, they are taking it away.”9 Trump left the stage and minutes later buzzed over the crowd of about 3,000 people in a low flyover with his helicopter emblazoned with his name.
Carl Paladino: He gave a good speech. Very pro-gun. Talked about his son Donald Jr., an avid hunter and fisherman.
Joe Borelli: He’s a guy who’s a billionaire and makes no secret of that fact and lives his life ostentatiously to the point where he wants his life to be seen as ostentatious, and yet he’s identifying with people from lower-income counties in upstate New York, and he’s bonding with them over an issue that they’re both angry about.
Jessica Proud: We watched him take off in the helicopter. He wanted to make a big spectacle. People were yelling from the ground. It was lifting up. He didn’t brush the crowd but he did a little circle.
Carl Paladino: The black Trump helicopter with “Trump” written on the side of it. It was 400 or 500 feet up. They did a circle around the crowd. The crowd was cheering. Astorino speaks. I chase him into the parking lot. I call him aside. “I got to talk to you for a minute. You haven’t got a prayer,” I said. “Will you take the lieutenant governorship?” “No, Carl,” he said. “Ed Cox will raise all the money I need.” I said, “You’re listening to bullshit, man!” He doesn’t come up with a nickel because he can’t raise money from heavy donors. They don’t respect him, but he said no. I told Trump he said no, and that’s when Trump says, “Well, it’s over, Carl.”
Michael Caputo: When he decided to get out of it, Roger called me and said, “Are you done now?” I said, “I’m done.” He said, “Stop getting in my way.” I said, “I wasn’t trying to get in your way.” He said, “You almost fucked this up.”
Roger Stone: The conversation went like this: “Mike, you fucking asshole. Stop pushing this stupid idea, please?”
David DiPietro: Bill and I were the only ones with Trump to start. Even at the end we were pretty much it. Me and Bill took a lot of grief in Albany.* A lot of barbs from people. One Republican senator said he already cut a deal—with the governor. “We’re going to lay down,” he said. “Rob’s not going to get anything from anybody. He’s not going to win, so we’re not sticking our necks out.” When Astorino got the nomination, that summer of 2014 before the election, he came out to my district. They have a Wyoming County Fair. Rob Astorino walked through this little county fair with two people. I watched him and not one person came up to him. He would stop in the middle of the causeway and they would just walk by him. Nobody recognized him or knew who he was, even with his shirt on for governor.
Roger Stone: Astorino went on to run a very good race against Cuomo considering that he had no money. He got 40 percent of the vote, and he hit Cuomo very hard on the areas in which Cuomo is most vulnerable. He ran an amazingly good campaign, but Cuomo is very adept at turning off Republican money when he needs to.10
Nick Langworthy: The last time I probably spoke with Trump was shortly after Election Day 2014 to recap the elections. We weren’t successful in New York. He suggested what might have been. He said he probably made the right decision.
Sam Nunberg: Trump never really said anything bad about Cuomo, and he didn’t really want to attack Cuomo in case he didn’t run. I’d send him suggested tweets attacking Cuomo, and he didn’t want to do them. He said, “Why should I attack Cuomo now? Why have a bad relationship with him?”
Roger Stone: He’s not the kind of person who suddenly says to you, “Wow, you were right all along.” You have to respect his own thought process. I made my own arguments. Others made theirs. In the end, he did the right thing. He didn’t run—he ran for president instead, and he won. I’m not unhappy about any of it. He’s his own man. He makes his own decisions.
John Haggerty: The relationships that were established certainly helped him during the presidential primary race in New York. Carl Paladino, Caputo, Nojay, DiPietro, Langworthy: they were valuable during the presidential run because he wasn’t starting from scratch in New York.
Michael Caputo: When he finally called me about it, he said, “I’m not going to do the governor thing. I’m going to do the big thing.” I understood that to mean the presidency. He asked me to help him when he did the big thing, and he’d get back to me.
David DiPietro: I was the first elected official in the country to endorse him. Nicole Malliotakis used to jab me all the time. She was a Rubio person, and we would go back and forth.
Frank Morano: When Rubio dropped out, John Haggerty and Michael Caputo sent her a funeral-style bouquet with a ribbon saying, “In Memory of Your Beloved Candidate.”
Nicole Malliotakis: It was terrible. [Laughs.]
Ed Cox: I attended the Pennsylvania legislators lunch [in December 2015]. Trump came right up to me and thanked me profusely. His decision to skip the governor’s race and run straight for president, as Roger advised, was paying off, as he was then leading the field of Republican candidates.
Michael Caputo: I asked him one time while we were sitting around about how he would win. “You hate political consultants. You hate pollsters. You don’t like ad guys,” I said. “How are you going to win in the Republican primary?” He said, “I’m going to get in the race, and I’m going to say something outrageous, so newsworthy that I’m going to suck all the oxygen out of the room. And then when that story dies down, I’m going to do it again. And I’m going to do it again until every one of the other opponents dies off from lack of oxygen.” Lack of news coverage. Deny everyone else media coverage until they die on the vine. I laughed, saying, “Okay. You think that’s going to work?”
Carl Paladino later became New York co-chair of Trump’s presidential campaign, penning an open letter to New York legislators asking them to “join ‘Trump for President’ and try to preserve what’s left of your pathetic careers in government.”
That Trump eventually decided not to run for governor does not make his foray into state politics a failure or a waste. Along the way, many of those around him would reveal their strengths and weaknesses. Michael Cohen’s ambition showed itself, as did Nunberg’s steadfastness. Valuable new alliances would be forged.
The exercise kept Trump and those around him sharp.