In late December 2013, after Donald Trump had met with a number of Republicans to discuss a possible run for governor of New York, he received a memo from an attendee, a freshman assemblyman from upstate.
The four-page briefing outlined the challenges most first-time political candidates face, including “endless chicken dinners” and a high probability of a “loss of income from serving in government.”
But the document also had the particular interests of Trump in mind: It was titled “Springboards to the Presidency.”
Trump has a long history of musing about running for office, and then abandoning the idea. His flirtation with the 2014 race for governor was viewed then as another headline-grabbing stunt, much as his current presidential bid had been initially dismissed.
But unlike previous dalliances, Trump’s deliberation on whether to challenge Gov. Andrew M. Cuomo, a Democrat, would be far more than a public-relations trifle.
An examination by the New York Times of contemporaneous documents and emails, as well as interviews with people who met with Trump during that period, illustrates how he carefully weighed a run, measuring whether the Governor’s Office was a necessary steppingstone to his long-held goal: the White House. His calculations at the time run contrary to the seat-of-the-pants image he projects on the campaign trail, and offer a look at a formative stage of his presidential ambitions.
He discussed with state Republican leaders the idea of using the governorship as a platform to run for president, a situation in which he would serve for a year or so and be succeeded by his lieutenant governor.
Trump also foreshadowed themes that have surfaced on the campaign trail, giving a blunt assessment of what he felt was ailing New York State and the country: jobs going overseas, crushing taxes, restrictive gun laws.
During another meeting with state Republican leaders at Trump Tower in Manhattan, the conversation migrated to the nation’s future. Trump told them he did not think the country could withstand eight years of Hillary Clinton after eight years of President Obama, according to a document summarizing the meeting. Trump added that he wanted to “save the country” from debt and felt the political left was going to destroy the American work ethic.
“He made it clear he wanted to run for president,” said Daniel W. Isaacs, then the Republican Party chairman in Manhattan, who attended the meeting. “Our pitch was if he runs for governor and makes it, he would be the presumptive front-runner.”
For his supporters, the recruitment drive offered an unexpected look at Trump’s budding strategy to capture the White House, which he predicted he would begin in 2015. As such, they tailored their local pitch to his national ambitions, saying that his road to Washington almost certainly ran through Albany.
“The most common path to the presidency is through a governor’s office (19 out of 43) and the most common governor’s office to hold is New York (4 out of 19),” Assemblyman Bill Nojay, the freshman legislator who represents the Rochester area, wrote in the memo given to Trump and a small group of Republicans.
Trump ultimately opted not to run, in part because he was irked that party leaders would not clear a path to his nomination. But in hindsight, supporters said, the experience helped inform his presidential bid as a populist with little regard for conventional politics.
Trump confirmed in a statement that the state Republican Party’s inability to assure an uncontested race was a deal-breaker, though he played down his interest.
He said that “even then, what I really wanted to do was run for president, and obviously, now that I am the substantial front-runner, I made the right decision.”
‘Almost iconic figure’
Trump is no stranger to being the object of political speculation. He hinted at running in the 1988 and 2012 presidential races, and his name was also mentioned as a possible candidate for New York City mayor in 1989 and for governor in 2006.
Perhaps his most sustained effort before now, though, involved his establishing an exploratory committee for a possible run as a Reform Party candidate for president in 2000, when he suggested that Oprah Winfrey would be his vice president.
But when Trump declared his White House bid last year, this campaign was no fleeting thought.
In 2013, New York Republicans were casting about for a candidate to take on Cuomo, who had amassed more than $33 million by January 2014 for his re-election campaign and was widely expected to win a second term the following year.
David DiPietro, a Republican lawmaker from the Buffalo area, said he and Nojay were on the floor of the Assembly that June, lamenting the corruption in Albany, when they first hit on the idea of encouraging Trump to run for governor.
A few months later, Nojay put their thoughts down on paper.
“In many respects Trump is not considered a Republican – he is his brand, an almost iconic figure of Rockefellerian proportions,” Nojay wrote in October in a three-page memo, “2014 NY Governor Race Analysis,” which he sent to a small group of party members, including Edward F. Cox, the state’s party chairman and a son-in-law of President Richard M. Nixon.
The conditions for a Trump-for-governor bid, the analysis continued, were ideal. New York City was about to elect Bill de Blasio, its first “truly radical” mayor, whom the memo referred to as a Marxist who honeymooned in Havana. “By 2014 a pro-business, proven executive will be welcome to offset” a Mayor de Blasio, the memo said.
The memo was leaked to the New York Post, and Trump used Twitter to tell Nojay thanks, but no thanks.
Behind the scenes, another story was playing out. A member of Trump’s inner circle contacted Nojay and, in early November, he and DiPietro found themselves meeting Trump for the first time, at Trump Tower in a large conference room with floor-to-ceiling windows overlooking Central Park.
The meeting, scheduled for roughly 30 minutes, stretched beyond two hours.
Intrigued, Trump agreed to keep talking about a possible bid for governor. A larger meeting was convened in early December.
Path to White House
Joseph C. Borelli, a Republican councilman from Staten Island who was an assemblyman when he attended the meeting, said, “He read the political landscape better than anyone. He all but said he would enter the presidential race in the summer of 2015 and he would be first in the polls.”
Some of Trump’s advisers, including Roger Stone, a veteran political consultant, opposed the run for governor, arguing that Trump did not need Albany to serve as a prelude to his 2016 presidential bid. But as a sign of Trump’s interest, one of his top lieutenants contacted Michael R. Long, chairman of the state’s Conservative Party, to discuss the possibility of an endorsement and a crucial extra ballot line.
Long said he went to Trump Tower in December 2013, “under the pretense that Mr. Trump would be there.” Instead, Long experienced something even more surreal: He arrived at Trump’s office, only to realize that Trump was not there and he would be speaking to him by phone.
It was clear, Long said, that Trump was “up to speed” on New York issues, and that he had a real animus toward Cuomo. But Trump, unwilling to face competition for the nomination, told Long that one condition for his candidacy would be to get Rob Astorino, the Westchester County executive who was already planning to run, out of the race.
“I made it clear to him, that’s not how politics works,” Long said. “It isn’t us picking up a phone and telling a candidate, ‘You can’t run.’ ”
Around the same time, Trump reached out directly to Astorino, whom he knew for many years through his golf club in Briarcliff Manor in Westchester. When they met at Trump Tower, Astorino said he told Trump, “Look, my intention is to stay in.”
Eventually, Astorino recalled, he was asked (though he would not say by whom) to consider joining a “unity ticket” in which Trump would run for governor and Astorino for lieutenant governor. Astorino would become governor after Trump declared his presidential bid.
“I didn’t think that was fair to me, or the people, or the process,” said Astorino, who ended up losing to Cuomo.
In January 2014, a small number of political operatives met privately with Trump in his penthouse at Trump Tower. One participant, Ralph C. Lorigo, chairman of the Erie County Conservative Party, recalled that he brought the necessary papers for Trump to form an exploratory committee to run for governor, with a notary stamp in his pocket.
“He toyed with it back and forth,” Lorigo said. “But I couldn’t convince him.”
Trump and the group then took the elevator down to his corporate offices, where they huddled with a larger group of dozens of Republicans, including numerous county leaders, who hoped to enlist Trump.
Not long after these sessions, Cox, the state’s Republican Party chairman, began to voice his concerns of a Trump candidacy. At a meeting at the University Club in Manhattan, which was attended by the some of the same people who had just met with Trump, Cox said he told the group, “I am really concerned this is not something he wants to do.”
Trump’s supporters were livid. “Donald Trump didn’t run for governor because Ed Cox wouldn’t get out of the way,” said Michael Caputo, a Western New York political consultant who helped arrange several of the meetings.
Undeterred, Trump flew to Buffalo and Syracuse, where he headlined local party fundraisers. In New York City, at a February fundraising event, Isaacs unveiled a large blue and red sign that read “Trump For Governor.”
The crowd erupted in applause, and many attendees expected Trump would announce his candidacy that night.
He did not.
A few days later, Trump ended the speculation via Twitter: “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!”