Politics, recent

The Simple Secret of Trump’s Supreme Political Confidence: Old-Fashioned Fan Mail

Donald Trump knows how to demonize the privileged and other targeted segments of the electorate as a means to connect with the masses. The phrase “connect with the masses” has an elitist ring, but it describes his reach as well as his fan base. His years hosting The Apprentice made him a TV star; millions welcomed him into their homes every week and never retracted the invitation. It also characterizes Trump’s approach; the accessible appeal of a man who, despite his billions and iconic brand, can craft instant intimacy with 10,000 people in an arena, and multitudes more over the airwaves.

Trump flirted with a presidential bid over the years, teasing and threatening to run for the office, boasting to reporters and the public that he was certain to win if he did, while privately acknowledging the dizzying implausibility of finding success in the unfamiliar arena of politics.

Yet when he finally leaped into the race in 2015, it was no surprise to him that he met a warm reception—not from the press or the Republican Party, but from the citizens who attended his rallies. His events started out large, and became gargantuan. At first, fans who kept dog-eared copies of The Art of the Deal on the family bookshelf, or who watched Trump on The Apprentice every week, came out to see the famous businessperson. They were accompanied by the curious and the bored. Then the energy changed, and the venues expanded. “It’s a movement, folks,” Trump told his crowds triumphantly, and he was right.

Perhaps Trump had not predicted how smoothly he would ascend to the nomination, nor how swiftly he would dispatch his Republican rivals, but he had been convinced his people would show up in droves to join his movement. Part of his confidence came from a fingertip feel for the populist mood of the country, gleaned from his massive media consumption and his rollicking, bring-the-house-down speeches at events such as the annual Conservative Political Action Conference, or CPAC, a gathering of conservative activists from around the country. But part of his confidence came from the binders.

In the spring of 2011, I was invited to visit Trump Tower and meet with its eponymous owner. The billionaire had spoken at CPAC that February, and I was present to cover the meeting. A number of well-known conservatives and would-be presidential candidates appeared at the event. But when Trump took the stage, the room was packed to the gills with avid listeners, many of them young. The speech Trump gave— vilifying Beltway elites, career politicians, China, Mexico and illegal immigrants—would become familiar to cable news and YouTube viewers five years later. But in that ballroom on that day, Trump shook the rafters and planted the seeds of his historic White House victory.

It is not difficult to gauge the potency of a political presentation by the intensity of the audience response, but the excitement Trump aroused was exceptional. The CPAC crowd loved Trump’s message—not his theatrics or his celebrity, but his message—and the fervent reaction to him far out-stripped that of every other speaker, including the many White House hopefuls who sought the GOP nomination in 2012. Soon after Trump’s CPAC event, I appeared on television and made those points. I did not in any way endorse Trump’s remarks, of course, but merely conveyed the force and power of his display. I said that if Trump chose to enter the Republican presidential nomination fight, his potential should not be underestimated.

Trump was watching the television segment. One sure thing about Donald Trump back then, which is still true to this day: If you said something favorable about him on television, he would call you on the telephone and tell you how smart you are. He phoned me up, thanked me for my comments on his CPAC speech, and invited me to come by Trump Tower and have a little talk about politics. Trump had been a fixture in business, pop culture, the gossip rags and the modern American psyche since my youth. And for all his cartoonish swank, he was a fascinating figure. Now he was making waves in the world of politics. I accepted.

I arrived at Trump Tower on time, was ushered into his office suite on the twenty-sixth floor, and was told Trump was running behind schedule. Before I settled in to wait, his top in-house political aide scooped me up and led me to his own small office to discuss the viability of a 2012 Trump presidential campaign.

That aide was Michael Cohen, Trump’s personal lawyer and fixer, who later became caught up in Robert Mueller’s wide-ranging investigation into possible collusion between the Russian government and the 2016 Trump campaign. Cohen publicly broke with his long-time boss, confessed to Mueller, and in December 2018, was sentenced to three years in federal prison after pleading guilty to crimes including campaign finance violations and tax evasion, a “veritable smorgasbord of fraudulent conduct,” according to the judge who sentenced him.

At the time of my visit to Trump Tower in 2011, Cohen was the main public face and point of contact for an exploration into a Trump presidential bid, as his boss taped episodes of The Apprentice, marketed his brand, dallied with real-estate deals, and dipped his toes in and out of the political waters of Iowa, New Hampshire and beyond. Cohen gabbled about “Mr. Trump” with a breathless reverence that was almost laughable, as if the mogul were some combination of Solomon, Hercules and Elvis Presley.

I had spoken to Cohen on occasion over the previous few years and was prepared for the song-and-dance boosterism I heard that afternoon: that Mr. Trump was in demand all over the country to give political speeches and share his thoughts on the issues of the day. That Republican Party officials in Iowa and New Hampshire were begging him to run. That the reaction to Mr. Trump’s every appearance and event was electric, revolutionary.

Trump and Cohen are very different men, but at the time they were identical in one respect: the ardor with which they could discuss the brains, talents, and general splendor of Donald J. Trump. One tends to absorb such hyperbole with more than a touch of skepticism. I listened with patience and reserve. Then Cohen brought out the binders.

They were filled with letters. Dozens, scores, hundreds of letters. Cohen told me heaps of letters arrived in the mail every day, sent by strangers from all over the country, and that Trump’s secretarial team collected, sorted and organized them into binders. Some were handwritten; some included checks, or five- or ten-dollar bills, or small mementos. All beseeched Trump to run for president.

Cohen flipped through the pages of plastic-encased correspondence, reading aloud from particularly heartwarming, impassioned or resonant missives. You HAVE to run…America needs you…My children’s future depends on it…The career politicians will never fix our problems. Cohen’s face was alight with devotion, urgency, pride. Idly, I wondered if the letters were genuine. Perhaps they had been generated by a team of underpaid foreign workers; or by the Trump Organization administrative staff; or by Cohen himself, laboring as if over an elementary-school art project, with floral stationery, scratch pads, postcards, inkwells, ballpoint pens and typewriters from eBay set out before him.

But the language in these letters was genuine, the words evocative. Many of the letters echoed the message Trump had delivered at CPAC and other venues. There were citizens all over the country, a significant portion of the electorate, who were struggling, grievously unhappy and afraid. They were in trouble, and they thought America was in trouble, too. They had seen this man on television, this man who had so much confidence and so many glib answers, and they wanted him to go to Washington and set things right.

When politicians are deliberating over joining a presidential race, it is common for them to boast that a diverse array of Americans is encouraging them to run. While there is often truth to this claim, the appeals usually come from staff, close friends and loyal donors who have offered regular support over the years.

Cohen’s binders of letters, the outpouring of promises and pleas, were perhaps unprecedented in modern times. The people who wrote to Trump nearly a decade ago would be disappointed when he announced in May, 2011 that he would not be entering the 2012 presidential race. “This decision does not come easily or without regret,” said Trump in a statement, “especially when my potential candidacy continues to be validated by ranking at the top of the Republican contenders in polls across the country. I maintain the strong conviction that if I were to run, I would be able to win the primary and ultimately, the general election.”

Four years later, those binders of letters, I believe, helped inspire Trump to make his victorious bid for the White House. They served as more than an ego stroke, more than the typical fan blandishments dashed off to a reality TV star. They were a tangible sign that the people were waiting for him. Despite the media mockery, despite the dubious mutterings and nervous sneers from the Republican Party, the letters in those binders were the start of something bigger than a campaign. They were the start of a movement.


Excerpted from How to Beat Trump: America’s Top Political Minds on What It Will Take, by Mark Halperin. Copyright 2019 by Mark Halperin. Reprinted with permission from Regan Arts. All rights reserved.



  1. Interesting article but it fails to mention why these people were writing those letters and the opening Trump saw. The Republicans had vacillated between ignoring the Tea Party and playing lips service to it. The Republicans thought where else would the Tea Party go? For this reason Trump’s coattails are relatively short. The congressmen congresswomen and Senators who should be benefiting from a Republican presidency are seen more as the establishment and not with the maverick Trump. What no one in American wanted to see in 2016 was Bush v. Clinton. The Republicans made this known in the primaries. The democrats decided to stand pat. The rest is history.

  2. Substitute “despite” with “because of” and the sentence above will yield more information. “Because of the media mockery, because of the dubious mutterings and nervous sneers …”

    Yeah sure, Trump is bombastic, Trump is … fill in the blank, these are things I usually agree with but why is it so important to continually virtue signal Trump’s short-comings when it was never important to similarly do so with his opponent’s corruption or be embarrassed by his predecessor’s inability to give even a short speech without a teleprompter and saying I, me, mine every minute.

    In 2012 despite being a lifelong newshound, I simply dropped out. It seemed pointless to be informed when the presidential choice was, again, two clueless members of the same governing party whose main goal in life was to be liked by the editorial board of the NY Times. It was only when Trump won in 2016 that it appeared something must have changed. Looking back to see that Trump was mocked during the campaign for being critical of policy towards China, when that appeared the only sensible conclusion, it was clear the critics in the ruling class were no longer up to their job. To many it was also becoming conspicuous that elites at universities, the media and government no longer gained their positions because they are the best and brightest but because they are the ones willing to conform, join the club, and adopt the same values and groupspeak. These conformists upon entering their intellectual ghetto mistook their groupthink for wisdom and their consensus for scientific proof.

    Living in a college town I am continually amazed at the mediocrity that dominates the “education” process, not to mention the massive debt burden foisted onto those who are subjected to it. While students are burdened by debt the uninspired elites are inordinately rewarded despite the their puny results regardless the institution they inhabit. This mediocrity appears to have permeated throughout the culture to such an extent that many of my peers also in their sixties have expressed they see the same change, they now expect less understanding and more stupidity from those running institutions. We see more wisdom from the person who works on our car or fixes our plumbing and certainly a lot more humility which should be the fount of wisdom.

    The lords and prelates from the middle ages have crept back into power, revoked the enlightenment and are bent on imposing a new religion. Apparent in my four year hiatus after 2012 there was a wave of recognition building, Trump didn’t create it but he was able to see it and despite his shortcomings or maybe because of them, he was able to ride it. So for those who assert the deplorables who supported him were stupid or racist or bigoted, please look in the mirror to see a real bigot.

  3. What the article clarifies is that Trump is, first and foremost, and entertainer. He reads the crowd and tells them what they want to hear. Unlike most stars he acts as his own booking agent, and has done a good job of figuring which “next gig” is best for his career. On that score he has been brilliant. His run for the Presidency simply took advantage of the way the press has spend decades trivializing the election process, turning one of the most serious decision in our democracy into entertaining, content-free horse race.

    And now we President Trump, a brilliant entertainer who is unable to tell the difference between the stage set and the real world.

  4. And what a glorious run it’s been. I’ve enjoyed the endless, unceasingly monotonous menarching from my betters in the academy, media, entertainment and news media.

    You know the “resistance” snicker.

    And yet they still mock, demonize and fail to understand what happened. Quit fellating yourselves, pull the finger out of your ass and put it up to the wind and…listen.

    Oh never mind, people of such high intellect and class (how do I know this? They tell us so …every.chance.they.can) wouldn’t piss on the likes of us if we were on fire.

    Keep doing what’re you’re doing genius, it worked masterfully the last time.

  5. Real Stable Genius

  6. As opposed to his predecessor, who couldn’t distinguish the campaign trail from the real world. Or was it the classroom from the real world?

    Either way, a far cry from the modern representative Democrat, who can’t distinguish the real world from a Margaret Atwood novel.

  7. A Quillette article that doesn’t assume a disdain for Trump? Surprising! I thought the speculation that the letters were fake paranoid and uncharitable, but seeing what book this is from, it is to be expected.

  8. The author makes too much of these letters when he describes them as “the simple secret of Trump’s supreme political confidence.”

    Most people who voted for Trump did so for two simple reasons: 1) they detested the other Republican candidates, and 2) they detested Hillary Clinton.

  9. “they detested Hillary Clinton”

    I can only speak for myself, but I think mostly this.

  10. Good article.

    I think many have forgotten H. Ross Perot, who raised many of the same issues - trade, Mexico, foreign affairs and militarism, saving domestic manufacturing jobs, patriotism/nationalism - in 1992 that Trump won on in 2016. Two key differences were Perot focussed on balancing the budget, a worthy goal but not one that creates excitement, and he favoured increasing income and fuel taxes. Nevertheless, his appeal was powerful and undeniable. Perot was leading the polls until he self destructed in the summer of '92 by ceasing his campaign during those crucial campaign months. Still, he took nearly 1/5th of the vote as a third-party candidate, which is a very solid base to build a campaign if you know how to tap it. Perot was a technophile, though he pre-dated the wide roll out of the internet and social media. Trump used many of the same populist and economic nationalism messages plus he had social media’s tools to bypass the media gatekeepers. Perot had to rely on Larry King Live and infomercials.

    “In plain Texas talk,” Perot said, “it’s time to take out the trash and clean out the barn.” Trump shortened that to “Drain the swamp.”

  11. @gagamba

    IMO, had the electorate been as disenchanted with the Republican Party as they became in 2016, Perot might have taken the Republican nomination. He was before his time.

  12. The article was OK, he wrote what he saw and does seem to ‘get it’ to a short extent, unalike 99% of his media pals…

    I however was really drawn to the authors bio section, there in listed a book he just wrote;

    "How to Beat Trump: America’s Top Political Minds on What It Will Take*

    LOL, good luck with that,because a) there were 16 other GOP candidates who couldn’t figure it out when the nomination process started, and b) the ‘finest’ political brains in Hillarys camp, the entire and I mean entire media apparatus, pollsters etc. couldn’t figure it out either…which makes Halperin imho, something of a con man…like the ‘consultant class’ or Cohen;)

  13. Indeed, this article is thinly veiled Trump hate. We hardly need more of those in this world; not sure why Quillette bothered to host it.

  14. I remember in 2013 when Bitcoin was just emerging in the mainstream. At the time, financial pundits had no idea what it was, and had nothing similar to compare it too. As a result, they were forced to base their analysis on what they knew about economics and finance. The results were both disastrous and revealing.

    There are plenty of articles from 2013 criticizing the bitcoin bubble with spurious claims about how economics and finance worked (It was about $140 at the time it went mainstream, as of me writing this post its north of $9000.00). Bitcoin, of course, has plenty of problems, both technical and economic, but the pundits were just so wrong in articulating the problems with Bitcoin which left me wondering if they knew anything at all.

    The best statement regarding money circa 2013 was probably this gem, by Felix Salmon, a financial and left wing political pundit:

    Because it turns out that financial-services companies are a very important part of any democracy.

    It’s because we place so much trust in banks, after all, that they are forced to take on a great deal of responsibility. Banks and central banks are given an important job to do, are regulated and scrutinized, and can be held responsible for their actions. The population of the entire country, as represented by the government, stands behind bank deposits and promises to honor them even if the bank goes bust. Money, in other words, is a key ingredient in the glue which keeps the social compact together.

    There it is, bitcoin is bad because it undermines the financial services industry which, apparently, represents democracy.

    I’m mentioning all of this because it reminds me of current events. That is, in a lot of ways, Trump is the Bitcoin of politics. He’s audacious and flawed in many respects, but brilliant in some respects as well.

    Because he is so unconventional and hated so much, his political detractors struggle to articulate why he is wrong but feel compelled to say something, anything, to take him down. In many cases, they reveal their own ignorance in the process.

    Its not the media that is exposing Trump, its Trump that is exposing the media. And that’s why I like watching him.

  15. Fixing the country’s trade imbalance also undermines the financial services industry, I was surprised how much they make financing the trade imbalance. How many other areas are there where the national interest and the banking industry diverge? While it is in our interest to have a sound financial system I would keep them far away from trade and policy decisions and when their expertise is required it should be done in a well lit room with good recording equipment in operation.

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