CHAPTER 5

Preparing to Seek the Grand Prize

Trump had supported George W. Bush for president in 2000, though he wasn’t especially active in the campaign. Like most Americans, he enthusiastically backed the president’s energetic policy against terrorism after the September 11, 2001, attacks on the World Trade Center and the Pentagon. He claims to have disapproved of the Iraq War of 2003, though earlier he had said to Howard Stern that he “guessed” he would approve such a war, which was unleashed six months later. That is a reconcilable position and he was prescient in describing the war as botched just a few days after it began.1

In any case, when defense secretary Donald Rumsfeld and the appointed Iraq administrator Paul Bremer dissolved the armed forces and police of Iraq and told the four hundred thousand people involved that they were unemployed and without benefit but could keep their weapons and munitions, it is hard not to wonder what they were thinking. Trump was already a war critic by the time this ordinance took hold, and he remained so; a strong advocate of fighting terrorists, defending the international interests of the United States, but not of plunging unthinkingly into foreign wars, and not of taking on the task of building democratic states where there was no precedent or fertile ground for one. Having opposed the Iraq War more or less in the first place, Trump was appalled, as were most Americans, at the fiscal, strategic, and humanitarian disasters that Bush and Obama had managed to fashion from it.

By 2008, Trump’s own extensive polling confirmed and amplified other polls, which showed that the country—suffering from war fatigue, big government Republicanism, and a looming economic crisis—was disgusted with the performance of all branches of their government, except the military. The whole political battle in 2008 was for the Democratic Party nomination between Hillary Clinton and Barack Obama, as the banking crisis and the ensuing Great Recession, as well as the interminable open sore of the Iraq War, assured the defeat of the Republican nominee, Senator John McCain, who though a distinguished man, was an inept blunderbuss as a presidential candidate. Obama’s masterly victory over Hillary Clinton offered Americans the opportunity to put the racism of their national past behind them by electing him their president, which they happily did, twice, given the Republican alternatives on offer—first McCain and then the equally inept Mitt Romney.

Some space must be allowed for the maturation of Trump’s political judgment during this period. He has been taxed, for instance, for having sent Democrat Eliot Spitzer a hand-written letter of congratulations when he was elected attorney general of New York in 1998 and for having supported Spitzer when he successfully ran for governor of New York in 2006. Spitzer was a very belligerent and draconian prosecutor, who didn’t hesitate to intimidate boards of directors of a target with threats of spurious indictments, and as governor was forced to resign in 2008 after a prostitution scandal, taking with him the sympathy of no one. Trump described Spitzer in 2013 as a “horrible governor and attorney general.” This has been cited as evidence of Trump’s inconstancy,2 but that is not a reasonable conclusion. It came fifteen years after Trump’s congratulations to Spitzer on being elected state attorney general, and is not an unjustified opinion of Spitzer’s performance in office.

Moreover, while Trump’s political views remained largely constant, his party affiliation did not, as he tried to find and support a party that reflected his own beliefs. Trump changed political parties no less than seven times between 1999 and 2012. Trump initially saluted Barack Obama’s qualities as a gifted politician, when he was elected a United States senator from Illinois. But Trump became a sharp critic of Obama as president, and was one of the leaders in the early 2012 polls to take the Republican Party nomination and challenge Obama, then running for reelection. Not content with attacks on Obamacare and other elements of Obama’s rather thin record of accomplishment, Trump embarked on the hare-brained allegation that Obama was not eligible to hold the office of president because he was not born an American. Obama finally produced his long form birth certificate and the whole issue collapsed.

Obama drew extensive laughter when he asked, in Trump’s presence at the annual Washington Correspondents’ Dinner in 2012, if Trump would now move on to the question of: “Did we fake the moon landing?” The comments rankled, but Trump declined to run for president in 2012, and instead campaigned for Mitt Romney, and went to what he hoped would be Romney’s victory party in Boston on election night. He was apparently quite upset by the result, and fired off a torrent of comments in his newly favored medium, Twitter, calling the election, in words that he would make familiar in another few years, “a total sham and a travesty.” He called upon Republicans to “fight like hell and stop this great and disgusting injustice.…We can’t let this happen. The world is laughing at us.”3

This is somewhat Trump’s technique: if he didn’t win, it was fixed—and then he will claim to have won anyway. In this case, he could claim victory by pointing to Republicans maintaining their majority in the House of Representatives, but he also had a more personal plan. Less than two weeks after the election, Trump filed a patent and trademark application on Reagan’s slogan of twenty years before: “Make America Great Again.” In 2012, Trump turned sixty-six. If he was going to make a serious attempt to crown his career with the uniquely great office of president of the United States, it was 2016 or never.

Issues on which he had experience and expertise—real estate (via the housing bubble), banking, the economy—had risen to prominence. During the 1990s, Trump had watched in rising dismay as President Bill Clinton had inflated the housing bubble, by executive order and legislation, enjoying the political benefit of increased home ownership at no apparent cost to the taxpayers, as well as the tangible gratitude of the building trades unions and real estate developers. As Trump was one of the country’s greatest authorities on most aspects of real estate development, he was increasingly concerned with the problem, especially after his own recent debt crisis.

And after the economy almost collapsed in 2008, he consoled himself with the spectacle of the bankers who had put him on the rack (crying like starving children for government assistance to avoid the complete failure of the banking system). It would have been a challenge to make Donald Trump a greater cynic than he already was about the claims of probity and impeccable motive of the captains of industry and capital, but the shambles of international finance in 2008 and following years managed it. The politicians from right to left who had enabled and fostered the crisis, led by Presidents Bill Clinton and George W. Bush and Senator John McCain, locked arms and blamed the crisis on private sector greed, and then acquiesced in the legislative demand for greater powers to assist the federal government in preventing what had occurred, despite the fact that Congress, the president, and the federal bureaucracy already possessed all the powers they needed to avoid it, and, in fact, were the chief architects of the problem.

In 2009, President Obama had entered office with a strong mandate and the good will of everyone, including Donald Trump, as the absurd and unjust color barrier to the nation’s highest office was shattered. Indicative of the wave of hope that accompanied him into office and for a time after was the award, on October 9, 2009, not nine months into his presidency, of the Nobel Prize for Peace. The reason given was his “Extraordinary efforts to strengthen international diplomacy and relations between peoples.” This was nonsense, and the secretary of the Norwegian Nobel Association, Geir Lundestad, stated six years later that the award was an attempt to “strengthen” Obama’s position and not a reward for anything he had done, and that it was a mistake. George W. Bush’s trigger-happy war-making and nation-building, capped out by the economic debacle of the housing debt crisis and Great Recession, so demoralized America and the world that the articulate, suave Obama, representing multiethnic tolerance and racial justice, was accepted at face value by almost everyone. This made the disappointment of his ineffectual performance in office more bitter.

He enjoyed a respectable personal approval rating, probably because the country did not want to digest the thought that the first non-white president was not a good president. But in fact, he was not. Polls revealed that the American people thought their country was on the wrong track, and on a wide range of policy issues opposed President Obama. Objectively, the twenty years from 1996 to 2016 gave the country the worst economic crisis since the Great Depression, and with the exception of the Great Depression, the worst since the 1870s; as well the worst peacetime public sector debt accumulation in American history with only 1 percent per capita GDP growth to show for it.

More than a trillion dollars had been squandered in Iraq, to hand three-fifths of it over to Iranian influence and reduce the rest to violent civil and sectarian war. An oceanic flood of desperate refugees was loosed upon the Middle East, North Africa, and Europe, as the United States itself continued to admit unassimilated masses of illiterate Latin American peasants as undocumented migrants. Gross Domestic Product per capita growth declined from 4.5 percent in the last six Reagan years to 3.9 percent in the Clinton years, to 2 percent under George W. Bush and 1 percent under Obama. In Obama’s eight years, food stamp use and the percentage in defined conditions of poverty sharply increased. The work force shrank by more than ten million people, though the population grew; and twenty-three million single Americans between the ages of thirty-five and fifty-four, the prime of a person’s working life, were completely idle. A great many of them were sustained on immobilizing anti-depressants supplied by expanded Medicaid access.

All three recent presidents had blundered in foreign policy. In the case of North Korea, that mismanagement had led to the point where the incoming administration in 2017 would be facing an imminent nuclear threat from Pyongyang. With regard to Iran, a distinct minority of Americans approved of Obama’s attempt to placate the Iranian theocracy, the principal terrorism-sponsoring state in the world, with a slightly and conditionally delayed green light to deploy its own nuclear weapons.

Donald Trump got around the country a great deal and had an enormous number of contacts in almost every section of the population. He could see opinion building like a pressure cooker, especially among blue-collar conservatives alienated not just from the direction President Obama was taking the country, but from the establishment Republican Party that was supposed to offer a political alternative. Trump himself did not take naturally to mastering policy issues, but he had a good idea of what a very large number of people were against, and he knew from his preliminary run in 1987 and again in 2000 that a third party could not win. There would be no incumbent president running in 2016, and the country was angry at both parties. Both George W. Bush and Barack Obama, by normal measurements, had been unsuccessful presidents, and the first unsuccessful presidents to be reelected. Presidents who had been unsuccessful in the past, either did not seek reelection (Pierce, Buchanan), or sought reelection unsuccessfully (Van Buren, Benjamin Harrison, Hoover, Carter). Some presidents were adequately successful but were politically out-maneuvered (John Adams and John Quincy Adams, Cleveland, Taft, George H. W. Bush); and Polk and Hayes were successful presidents but declined to seek reelection. Trump, then, approached 2016 in an almost unique position, where there would not only be no incumbent, but where the American people, reelecting for a lack of other choices, two unsuccessful presidents, were now looking for a dramatic change. That, he realized, offered an opening for a non-establishment candidate.

Trump, however, did not spend the Obama years entirely torqueing up for a possible presidential run. The coils of the casino industry were not so easily snipped. An inordinately lengthy time was required for Trump to get free from the imbroglio of Atlantic City. He was dogged by press skepticism about the proportions of his net worth, though there was no longer any question about his solvency. The casino boom in Atlantic City from which he had profited had followed the traditional path to a bust. Too many casinos were built, neighboring states sought the same revenues and licensed their own gambling, and Atlantic City was a decrepit and somewhat out-of-the-way place. The contraction of the Atlantic City boom was painful and difficult, and Trump’s casino company had gone into bankruptcy again in 2004, and the same fate appeared to be stalking it in 2009. Trump was getting too old, and generally prosperous, for this now, and rather than take it through the wringer of bankruptcy again, he simply retired from the company, saying that his economic interest in it was no longer material. It was an agile effort to side-step the issue, but Carl Icahn, Trump’s old and astute ally in many battles, opposed him this time. Trump was supporting a proposal, sponsored by a hedge fund, that the company go through bankruptcy yet again, but give Trump 10 percent of the emergent company in exchange for use of his name. Icahn led a competing offer that would remove Trump completely, adding publicly the acerbic reflection, that if Trump’s name was so valuable, “how come they (the casinos), went bankrupt three times.” Trump didn’t answer, but Icahn’s bid was unsuccessful.

Relations with Icahn were patched up (and the strength of the Trump name has been demonstrated), but the casinos again went into the tank in 2011. The Trump Castle Casino was finally sold for about 8 percent of what Trump paid for it, though he had taken a lot of profit from it over the years, and he parked most of the capital loss on bond-holders. As always when in retreat, he congratulated himself—in this case, for departing the Atlantic City Casino business at the right time. The Trump Plaza and Taj Mahal casinos went back to the bankruptcy trough in 2014, as four of Atlantic City’s twelve casinos closed, in a Darwinian effort to restore commercial viability to a down-sized industry. Icahn returned to the fray and gained control of these assets in 2016. By this time, he was a public supporter of Trump as a political candidate, but was guarded in his commendation of him as a businessman. It was messy, but Trump had at least got clear of it all well before there was any need to start organizing politically for 2016.

The subject of Trump’s wealth, not that it much matters to anyone except himself, as he is obviously a very wealthy man by the standards of all but a handful of people in the world, is difficult to assess precisely. He owns the commercial space and three-story penthouse in the Trump Tower, the Trump Building at 40 Wall Street, a number of valuable properties on East 41st, East 57th, and East 61st Streets, all prime locations. He has a sizeable interest in and the management of 1290 Avenue of the Americas, a forty-three-floor, top-end office building, and a substantial number of very high-quality golf courses and many lucrative real estate branding and licensing agreements. He owns Mar-a-Lago, a money-spinning private club in a unique location, built from one of the greatest and most famous mansions in America. He owns parts of many other projects, none of which seem now to be controversial. It could probably be assumed that Trump has substantial other assets that are not visible, and that his income streams benefit from the most agile tax planning that can be had. The Federal Election Commission in July 2015 released filings from Trump indicating a cost value of his assets of $1.4 billion, against liabilities of $265 million, but his campaign, presumably thinking it a vote-winner, said that the real asset values were about $10 billion (likely the customary truthful hyperbole but probably not more than two or three times the real figure). He made, and did not inherit, billions of dollars, and became a television star and remained one for many years, and in his first try at politics, was elected president of the United States; whatever happens after this, he has already had a career of astonishing achievement, though he is still unlikely ever to lead a cotillion.

Another subject that his always noisy critics focused on was his charitable endeavors. Trump frequently cites his charitable donations, and his enemies just as frequently try to debunk them. In May 2016, a long-standing critic in the New York Post, David Fahrenthold, exposed that Trump had promised to donate a million dollars of his own to veterans’ causes, but had not done so. There had been many stories trying to pick holes in Trump’s filed claim of having donated $102 million to bona fide charities between 2011 and 2015. This was shown to include the donation of free rounds of golf at his many fine golf courses, and other such prizes auctioned at charity benefits. There was particular emphasis on the donation of a free, chauffeured ride given to tennis star Serena Williams to attend a tennis tournament, and the donation of a framed, autographed portrait of himself. The value of the autographed portrait was $1,136.56. Trump was understandably irritated that such an item (submitted by his accounting staff), should be hyped in the obsessively negative press, and angry that it overshadowed his donation of more than one hundred million dollars to certified benevolent causes.

In response to Fahrenthold’s sniping, Trump called a press conference at the Trump Tower, and announced that he had successfully canvassed donations of $4.6 million dollars for veterans’ causes, and that he had, as he had promised, made a personal cash donation of one million dollars to the Marine Corps-Law Enforcement Foundation, bringing the total contribution to $5.6 million dollars—short of his target of $6 million, but still a tidy sum. He handed over this total, and noted that interest on the gift would quickly bring it to the campaign goal. For a man claiming such wealth, coming up with nearly $6 million did not require a back-breaking charitable campaign, but he had done what he had promised and should not have been subjected to the carping insolence of penurious journalists, who are poorly qualified to judge the generosity of others. At his press conference, Trump attacked the media treatment of his charitable activities as “dishonest” (frequently it was), and he singled out one television reporter as “a sleaze” (on normal probabilities, quite likely an accurate description). Trump was serving notice not only that he would not hesitate to attack the press as events unrolled, but that he knew how profoundly the public distrusted the media, and, in his opinion, with good reason.

As on several previous quadrennial occasions, speculation of a possible Trump campaign for the presidency was bruited about in the media, though it was understood that this time, it would be a contest for the Republican nomination, which was thought to be wide open, with no clear leading candidate for the first time since Barry Goldwater and Nelson Rockefeller contended for the honor of being buried by President Lyndon Johnson in 1964. Trump had spruced up and been more selective in his pursuit of public approval in the preceding decade. Not only were there no more ludicrously entertaining wrestling appearances, but he phased out unpromising applications of his brand, and did fewer profitable but lightweight inspirational addresses; further, he consigned to the complicated and incomprehensible attrition of litigation any and all disgruntlement over Trump University. But the polyglot army of his critics and skeptics were confidently lying in wait for him, and the more febrile opponents publicly beseeched him to test his real popularity in the field where they were both self-styled experts and presumptive kingmakers and -breakers. He must make the race, comedian Stephen Colbert and others shrieked, so he could make a complete and irredeemable ass of himself, and satisfy America and the world that the country had not been battered by improvident events into seriously considering such a buffoon for its highest office. As an unfriendly duo of biographers put it: “Late-night comics only hoped he would stay around long enough for them to milk his candidacy for a few laughs.”4

Almost nobody took such an initiative seriously. Trump had considered running for governor of New York in 2014, and he did not, at first, renew his contract with NBC for his ever-popular program, The Apprentice. Many skeptics snarkily assumed that Trump dropped hints of political ambitions merely to keep his name in the news, increase his brand visibility, and boost his ratings. The polite and civilized media, whose politeness rarely extended to Trump, accepted that Trump might be popular with up to 20 percent of the public, but it was not imaginable to any audible commentators except former House speaker Newt Gingrich (who had himself given Mitt Romney a respectable run for the Republican nomination in 2012) that Trump could possibly win a series of primaries in the glare of publicity and with all the baggage he carried from past bankruptcies, indiscretions, and assorted affronts to the conventional wisdom, not to mention generally accepted versions of good taste. If the nation’s greatest blowhard and most vulgar capitalist, leader of the flat-earth level “birther” movement complaining that Obama was ineligible to be president, a known appreciative reader of the National Enquirer, was even considering such a move, it could only be for an ultimate publicity blow-out, the satiation of his own lust for publicity no matter how negative, and a stratospheric escalation of his tawdry and unlimited brand-building mania.

But Trump was in all respects a unique candidate, and had a unique political positioning—the appeal of which his critics didn’t understand. Only one person, Donald Trump, came forward to challenge the whole political establishment—to call the Bushes incompetent, the Clintons dishonest, Obama a failure, the press toadies, the pollsters flacks and lackeys, much of the financial community greedy hypocrites, and Congress a bipartisan group of self-serving and inept insiders who were just gaming the system for their own incumbencies and the devil take the country and its voters. Came the day and the man, on June 16, 2015, the all-time red-letter day in the history of the Trump Tower. Trump’s campaign manager, Corey Lewandowski—a Republican campaign organizer in New Hampshire, whom Trump had hired on the basis of a thirty-minute interview—had written a campaign announcement of under ten minutes. Trump descended the escalator of the grand foyer of the Trump Tower, with Melania and his children, and spoke for forty minutes. The atrium was packed, though some may have been attracted by offers of free Trump tee-shirts and hats. He was fluent, emphatic, and entertaining, and gave a foretaste of what was to come.

He emphasized the issues of illegal immigration; the loss of manufacturing jobs, sacrificed to disadvantageous trade deals and an unquestioned belief in the virtues of freer trade; the sky-rocketing national debt; and Islamic terrorism. He accused the Obama administration, including former secretary of state Hillary Clinton, of not recognizing Islamic terrorism for what it was, and of failing to defend the country adequately against it. Trump promised to finance his own campaign and severely criticized what he regarded as the corruption of the entire political system, from the buying of candidates through dishonest campaign financing, to the buying of votes in Congress by lobbyists. On illegal immigration—in a country with an estimated eleven to twelve million illegal residents—Trump applied the dentist’s drill directly to the politically correct nerves of the Left by saying that illegal immigrants from Mexico were not Mexico’s “best people” and included inordinate numbers of drug dealers, drug addicts, rapists, and other criminal elements, though he conceded that mixed among them were, “I assume, some good people.” He promised “a great, great wall” to end the absurd porousness of seven hundred miles of open country, without even a fence between the United States and Mexico, like the much longer, but uncontroversial border with Canada. The United States, he said, had become “the dumping ground for the world’s problems.”

He promised to promote economic growth, to repatriate jobs with an incentive tax structure that would stop mollycoddling Wall Street deal-makers, to reopen and renegotiate unsuccessful trade agreements, to end the freeloading of America’s so-called allies and the insolence of its enemies, and to redefine the national interest in a coherent line between George W. Bush’s hair-trigger adventurism and Barack Obama’s pacifistic, Panglossian quest to have America’s allies and enemies change roles and places.

The initial reactions, entirely predictable, were mainly expressions of horror, leavened by jubilation from much of the media that the dingbat billionaire had jumped with both feet on a land-mine in his first appearance. It was almost too rich a payout on their hopes for a spectacular fiasco than they had dared to imagine possible. The “blowback,” as Trump called it, was tempestuous: NBC ostentatiously canceled its arrangements with Trump (meaningless given that he had pulled out of The Apprentice, but indicative of the network, and most other networks’ invertebrate response to controversy); NBC also declined to carry Trump’s beauty pageants (but he was selling out of them anyway at a handsome profit); and Macy’s cancelled its sale of Trump’s clothing line, as his campaign announcement was “inconsistent with Macy’s values” (a moral canon whose existence had not previously been suspected). Spanish-language networks Univision and Ora (partly owned by Mexican billionaire Carlos Slim, a large investor in the financially challenged New York Times), and NASCAR, severed their (tenuous) connections with Trump, as did even the Serta Mattress Company (not a heavy blow to the Trump Organization), all to the cacophonous jubilation of most of the media. Hillary Clinton piled on, saying, in the wake of the Charleston shooting, which happened the next day, when a twenty-one-year-old white man shot and killed nine people in an African American church, that Trump had “said some very inflammatory things about Mexicans. Everybody should stand up and say that that is not acceptable.”

This was the beginning of the mighty Democratic smear steamroller that claimed Trump supported and incited racist violence. It was an unjust but not entirely surprising charge; his comments on Mexicans were provocative but not inflammatory. Hillary Clinton’s statement, however, was the first in a long line of assertions that tended to confirm a suspicion that there was no argument to reelect the Democrats on their merits, nor any amber waves of enthusiasm for Hillary to harvest, only the potentialities of discrediting the Republicans. At this stage it was enough to attack a dark horse candidate for that party’s nomination.

A bifurcation had already begun, between the conventional liberal wisdom, encompassing all the Democrats and at least half of the Republicans, 80 percent of the national media and 95 percent of the entertainment industry, and probably three quarters of the limousine liberal community in and in close touch with Wall Street on one side; and a section of popular opinion that was not well represented in the leadership groups of the country but was, from the first days of the Trump campaign, evidently a good deal larger and more capable of flexing its muscles at the polls than complacently received and robotically repeated civic-worthy opinion had remotely thought possible. The day before, former Florida governor Jeb Bush, son and brother of presidents, had announced his candidacy, and revealed that he had a war-chest of $100 million in a PAC (Political Action Committee), called Right to Rise USA.

Jeb Bush was assumed to be the favorite from the start, and Trump’s assurance that he would have no PAC and would accept no contributions, was assumed to be irrelevant as his campaign was not expected to last for more than a few weeks; an amusing sorbet, a circus of the bumptious, before the country got down to choosing between the latest offerings of the Bush and Clinton families that the American political class, with singular lack of originality, would be offering for its delectation, this political season. Almost undetected, the political earth was starting to tremble and a seismic shock had begun to ripple across the country.