While Trump is sui generis, history offers guidance on the folly of predicting distant elections. At this moment in 1989, George H.W. Bush, having kept his promise not to raise taxes and with communism collapsing, seemed invincible. Three years later, he was defeated. In 2009, Barack Obama was in trouble, with unemployment soaring to 10 percent, up sharply from what it was two years earlier, and with his major health-care initiative seemingly stalled in the Senate. Three years later he was re-elected.
Trump acquired his third casino in Atlantic City, the Taj Mahal, in 1988 while it was under construction, through a complex transaction with Merv Griffin and Resorts International. It was completed at a cost of $1.1 billion and opened in April 1990. The project was financed with $675 million in junk bonds and was a major gamble by Trump. The project underwent debt restructuring the following year, leaving Trump with 50 percent ownership. Facing "enormous debt", he sold his airline, Trump Shuttle, and his 282-foot (86 m) megayacht, the Trump Princess, which had been indefinitely docked in Atlantic City while leased to his casinos for use by wealthy gamblers.
Once upon a time, in a distant America, the words “greatest,” “exceptional,” and “indispensable” weren’t even part of the political vocabulary. American presidents didn’t bother to claim any of them for this country, largely because American wealth and global preeminence were so indisputable. We’re talking about the 1950s and early 1960s, the post-World War II and pre-Vietnam “golden” years of American power. Despite a certain hysteria about the supposed dangers of domestic communists, few Americans then doubted the singularly unchallengeable power and greatness of the country. It was such a given, in fact, that it was simply too self-evident for presidents to cite, hail, or praise.
Trump allies — projecting buoyancy about a race the president approaches with historically weak approval ratings — say the bombast reflects his confidence: Trump privately claims to be unimpressed with the Democratic crop, calling its major figures grossly unprepared for prime time and too liberal for the general electorate. Aides and allies said they expect the smattering of public broadsides to pick up significantly after the midterms.
A few days after my visit to the White House, I went to see Bannon, who was holed up in his suite at the Regency in New York, the same hotel where Michael Cohen was ensconced just a few floors away. Bannon was giddy. He was fresh from Rome, where populist political parties he’d supported had just formed an anti-immigration, anti-European Union government. “Populist nationalism is on the move everywhere in the world,” Bannon boasted. Events seemed to be breaking his way in Washington too. “It’s like my white board’s there and Trump is checking shit off,” Bannon said. He marveled at Trump’s border crackdown and decision to launch a global trade war. “Trump is on the full MAGA agenda,” he said. Bannon admitted that he and Trump still don’t speak, but he gets his ideas to Trump through other channels, mainly Lewandowski and Freedom Caucus chair Mark Meadows.
Trump has often said that he began his career with "a small loan of one million dollars" from his father, and that he had to pay it back with interest. In October 2018, The New York Times published an exposé drawing on more than 100,000 pages of tax returns and financial records from Fred Trump's businesses, and interviews with former advisers and employees. The Times concluded that Donald Trump "was a millionaire by age 8", and that he had received at least $413 million (adjusted for inflation) from his father's business empire over his lifetime. According to the Times, Trump borrowed at least $60 million from his father, and largely failed to reimburse him. The paper also described a number of purportedly fraudulent tax schemes, for example when Fred Trump sold shares in Trump Palace condos to his son well below their purchase price, thus masking what could be considered a hidden donation, and benefiting from a tax write-off. A lawyer for Trump said the "allegations of fraud and tax evasion are 100 percent false, and highly defamatory". A spokesman for the New York State tax department said the agency was "vigorously pursuing all appropriate areas of investigation". New York City officials also indicated they are examining the matter.
The concept of a permanent campaign also describes the focus which recent presidents have given to electoral concerns during their tenures in office, with the distinction between the time they have spent governing and the time they have spent campaigning having become blurred. Political observers consider the rise in presidential fundraising as a symptom of the permanent campaign.