In 1996, Trump acquired the Bank of Manhattan Trust Building, which was a vacant seventy-one story skyscraper on Wall Street. After an extensive renovation, the high-rise was renamed the Trump Building at 40 Wall Street. In 1997, he began construction on Riverside South, which he dubbed Trump Place, a multi-building development along the Hudson River. He and the other investors in the project ultimately sold their interest for $1.8 billion in 2005 in what was then the biggest residential sale in the history of New York City. From 1994 to 2002, Trump owned a 50 percent share of the Empire State Building. He intended to rename it "Trump Empire State Building Tower Apartments" if he had been able to boost his share. In 2001, Trump completed Trump World Tower. In 2002, Trump acquired the former Hotel Delmonico, which was renovated and reopened in 2004 as the Trump Park Avenue; the building consisted of 35 stories of luxury condominiums.
On September 26, Trump also attended a campaign fundraising dinner hosted by the Republican National Committee (RNC) in New York City. The event was reported to have raised nearly $5 million, with major donors spending up to $250,000 to dine with President Trump. Since Trump scheduled for a quick meeting with Nikki Haley and other U.N. officials immediately prior the fundraiser, he was able to file the travel expenses related to that visit to New York as "government business", thus making them the expense of the American taxpayer, and not his campaign. Trump's pattern of mixing travel for fundraising activities with travel for government business has drawn criticism from government watchdog organizations.
Trump's supporters have some legitimate grievances. Wages for low-skilled work are depressed, and no longer can a man with a high school education or less expect to work in a factory his entire life and still support his family and retire with dignity. While much of the country is living longer, working-class white men without college degrees are now dying sooner than they used to. The promise of upward mobility is shrinking.
In 1995, Trump founded Trump Hotels & Casino Resorts (THCR), which assumed ownership of Trump Plaza, Trump Castle, and the Trump Casino in Gary, Indiana. THCR purchased Taj Mahal in 1996 and underwent bankruptcy restructuring in 2004 and 2009, leaving Trump with 10 percent ownership in the Trump Taj Mahal and other Trump casino properties. Trump remained chairman of THCR until 2009.
Trump’s electoral base wouldn’t mind a handful of ideological betrayals since rank-and-file Republicans are really here for the culture war stuff and not for the concrete policy anyway. So Trump would enter the 2020 campaign with his base intact but also with the brand as a freethinking moderate who’s at odds with the right wing of congressional Republicans. Democrats would end up nominating someone with a relatively extreme rejectionist profile, and Trump would be in a good position to improve his approval ratings and get reelected.
Ronald Schneckenberg, a sales manager for Trump University, said in a testimony that he was reprimanded for not trying harder to sell a $35,000 real estate class to a couple who could not afford it. Schneckenberg said that he believed "Trump University was a fraudulent scheme" which "preyed upon the elderly and uneducated to separate them from their money."
Trump has never filed for personal bankruptcy, although in 1990 he came within one missed bank loan payment of doing so, agreeing to a deal that temporarily ceded management control of his company to his banks and put him on a spending allowance. Trump claimed to have initiated this deal with his banks as he saw the downturn in the real estate market, but bankers involved in the matter stated they initiated the negotiations before Trump had realized there was a problem. His hotel and casino businesses have been declared bankrupt six times between 1991 and 2009 in order to re-negotiate debt with banks and owners of stock and bonds. Because the businesses used Chapter 11 bankruptcy, they were allowed to operate while negotiations proceeded. Trump was quoted by Newsweek in 2011 saying, "I do play with the bankruptcy laws – they're very good for me" as a tool for trimming debt. The six bankruptcies were the result of over-leveraged hotel and casino businesses in Atlantic City and New York: Trump Taj Mahal (1991), Trump Plaza Hotel and Casino (1992), Plaza Hotel (1992), Trump Castle Hotel and Casino (1992), Trump Hotels and Casino Resorts (2004), and Trump Entertainment Resorts (2009).
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.
A group of Honduran migrants arrives to the Mexican side of the border after crossing the Suchiate River aboard a raft made out of tractor inner tubes and wooden planks, on the the border with Guatemala, in Ciudad Hidalgo, Mexico, Saturday, Oct. 20, 2018. The entry into Mexico via the bridge that connects the two countries has been closed. The main group of migrants have moved about 30 feet back from the gate that separates them from Mexican police to establish a buffer zone. About 1,000 migrants now remain on the bridge between Guatemala and Mexico. Moises Castillo, AP
Some TV executives say the only way for the Trump show to get canceled is for ratings to fall off — forcing the president to fade into obscurity or an awkward fox trot in a “Dancing With the Stars” spray tan. But TV history shows that the most successful series — “American Idol,” “Lost,” “The West Wing” and, yes, “The Apprentice” — don’t see sharp declines in viewership or talk of cancellation until around Season 6.
A recent poll put Bernie Sanders’s approval rating at 75 percent, which makes him the most popular politician in America. He’s the standard-bearer for the populist left whose “Medicare for All” bill, while still a liberal pipe dream, now seems as much of a litmus test for ambitious national Democrats as abortion rights. He will also be 79 years old on Election Day 2020.
During the campaign and the early months of his presidency, Trump said he hoped that China would help to rein in North Korea's nuclear ambitions and missile tests. However, North Korea accelerated their missile and nuclear tests leading to increased tension. In July, the country tested two long-range missiles identified by Western observers as intercontinental ballistic missiles, potentially capable of reaching Alaska, Hawaii, and the U.S. mainland. In August, Trump dramatically escalated his rhetoric against North Korea, warning that further provocation against the U.S. would be met with "fire and fury like the world has never seen." North Korean leader Kim Jong-un then threatened to direct the country's next missile test toward Guam.
Trump has been the subject of comedians, flash cartoon artists, and online caricature artists. He has been parodied regularly on Saturday Night Live by Phil Hartman, Darrell Hammond, and Alec Baldwin, and in South Park as Mr. Garrison. The Simpsons episode "Bart to the Future", written during his 2000 campaign for the Reform party, anticipated a future Trump presidency. A dedicated parody series called The President Show debuted in April 2017 on Comedy Central, while another one called Our Cartoon President debuted on Showtime in February 2018.
During the campaign, Trump often used the slogan, especially by wearing hats emblazoned with the phrase in white letters, which soon became popular among his supporters. The slogan was so important to the campaign that it spent more on making the hats – sold for $25 each on its website – than on polling, consultants, or television commercials; the candidate claimed that "millions" were sold. Following Trump's election, the website of his presidential transition was established at greatagain.gov. President Trump stated in January 2017 that the slogan of his 2020 reelection campaign would be "Keep America Great" and immediately ordered a lawyer to trademark it. Trump tweeted “MAKE AMERICA GREAT AGAIN!” on September 1, 2018, apparently in response to Meghan McCain telling about 3,000 mourners at John McCain’s memorial service “The America of John McCain has no need to be made great again because America was always great.” 
Even in the so-called golden age of TV, Mr. Trump hasn’t just dominated water-cooler conversation; he’s sucked the water right out, making all other entertainment from N.F.L. games to awards shows pale in comparison. “The Russia probe, Kavanaugh, Avenatti, Rosenstein, Cohen, Flynn, Papadopoulos — we’re a wildly creative community, but this is peak TV,” said Warren Littlefield, who oversaw NBC Entertainment in the era of “Friends” and “The West Wing.” (He says “The Apprentice,” a ratings juggernaut, killed quality scripted TV in 2004, when it got the coveted 9 p.m. slot on Thursdays, a move made by his successor, Jeff Zucker, now president of CNN.)
The reports gave rise to speculation that not only was the president’s re-election campaign itself ordering campaign items produced in China rather than in the U.S., but that they were attempting to mitigate against the increased costs that would come with the tariffs by pushing for the quick completion of those materials — moves that would provide a double dose of irony for a politician who has famously emphasized prioritizing American jobs and manufacturing.
But the biggest liability for Trump is himself, as evidenced by his disastrous Putin press conference. “For Trump’s outside supporters, we are highly concerned the president is continually incapable of discerning between meddling and collusion,” Sam Nunberg said. “Every time he does something like that he makes our lives harder. It’s time he gets the fuck over [the election].” Even if he survives the Mueller probe and holds on to Congress, there’s the Michael Cohen time bomb. “Michael Cohen and the Trump Org? I don’t know,” Bannon said with concern when I brought it up. “That’s not my deal.” It will be difficult to rekindle the magic that propelled Trump to victory last time.
Presidential approval ratings have shown Trump to be the least popular president in the history of modern opinion polling as of the start of his second year in office. Early polls have shown Trump trailing by a margin of 10–18 percent against several hypothetical Democratic candidates, including Bernie Sanders, Joe Biden, Cory Booker, Elizabeth Warren, and Kirsten Gillibrand. In 2018, the presidential reelection effort and the Congressional midterms both drew presidential campaign attention.