Stepien, a 40-year-old New Jersey operative, is an Establishment Republican out of central casting: trim, well dressed, and with impeccable hair. He was recruited to join the Trump campaign in August 2016, after befriending Kushner, and his current job is to effectively reverse-engineer a method to Trump’s madness. Despite the gloomy outlook for Republicans—a recent Real Clear Politics poll average showed Democrats with a six-point advantage—Stepien did his best to spin the White House’s message that Republicans could limit the damage in the midterms. “This is not an easy time to run and win as a Republican,” Stepien conceded. “[Trump] is trying to get all the people who voted for him in 2016 back out to the polls in 2018. The goal is to make those people who are presidential-year voters into midterm-election voters.”
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).
Colbert chimed in to explain why he didn't want Trump to pull himself out of the race, saying: "I think it's important that the voters of America have an opportunity to say 'Oops, my bad. We've made a mistake there.' ...If Donald Trump doesn't run he takes away that corrective action of history and therefore his presidency is whole and unjudged if he just doesn't run again."
Not everyone is on board with this program. With eyes on 2020, Ivanka Trump and Jared Kushner are pushing Trump to adopt more moderate positions. Kushner aggressively lobbied his father-in-law to embrace prison reform, organizing a White House visit with Kim Kardashian West and consulting with CNN host Van Jones. Jones told me Trump liked the positive media coverage that followed his commuting the sentence in early June of low-level drug offender Alice Marie Johnson at the urging of Kardashian and Kushner. “Trump was pleasantly surprised,” Jones said. According to a former White House official, Kushner and Ivanka have also been polling more inclusive language on transgender rights. “The 2020 campaign is about the rehabilitation of Jared and Ivanka,” the source said. In late June, one outside Trump adviser explained to Kushner that the population of white voters shrinks by one million every year. Kushner expressed alarm at the speed of the changing demographics, a source familiar with his thinking told me. (A Trump official denied that Jared and Ivanka are playing any role in polling, campaign activities, or decision making.)
Trump, who filed the paperwork for “Make America Great Again” just days after Mitt Romney lost the 2012 election, announced his already-arrived-upon 2020 slogan in a just-published interview with The Washington Post's Karen Tumulty. The reveal comes in the middle of a must-read interview in which Trump seems to decide, on the spot, to nail down the new slogan and share it with the world.
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In December 2016, Time named Trump as its "Person of the Year". In an interview on The Today Show, he said he was honored by the award, but he took issue with the magazine for referring to him as the "President of the Divided States of America." In the same month, he was named Financial Times Person of the Year. In December 2016, Forbes ranked Trump the second most powerful person in the world, after Vladimir Putin and before Angela Merkel. In 2015, Robert Gordon University revoked the honorary Doctor of Business Administration (DBA) it had granted Trump in 2010, stating that "Mr. Trump has made a number of statements that are wholly incompatible with the ethos and values of the university."
Although Trump's early campaign filing is extraordinarily unusual, aspects of a "permanent campaign" are not entirely unprecedented in American politics. Such a phenomenon had a presence in the White House at least as early as the presidency of Bill Clinton. Under the advice of Sidney Blumenthal, Clinton's staff continued to engage in campaign methodology once in office, using polling for assistance in making decisions.