The billionaire industrialist insists that he has broad national support and can win a general election. This resolute confidence about winning elections does not come from a history of winning elections. He has never won one.
Trump has also changed his party affiliation at least four times in the last 16 years — an average of once for each presidential election.
In 1999, as he geared up for a previous, failed presidential quest, Trump quit the Republican Party to join New York’s version of the Reform Party. “I am convinced the major parties have lost their way,” he said. “I really believe the Republicans are just too crazy right,” he also explained.
In 2001, Trump then publicly switched his allegiance to the Democratic Party and apparently remained a committed Democrat for six years.
In 2007, he quit the Democrats. “I’m very much independent,” Trump told Wolf Blitzer. “I really am much more attuned to the people, as opposed to the party.”
Two years later, in 2009, the real estate executive decided he’d had his fill with independence. He registered as a Republican, at least in name.
Earlier this month, Trump clarified his desire to run for president as a Republican as long as he is “treated fairly” and wins the GOP nomination. He also said he had been “part of the establishment” until an abrupt departure in June 2015.
“I want to run as a Republican,” he said in an Aug. 11 press conference. “If I win the Republican nomination, I guarantee you all sitting there, I will not run a third-party candidate.”
In addition to perpetual party-switching, the 69-year-old tycoon has established a sustained record of habitually inconsistent political positions that clash dramatically with the current tide of American conservatism.
An in-depth study of Trump’s declared views on issues ranging from immigration to abortion to taxes to socialized health care shows that, in many ways, he would find a cozy home in progressive circles. (RELATED: From Immigration To Abortion, Longtime Democrat Donald Trump Must Reckon With His Rich Progressive History)
In the second of two installments, The Daily Caller focuses here on Trump’s enthusiastic support for single-payer health care, high taxes and an array of Democrats.
Trump’s love for single-payer health care and Obamacare
Trump has been a longtime proponent of single-payer health care funded by federal largesse. He has also heartily endorsed Obama’s signature Patient Protection and Affordable Care Act.
In his 2000 book, “The America We Deserve,” Trump urged Americans “to reexamine the single-payer plan” and hoped “to improve on the prototype” of national health care implemented in Canada and the United Kingdom.
In 1999, Trump said he was growing more liberal on the subject of health care. “I’m quite liberal and getting much more liberal on health care and other things,” he told Larry King at the time. “I really say: What’s the purpose of a country if you’re not going to have defensive and health care?”
In the same interview, Trump called national health care “an entitlement to this country if we’re going to have a great country.”
In this prior incarnations as a politician, Trump urged a health care plan that was remarkably similar to the individual mandate Obama eventually formulated. Specifically, Trump proposed taxpayer-subsidized “health marts” which would establish competing plans for a federally-created, centralized marketplace.
In June 2009, nine months before Obamacare became law, Trump called an early version of the law “noble.” but expressed concern about its costs.
“We are really a debtor nation right now, and I just don’t know how a country in this kind of trouble can afford it,” the four-time bankrupt property tycoon told Greta Van Susteren on Fox News. “I love the idea, but can this country afford it?”
Trump is also no fan of a flat tax. In “The America We Deserve,” he rejected the concept, calling it unfair to the working poor. “Only the wealthy would reap a windfall” from a flat taxation scheme, he said, and a flat tax would not “raise enough revenue to keep the government operating.” Progressive taxation “puts the burden on those who can best afford it.”
Trump’s persistent praise for progressive Democrats, especially Hillary Clinton
Perhaps the strongest evidence that Trump is manifestly not a conservative — and not even a Republican — is his dependable history of condemning Republicans and praising Democrats.
In 2004, Trump claimed he identified “more as a Democrat” because “the economy does better under the Democrats than the Republicans.” (RELATED: Obama Economy Flatlines)
“In many cases I probably identify more as a Democrat,” the candidate for the 2016 Republican presidential nomination said on CNN 11 years ago. “If you go back, it just seems that the economy does better under the Democrats than the Republicans.”
In 2009, Trump enthusiastically endorsed then-newly-minted President Obama.
“We have a young, vibrant, smart president who, I think, is going to do a really good job,” he said on Fox News. “And, honestly, he has to do a really good job or this country maybe will never be the same. We had eight years of a horrendous president, a terrible president. You cannot get worse than Bush. And I really believe that Obama will be a great president.” (RELATED: Remember When Obama Was The Messiah?)
Trump despises Bush.
“The way I look at it, he cannot do worse than Bush,” Trump said of Obama on Fox in 2008.
In 2007, the billionaire real estate developer appeared on CNN to blast George W. Bush as “possibly the worst in the history of this country.”
In the same interview, Trump excoriated then-Secretary of State Condoleezza Rice as “very sad” and called Hugo Chavez, then president of Venezuela, “a lot smarter than” Bush. “Chavez is obviously very cunning,” Trump explained. “I mean, beating our president at every step of the game.” (RELATED: Venezuela, Chicago Public Schools Face Toilet Paper Shortages)
In 2008, Trump expressed surprise that then-House Speaker Nancy Pelosi did not attempt to impeach Bush over the 2003 invasion of Iraq. “It just seemed like she was going to really look to impeach Bush and get him out of office, which, personally, I think would have been a wonderful thing,” Trump said on CNN.
In the same interview, Trump praised Saddam Hussein because “he killed terrorists.”
Trump’s hatred for Bush is perhaps only rivaled by his love for Hillary Clinton and Bill Clinton. Trump — along with his wife and children — have contributed more than $116,000 to the Clintons.
Trump has given between $100,001 and $250,000 to the Clinton Foundation. The first of his two wives has contributed between $5,001 and $10,000 to the charity.
At least $11,500 of Trump’s cash has gone to fund Hillary Clinton’s various campaigns for political office.
In 1999, Trump zealously praised Hillary Clinton as “a wonderful woman” in a CNN interview with Wolf Blitzer. “She’s really a very terrific woman,” he gushed. “I know her. She stays in Trump Tower when she’s in New York.”
In early 2007, during Hillary’s first, failed presidential run, Trump predicted that she would be the Democratic nominee. “I think she’s a very, very brilliant person, and as a senator in New York, she has done a great job. Everybody loves her.”
In a September 2008 with Larry King, Trump complained that Obama should have picked Clinton as his vice presidential running mate instead of Joe Biden. “I mean, you know, I don’t understand why Hillary wasn’t chosen because she was really winning,” a puzzled Trump said. “The fact is that Obama went limping across the finish line. He should have chosen Hillary, it would have been a much different race, I believe. Right now, it looks to me like McCain is probably winning.”
Three months later, Trump applauded Obama’s selection of Clinton as his secretary of state nominee. “I think Hillary is a great appointment,” he said. (RELATED: FBI Investigates Hillary Clinton’s Private Email Server Setup At State Department)
Trump’s praise for Democrats extends well beyond the Clintons.
In October 2008, he called Pelosi “a very impressive person.”
In a CNN appearance in 1999, he called Democratic Rep. Charlie Rangel “a terrific guy” who would make an ideal cabinet secretary, perhaps as secretary of state.
In 2010, a special eight-member panel of the House ethics committee found Rangel guilty on 11 ethics charges.
In December 2008, Trump called secret-emailing former Environmental Protection Agency administrator Lisa Jackson “an amazing appointment” by Obama. “I know Lisa Jackson very well because I do a lot of business in New Jersey,” Trump said on CNN.
Trump’s plan for astronomical progressive taxation
In 1999, the Reform Party version of Trump proposed a colossal 14.25 percent “net worth tax” that would have raised taxes by $5.7 trillion. The one-time tax would have soaked all American individuals and U.S.-based trusts valued at $10 million or more.
Trump believed the tax — the cornerstone of his economic plan at the time — would immediately eliminate the national debt. He also aimed to cut taxes on middle-class people and fund Social Security.
Many economists criticized the highly progressive tax plan at the time, pointing out that a tax on investors and wealth creators would likely crater the American economy. “Even talking about it would risk capital flight out of the country,” economist Andrew Hodge told the Associated Press. “It is pretty confiscatory in terms of property rights.”
Mark Zandi, currently Moody’s Analytics chief economist, observed that Trump’s calculations were wrong. The entire net worth of all American households in 1999 was $38.4 trillion, Zandi said. Thus, Trump would need a one-time tax at 14.25 percent of every American man, woman and child and, even then, he couldn’t have reached his target of $5.7 trillion.
Trump insisted that his math was accurate. “The plan I am proposing today does not involve smoke and mirrors, phony numbers, financial gimmicks or the usual economic chicanery you usually find in Disneyland-on-the-Potomac,” he said.
He also asserted that his massive tax on wealth would lead to more economic activity and more investment in new businesses.
Does Trump still favor his massive, punitive tax scheme on wealth? He won’t say. On one hand, as Trump began to flirt with running for president as a Republican in 2011, he began to distance himself from his proposal. He has certainly not made it a cornerstone of his current presidential campaign.
On the other hand, in an August 2015 interview with Sean Hannity on Fox News, Trump seemed to suggest he currently has no philosophical problem with the wealth tax. He claimed the enormous was “a very conservative thing.” (RELATED: Trump On A Wealth Tax: ‘I Think That’s A Very Conservative Thing’)