In 1999 and 2000, he considered a bid for the nomination of Ross Perot's Reform Party, which was at the height of its influence after Jesse Ventura won the Minnesota governorship in 1998 as a Reform candidate. Trump's big idea was a one-time wealth tax of 14.25 percent on all individuals and trusts with a net worth in excess of $10 million. The proceeds would be used to wipe out the national debt, with the savings in interest payments going to shore up Social Security and pay for middle-class tax cuts. This is a totally insane idea for a whole variety of reasons, many of which Bruce Bartlett ran through in the Wall Street Journal at the time. The tax wouldn't raise nearly as much as Trump thought it would, it'd encourage massive evasion, and it'd force huge sell-offs of stock and other assets, leading to, as Bartlett writes, the "liquidation of thousands of businesses."
The wealth tax isn't the only left-wing proposal Trump has flirted with over the years, either. He also used to be a fan of Canadian-style single-payer health care.
"We must have universal healthcare," wrote Trump. "I'm a conservative on most issues but a liberal on this one. We should not hear so many stories of families ruined by healthcare expenses."
The goal of health care reform, wrote Trump, should be a system that looks a lot like Canada. "Doctors might be paid less than they are now, as is the case in Canada, but they would be able to treat more patients because of the reduction in their paperwork," he writes.