He also blamed the tax code, claiming many times to have taken advantage of it, and boasting of paying insanely low taxes on his businesses. This was seen as horrible by a lot of the left in this country - proof that "he doesn't want to shoulder his fair share of the burden"- but served as evidence to what a lot of middle America has suspected for years, that the tax increases Democrats proposed to pay for welfare programs weren't effecting the rich and were being paid for by the middle class. (Yes, this is a simplification of the issue.) Trump's 'I broke it and I know how to fix it' approach to the tax code the reason a lot of people who don't trust corporations voted for a tycoon.
Trump won despite his status as a corporate tycoon because the people basically believe he's a double-agent. A corporate tycoon born with the heart of a worker. I think there's an argument that could be made there: Trump has a long history of being looked down upon by high society.
Trump's also credible, because as someone whose attempted many different lines of business, he's seen what it takes to be competitive, and as someone with the heart of a worker, he didn't like it and wanted to even the playing field.
Trump is the epitome of "Don't hate the player, hate the game". Trump was in a very unique position, shared perhaps only by a few dozen other living souls, to see the game, hate it, and be able to make a credible attempt to fix it.
He also blamed the tax code, claiming many times to have taken advantage of it, and boasting of paying insanely low taxes on his businesses. This was seen as horrible by a lot of the left in this country - proof that "he doesn't want to shoulder his fair share of the burden"- but served as evidence to what a lot of middle America has suspected for years, that the tax increases Democrats proposed to pay for welfare programs weren't effecting the rich and were being paid for by the middle class. (Yes, this is a simplification of the issue.) Trump's 'I broke it and I know how to fix it' approach to the tax code the reason a lot of people who don't trust corporations voted for a tycoon.