For Trump, why bother tossing and turning over your countless investors left holding your bag, many of whom were the pension funds and 401Ks of the same middle class workers he's promised to "make America great again" for.
The self-proclaimed "greatest jobs president God ever created" had his most recent bankruptcy in 2009 when Trump Entertainment Resorts went belly up and 1,100 workers were laid off while lenders lost over $1 billion. But on the bright side, since Trump "isn't representing other people," the fates of his workers weren't really his problem.
Just like Mitt Romney infamously adored "being able to fire people who provide services to me," the Donald liked sprinting out of his burning buildings first; if other people bit the dust, well that's just the price of bad smoke detectors.
This by no means implies Trump is Gordon Gekko to Hillary Clinton's Mother Teresa. Quite the contrary; Clinton has very little meat on the bone as far as supporting or pushing legislation that's helped average workers, while supporting many of the poisonous pieces of legislation that's crushed the middle class (i.e. NAFTA).
Both are awful choices without genuine concern or connection for the average Joe; it's just one's social Darwinism is more obvious.
Of course, Trump changes the character he's playing often—sometimes mid-sentence—so he sang a different tune during the first Republican debate, saying he leveraged the laws of this country to do a "great job for my company, for myself, for my employees, for my family."
And there lies the rub. For all the valid and reasonable worries over Trump's immigration hysteria and xenophobia, he's not just a threat to those who look or speak different.
He's a false flag raising hope to those that look like America did from the 1950s through the 70s: the roll-up your sleeve workers who believe Donald Trump will take actions in the White House with only their revival in mind.
He might—as long as it benefits him. In the end, Trump's just pulling the strings of millions of struggling and frustrated workers supporting him. Kind of like the corporate puppets, such as Jeb Bush and Hillary Clinton, he's railed against to come within an inch of the White House.