People like Trump because they think he’s successful and that, to borrow from The Donald himself, everyone who’s spent their career in politics is a loser who couldn’t cut it in a real rough-and-tumble environment like, say, the real estate business. And if Trump weren’t right about this, after all, why would NBC have hired him to fire people on The Apprentice? 

Whoever wants to take down Trump will need to get more voters believing that Trump is only successful in the branding and self-promotion department, and rather fair-to-middling in all the others entailed in running a thriving business. They don’t need to view him as a failure; they just need to come to view him as substantially less of a winner than they do now.

This will be a pretty major feat, but it is doable. According to CNN Money, “no major US company has filed for Chapter 11 more than Trump’s casino empire in the last 30 years.” 

In order to pay creditors, he has had to give up everything from yachts to airlines to his stake in hotels. The 2004 bankruptcy seems to have stemmed from excessive debt. It’s not hard to speculate that Trump-inclined voters might have reservations about electing a guy with that particular blemish on his record given their likely worries about the size of the national debt.

A bonus to pulling it off is that The Donald tends to fly off the handle and say over-the-top things when his business record is criticized. That is a Trump characteristic that we know Republican primary voters, including those who are otherwise Trump-favorable, are concerned about.