To hit him where it hurts, you must go to the root of his appeal. According to Ron Brownstein’s thesis of the 2016 primary, Trump is winning because “the blue-collar wing of the Republican primary electorate has consolidated around one candidate” while the white collar crowd remains hopelessly splintered. So in order to draw blood, you must come up with an attack that can not only speak to white working class voters, but also begin to break Trump’s spell.
A billionaire real estate developer might make for an odd working class political (anti-)hero, but he has always projected the over the top caricature of what a working stiff might think being rich would be like. And his outer borough accent conveys a disarming familiarity that is impossible to fake.
So how do you chip away at this rapport? You start by shattering the illusion that Trump is a friend of the little guy. To his credit, Trump possesses an uncanny ability to perceive, identify, and harness the wants and needs of the average Joe. The problem is that Trump takes this unique insight into the working class and exploits it for his own gain.