The Wicked Man Behind the Curtain

Donald Trump and the Wizard of Oz Illusion

I’m on the train home to go see Wicked 2 with my family and I can’t help but reflect on how accurate the original The Wizard of Oz is as a parable of Donald Trump’s American populism. The story’s themes of illusion, manipulation, and false grandeur map so neatly onto our political moment that the parallels practically draw themselves.

The story was first connected to early American populism by Henry M. Littlefield in back in 1964. To Littlefield, Dorothy represented ordinary Americans, the Scarecrow symbolized underestimated but capable farmers, the Tinman stood for dehumanized industrial workers, and the Cowardly Lion mirrored William Jennings Bryan’s blustery but inconsistent leadership. The Yellow Brick Road reflects the gold standard, Dorothy’s silver shoes the “free silver” solution, the Wicked Witches the regional business powers squeezing workers and farmers, the Emerald City the illusion of prosperity in Washington, and the Wizard the politician who rules through spectacle rather than substance.

A quarter into the 21^st century, Donald Trump is that man behind the curtain: selling lies, pushing crypto scams, and bending to the spell of any cruel billionaire for the right price. He is loud, theatrical, and desperately reliant on the belief that no one will dare peek behind the curtain.

The Wizard maintains power by convincing people he alone can solve their problems. Trump pushes the same mythology: that institutions are corrupt, experts are useless, and only he possesses the singular wisdom to fix a broken nation. This is not leadership; it is a cult of personality built on manufactured fear and artificially inflated bravado. And like the Wizard’s contraptions, it functions only so long as the audience doesn’t examine the mechanics too closely.

The Wizard’s subjects don’t question the spectacle because the spectacle is comforting. It simplifies their fears. It externalizes their hopes. The same psychological pull animates Trump’s modern strongman politics. Populist showmanship thrives when people feel disoriented or left behind. It thrives when the performance feels better than the messy truth.

His rallies are staged like arena shows, complete with chants, lights, and exaggerated promises. His public persona is built on hyperbole: the biggest, the best, the strongest, the most tremendous – claims delivered with a confidence that would be comical if they weren’t tied to real-world consequences. Beneath the bluster, however, the curtain hangs precariously. Much of his “strength” derives from a projected image, not from substance.

But, of late, Trump has been on a losing streak from bungling the government shutdown battle, to a blue wave in this year’s recent elections, to his own party turning on him over the release of the Epstein files, to the dismissal of his cases targeting James Comey and Tish James. Just today, a court upheld a ruling against Trump that imposed a $1 million penalty against him for his frivolous lawsuit against Hillary Clinton.

The Emerald City has bowed in awe to Trump for too long. But we must remember – all that spectacle is camouflage – an elaborate stage set to conceal his insecurity and his incompetence. Pull back the curtain, and his power collapses into a puff of smoke.

That’s why I’m so excited to be joining The Siren to work to expose the truth about this administration’s corruption. I’ve spent the last decade working to elect Democrats, communicating key progressive ideas, and battling MAGA trolls on TV. Now, each week I’ll be bringing you a new perspective right here.

Happy Thanksgiving and I look forward to pulling back the curtain with you all!

A little more on my background: Kaivan Shroff is a political commentator and attorney. He also serves as senior advisor to the Institute for Education (a D.C. non-profit), was a 2024 DNC presidential delegate, and worked as a digital organizer on Hillary Clinton’s 2016 campaign. Shroff holds a joint degree from Harvard Law School (JD) and the Harvard Kennedy School (MPP), an MBA from the Yale School of Management and a BA in Political Science from Brown University. He appears frequently on Fox News, CNN, NBC, NewsNation, ABC, and Newsmax to discuss breaking news stories and the 2024 election and has been published in various outlets including the Chicago Tribune, Boston Globe, Huffpost, The Hill, San Francisco Chronicle and more.