Teaching Gatsby Under Obama Was Eerie. Teaching It Under Trump Is Crushing

My lesson has turned from an academic contemplation of Fitzgerald’s poetry and politics to a bitter reflection on the cruel realities of power.

When I started teaching F. Scott Fitzgerald’s The Great Gatsby to my high school sophomores several years ago, I couldn’t shake a sense of creeping déjà vu ― the sense that I had seen it, heard it, lived it all recently. Finally, it hit me: Jay Gatsby reminded me of Barack Obama (or, I suppose, vice-versa). Not so much in their characters or actions as in their stations and the narratives that circulated around them. 

I soon discovered that I was not the first to see parallels: James Gatz’ quick rise from obscurity, his contested record at Oxford University, and his connection to Meyer Wolfsheim all seemed to presage the controversial trajectory of Barack Hussein Obama, from Harvard Law to community activism with folks like Bill Ayers and Jeremiah Wright, to a one-term senator from the most infamously corrupt city in the nation, to, unimaginably, President of the United States. In the space of a few years, Obama went from being the man with a name that could never win in America to being the occupant of the greatest palace in the land. And, like Gatsby, he attracted the attention of not a few privileged persons who decried his fitness as America’s first citizen. 

Over the course of his two terms, President Obama stood up against tests of forbearance that would have broken no small fraction of his predecessors. The birther conspiracies; the slights on his education; the associative allegations of radicalism, reverse racism, and crime; the accusations of vast, organized voter fraud ― all of it was crafted to delegitimize his presidency, to convince the American public that he was nothing more than a confidence man who had risen above them with smiles, style, and sweet platitudes that allowed us to believe what we wanted to believe about ourselves: that we were the kind of nation where the mixed-race son of a broken family with middle-class roots could float above our larger, societal brokenness and remind us all of what was possible.

In Fitzgerald’s novel, when Tom Buchanan gets suspicious of his up-and-coming neighbor, he attacks Gatsby in the very arteries that carry the lifeblood of upper-class legitimacy: Gatsby is “Mr. Nobody from Nowhere,” an imposter whose reputation as an Oxford man is belied by his unorthodox pink suit, a bootlegger and a swindler whose proper place is bringing groceries to the back door of mansions like the one Tom and Daisy inhabit. He is a fraud who “[sneers] at family life and family institutions” (such as white supremacy).

In another fiction, Obama is the foreign-born son of a disreputable Kenyan and an unsteady divorcée, a slick-talking political agitator who conned his way into and through Harvard Law School before returning to the riffraff and radicals who propped him up in Chicago. He is a secret Muslim who winks at drugs and trades in arms and sympathizes with terrorists while waging warfare on family life and institutions through redistribution economics and the legalization of gay marriage. 

There is no greater proponent of this narrative than Obama’s successor, who rose to political fame by demanding, then doubting, Obama’s birth certificate. Trump attacked Obama at every turn, calling for his resignation and deriding him publicly for positions that Trump himself would adopt in the first 100 days of his administration. Trump’s insistence on Obama’s otherness can only be fully understood as a complement to Trump’s own appeal to voters: “Believe me.” Trump, whose checkered history of bankruptcies and lawsuits, sexual allegations and public vulgarity, insubstantial strategy and nonexistent policies make Obama’s eight scandal-free years look like a storybook presidency—this man asks us to trust him when he says Obama is not one of us.

And we do it. 

Why? For the same reason that no one thinks to ask Tom Buchanan why he’s so upset over the death of Myrtle Wilson: he is so clearly one of “us.”

In Obama’s second term, it was possible to read Fitzgerald’s novel with a kind of steely-eyed optimism. Sure, Tom and Daisy abscond, pinning Myrtle’s death on Gatsby. Yes, the aristocrats are unscathed by their brush with scandal and tragedy, leaving the poor and the nouveau riche to squabble and kill each other. But as long as Obama sat in the Oval Office, it was possible to rest in the confidence that our own come-from-nothing celebrity president had triumphed not just once, but twice, over the Buchanans of the world. Perhaps, America had learned something from Gatsby and had finally shed the old rules that kept power concentrated in the same hands generation after generation. Perhaps that green light, that “orgastic future” that eluded so many before us was finally within our grasp.

On the morning of November 9th, 2016, we awoke to the realization that, like Gatsby’s fantastic parties, our dream turned out to be no more certain than “a rock on a fairy’s wing.” It has been one long hangover since then, and teaching The Great Gatsby has turned from an academic contemplation of Fitzgerald’s poetry and politics to a bitter reflection on the cruel realities of power. It is impossible not to read the scene of Gatsby’s death and feel desolate as Obama’s legacy erodes like a castle in the sand. It is impossible to watch Trump slide through the fingers of the law and public decorum and not be reminded of the Buchanans, who elude the consequences of three aggravated deaths as easily as they pack their suitcases. If, before, we read Gatsby without feeling hopeless, it was because we could hide from the injustices of the book by pointing to the man who rose to power on a message of hope. Today, we do not have that luxury.

Is The Great Gatsby a book for the Trump Era? Is its pessimism too bleak for our own future, which might be reclaimed with some determination and grit? Might not a younger generation be better served by a call to arms than by a poetic plaint for the American Dream? 

Perhaps so, but this also is true: The greatest risk we currently face is slipping into autocracy, in which the powerful can manipulate truth with impunity. This has already begun. As long as there exists the opportunity to challenge the dominant narrative, there is hope for truth, and perhaps even justice. When, by its force or our acquiescence, the dominant narrative becomes the only narrative, then the light of truth retreats beyond our view. Gatsby is a novel that questions the storied glitter of the roaring 20s, peeling back the gold leaf to find the rot lurking underneath. 

We need minds who can peel back the leaf on our own gold-plated present. And until that process is complete, I’ll push through my own feelings of cynicism and keep Gatsby in my classroom. Perhaps next time, we will teach our children better, push back on power harder…. “And one fine morning—”