Interpreting America: Teaching The Great Gatsby to SAR Juniors

When I shared my excitement about teaching The Great Gatsby to my eleventh-grade American literature classes as a new teacher at SAR, my friends and family recalled learning about flappers, the imagery from Gatsby’s iconic parties, and other symbols of Jazz Age excess. Many noted the timelessness of the narrator’s famous criticism of the upper class in his characterization of Tom and Daisy as “careless people.” While no one mentioned anything about race in the novel, I knew that I wanted to weave in conversations about the brief yet significant moments when race emerges explicitly. The main motivation behind my choice was my broader, yearlong goal to encourage students to consider their own ethical and civic responsibility as Jews within the wider fabric of America. As Modern Orthodox teenagers, SAR students live in two overlapping worlds. On one hand, they belong to a minority community whose daily lives are shaped by distinct rituals, values, and norms. On the other hand, they are coming of age within the civic arena of the United States, where questions of race and racial identity remain deeply significant. As these students approach young adulthood, they will be increasingly called upon to navigate and shape national discourses on identity in ways that advance justice and dignity for all people.

I believe that the English classroom, particularly the American literature classroom, is one of many great places for students to develop confidence in taking on this role. The American stories we study are not static artifacts; they emerge from specific historical contexts, and yet the discussions they raise about power imbalance, exclusion, and the promises and failures of the American dream for minorities are timeless and relevant to SAR’s student body. This is especially true in The Great Gatsby, where racialized depictions of Black and Jewish characters intermingle. Therefore, I saw our unit on this novel as an opportunity for students to grapple with how histories of antisemitism and antiblack racism differ yet also coexist within the American narrative, and to consider what that reality demands of them as participants in that story.

One of the most striking patterns that emerged in our discussions was students’ careful balancing of their sensitivity to injustice with their emphasis on historical accuracy. For example, when analyzing Meyer Wolfsheim, a Jewish figure who is based on Arnold Rothstein, a man who allegedly fixed the 1919 World Series, some students initially reacted by condemning the narrator, Nick, who repeatedly references Wolfsheim’s nose and the character’s association with corruption. However, some students questioned whether we were approaching the text incorrectly; perhaps Nick’s language reflected mainstream 1920s discourse about Jews, and while it rightfully offends us now, it would be unfair to characterize Nick as uniquely antisemitic. This spirited yet respectful debate culminated in a reflection on the practice of ethical reading, which students concluded entails naming the harm inflicted by racist stereotypes while also inquiring  about authorial intent and historically specific norms. Students also spoke about Fitzgerald’s depictions of Wolfsheim in relation to their own concerns as Jewish Americans, noting that even today, Jewish achievement is often framed through stereotypes that associate Jewish success with corruption and conspiracy.

These discussions about antisemitism in the novel created a natural opening for a broader conversation about Fitzgerald’s depiction of racial minorities. In particular, students were attentive to Nick’s racialized depictions of Black Americans. Nick initially presents himself as a non-judgmental person who is aware of social injustices and the reality of class privilege. However, his descriptions of Black Americans reveal prejudices, as when he observes, while driving to New York City, “A limousine passed us, driven by a white chauffeur, in which sat three modish Negroes, two bucks and a girl. I laughed aloud as the yolks of their eyeballs rolled toward us in haughty rivalry.” I had students read the passage without much context besides the fact that the eyeball imagery echoes racist minstrel iconography. Students strongly disapproved of Nick’s dehumanizing language and mocking tone. However, some wondered whether their modern sensibilities may be misaligned with those of even socially conscious individuals in the 1920s. Some students then countered that presentism is not always to be feared, as viewing texts from our own historical perspective can reveal meanings that might otherwise be overlooked. One student noted that, as a historically persecuted group, it is our duty to stand up for other minorities, and that means condemning racism regardless of one’s intent. This comment led students to consider how critiquing depictions of race in novels from the past is a political act that affects how we confront injustice in the present.

Focusing on representations of race in The Great Gatsby with my students underscored that they see the stakes in their roles as interpreters of great works of literature. My students recognize that they should not strive to be detached observers of facts; they embrace the challenge of bridging their modern ethical concerns with knowledge of historical context so texts can speak their truths and serve as tools to question power and reckon with the legacies we inherit. Students also reflected meaningfully on what it means for them, as Jewish students living in 2025-2026, to encounter antiblack racism. They spoke about the importance of avoiding conflating diverse experiences and celebrating the intersectionality within the Jewish community, as well as how American literature often reveals overlapping themes in its depictions of Jewish and Black Americans, particularly around the search for belonging and cultural survival in the face of exclusion and the pressure of assimilation. Ultimately, engaging with these intertwined histories reinforced for students that their approach to representations of racial difference in literature is tied to their moral obligations as members of a diverse democracy.

Finally, during these discussions, my students engaged in meaningful dialogue that did not necessarily lead to a monolithic consensus but produced a form of intellectual community in which disagreement could coexist with mutual respect. In an era of increased political polarization and a troubling decline in civil discourse on college campuses, among other settings, I hope that my students can use lessons from this unit to act as leaders of constructive discourse in high school and beyond, not necessarily to enforce conformity in thinking but to encourage respectful listening across lines of difference.