Becoming White: The Rosenbaum Brothers Portrait

The following was written based on an interview with Rachel Chavkin conducted in October of 2025. 

A portrait of two young boys hangs on the wall of the house on stage. In matching black velvet suits with wide white collars, Ted and Bud Rosenbaum stand hand in hand. Behind them, a grassy pasture rolls into dark forest. The portrait is large, life-sized even, painted in oil, and was costly for the boys’ family to commission in the 1920s.1 Beyond its role as a treasured family heirloom, this painting marks a pivotal moment in Rachel Chavkin’s family history and in her own understanding of identity. Rachel describes this image as a representation of the moment her immigrant Jewish family became known as white.2

Rachel’s grandfather, David (“Bud”), and his brother Ted were the first of their family born in the United States after their relatives emigrated from Eastern Europe. In the final years of the 19th century, their father and four uncles, Harris, Lou, Hymie, Meyer, and Sam, passed through Ellis Island where each was assigned a different last name as they entered the country. The family settled in New Haven, Connecticut, where they opened Rosie’s Tutoring School to serve “the dumb gentile boys at Yale.” The name of the tutoring school reflected the family’s need to bury their Judaism under a generic moniker. Eventually, the brothers opened the Milton School, a boys’ preparatory school. Yet none of the five brothers ever served as headmaster of their own school (or, as Rachel put it, “none of them would actually ever become headmasters … because who would want to send their child to a school that a Jew ran?”). This culture of antisemitism was so powerful that it fostered within the family an internalized antisemitism, one whose onset post-immigration was swift and may well have contributed to the relative success of the family’s school. Rachel’s great grandparents unknowingly marked this period of fleeting financial comfort and aspiration between immigration and the Great Depression when they commissioned the portrait of their sons. 

For Rachel, the painting is more than a family artifact. “It’s a snapshot of the moment that my family claims its entitlement to white privilege,” she says. The way the boys are dressed — family interpretations range from little lords (her mother’s description) to pilgrims (Rachel’s own) — and the very act of spending a large sum on an oil portrait of children were expressions of an aspiration toward whiteness. In a society that offered social and economic access and mobility based on how one appeared, this image helped the family visually distance themselves from a Jewish identity that had the potential to be socially and economically limiting. 

Rachel didn’t always see the painting this way. Over years of creative, and often prompt-based exploration, she began to look at the portrait anew. The TEAM makes theatre through a highly iterative, collaborative writing process that is often driven by prompts during the early phases of writing. Prompts can be offered to the full company or exchanged between individuals, and dozens, sometimes hundreds, are posed and answered over the course of creating a piece. Material that resonates most deeply with the group is returned to repeatedly and ultimately incorporated into the script. In this way, The TEAM’s writing process is consensus-driven.

One such prompt, posed specifically to white-identifying members of The TEAM, asked the artists to trace white supremacy through three generations of their family. In responding to this prompt, Rachel shared the story behind the painting of Bud and Ted. As collaborators returned again and again to this moment in Rachel’s history, and to the enormous oil painting of young Jewish boys dressed like Pilgrims, the collective’s desire to include the painting in RECONSTRUCTING became clear.3  Through this repeated reflection, the painting emerged not only as a personal family artifact, but as a compelling symbol of how families in the United States have sought, and continue to seek, to materially distance themselves from anything perceived as not white and to align themselves with a more socially accepted and recognizable vision of whiteness. This kind of deep, reflective, and honest work helped Rachel trace the role of whiteness in her own family lineage and to see the portrait as part of broader racial and cultural phenomena in the United States.

It was deeply necessary for the white members of The TEAM to undertake the work of identifying and interrogating the ways white supremacy existed within and shaped their families’ histories, and how it continues to reverberate in the present day. As Rachel explains, creating a theatre work about the possibility of intimacy between white and Black people requires that the stakes for the white participants be as high as, or as close as possible to, the stakes for the Black participants, however impossible that parity may be within the culture of the United States. The vulnerability and honesty required to engage in this kind of reflection are essential to any attempt at intimacy. As Rachel reflected, RECONSTRUCTING “has demanded that the white artists have more, and I think people have deliberately used these words, skin in the game. The journey to that demand was emotional.” It was a journey in which collective and personal histories melded, as each artist brought forward their family lineage and stories to explore what might emerge through their interweaving to create something new.

The work is hard but promises the possibility of redemption and even healing, Rachel shared. “My call to, and ultimately my capacity to, articulate the painting’s meaning in the context of RECONSTRUCTING has actually let me love it more wholly and less ambivalently. [It has] let me hold [the portrait] in all of its complexity… My love for the painting and thus my family has significantly deepened because of the opportunity to examine my identity and my family’s identity within this piece… There is such a resilience and a release that comes from looking at and owning [our] stories. [They] become bearable through talking about [them] with community.”

  1. The real painting lives in the Brooklyn home of Rachel Chavkin, Director of The TEAM. A reproduction was made for RECONSTRUCTING. ↩︎
  2. Rachel encountered the phrase, “those of us who have come to be known as white” during a 2017 workshop at the People’s Institute for Survival and Beyond. This phrasing of the cultural and historic phenomenon of becoming white in the United States was impactful for Rachel. ↩︎
  3. In an earlier iteration of RECONSTRUCTING, the painting and the story of the Rosenbaum brothers was included in the script. The painting is no longer referenced in the script but is still part of the set. ↩︎

Photo credit: Julieta Cervantes