Eleanor (Eliza Scanlen) is portrayed returning from a progressive education in London, where she learned about self-discovery and sex from a lesbian mentor. Forced into a "dreaded" societal debut in New York, she feels insecure and "plain" until she reconnects with her ambitious cousin, Franklin D. Roosevelt. Her story highlights the tension between her progressive values and the rigid expectations of her high-society family.

Portrayed by Eliza Scanlen in her younger years, Eleanor reluctantly ends her progressive education in London to return to New York. The episode captures her dreaded societal debut, where she reconnects with her ambitious cousin, Franklin D. Roosevelt (Charlie Plummer), marking the start of their historic partnership.

But she doesn’t. The next afternoon, standing before two hundred women in a union hall, she deviates. She talks about the right to organize. About the women whose husbands beat them when the mines shut down. About the air they breathe—black and thick and wrong.

Jayme Lawson portrays Michelle Robinson as a determined attorney at a Chicago law firm. Her life changes when she is assigned to mentor a charming, idealistic summer intern from Harvard Law named Barack Obama (Julian De Niro). Key Cast and Production