Cortelyou reluctantly agrees to manage Roosevelt’s 1904 reelection campaign. Despite his reputation for integrity, he becomes the target of press attacks for accepting large donations from big businesses. Tensions rise when Cortelyou, offended by the President’s insinuations, pointedly reminds him: “Everything you write down goes to history.” Meanwhile, Roosevelt’s daughter Alice marries a prominent politician who is 15 years her senior. The wedding, held at the White House, draws hundreds of the nation’s elite and becomes the most celebrated social event of the year.

Lilly Cortelyou and Edith Roosevelt’s shared concerns over immigration policy reach a breaking point when Edith visits Ellis Island and witnesses the harsh, invasive questioning of female immigrants by male officials. At the time, Ellis Island served as America’s primary federal immigration processing center from 1892 to 1954 - the first stop for more than 12 million hopeful newcomers seeking a fresh start. Meanwhile, Cortelyou’s own journey takes a dramatic turn. Once a humble postal clerk, he rises to become Postmaster General and launches an ambitious effort to modernize the nation’s aging mail system. He champions the introduction of automobiles to speed delivery and takes a struggling young clerk under his wing, offering him a second chance.