The protagonist is a young, unnamed African American nomenclature consultant living in New York City. He possesses a rare talent for creating highly successful brand names but has retreated from society following a severe toe injury that left him with a psychosomatic limp. Emotionally closed off and isolated, he approaches the world primarily through the lens of marketing and branding, preferring to observe rather than actively participate in life.

Regina is the first African American mayor of Winthrop and a descendant of one of the town's founding families. Elegant and professional, she cares deeply about status, appearances, and upward mobility. As a member of the town council, she strongly advocates renaming the town to "Freedom," the name originally chosen by her ancestors when they first settled the area.

Lucky is a white software entrepreneur and an influential business leader in Winthrop. A fast-talking salesman, he represents modern commerce and is heavily invested in the town's rebranding efforts. He wants to rename the municipality "New Prospera" to attract new residents, using consumer culture to erase the area's complex past in favor of a profitable future.

Often called Albie, he is an eccentric older man with white hair, typically seen wearing faded jogging suits. He is the last heir of the wealthy Winthrop family, whose ancestor built the town's barbed wire factory. He owns the mostly empty Hotel Winthrop and wants the town to retain its current name to preserve his personal heritage.

Roger is the protagonist's former boss at the nomenclature firm. Like the protagonist, he is an alumnus of the fictional Ivy League school Quincy, benefiting from an old boys' club mentality that facilitates professional favors.

Muttonchops is an ornery African American bartender working at the hotel. As a descendant of one of the town's original families, he maintains a skeptical view of the council's rebranding efforts, arguing that changing a place's name does not alter its true character.

Beverly is the town librarian who assists the protagonist with his research. She provides him with crucial, unredacted historical information regarding the town's founders and the political maneuvering that originally led to its current name.

Jack is a prospective homebuyer visiting Winthrop. Drawn to both the town's tradition and Lucky's vision for its future, he represents a wave of new residents looking to buy affordable property in gentrifying neighborhoods.

Dolly is Jack's wife and a participant in the Help Tour. She is part of the demographic of young families scouting Winthrop for its amenities and potential as an up-and-coming area.

Bridget is a woman the protagonist dates during his time at the nomenclature firm. She experiences the immediate aftermath of his physical deterioration following a disastrous team-building weekend.

Abraham is Regina's ancestor and a leader among the freed slaves who settled the town in 1867. Known as "the Light," he was an optimistic, preacher-like figure who sought to form alliances and originally named the settlement Freedom.

Field is an original town founder who lost his family during slavery. Cautious, distrustful, and highly realistic, he was known as "the Dark." He serves as a historical counterpoint to Abraham Goode's optimism and warned against trusting outsiders.

Sterling is Albert's ancestor and a late-19th-century tycoon who made a fortune manufacturing barbed wire. He leveraged his economic power to establish a factory in the town, trading jobs for the right to rename the municipality after himself.

Abigail is an ancestor of Regina whose diary recorded "The Lost White Boy" anecdote. Her writings document the original settlers' perilous journey and the constant threat of violence they faced before founding the town of Freedom.

White Jimmy is a light-skinned African American man traveling with the freedmen in the 1860s. He attempted to safely return a lost white child to a nearby settlement, an act that inadvertently brought a violent mob down upon his camp.