—Barrington Williams, B1Daily

American politics loves winners. It rarely remembers those who ran simply because they believed they had the right to be there. Isabell Masters belongs to that forgotten class of political figures—people whose persistence, not their vote totals, changed history.

A Black American educator, single mother of six, and political outsider, Masters ran for public office repeatedly when the system gave her every reason not to. She ran for president five times, more than any woman in U.S. history, not because she expected victory, but because she believed representation was not something to wait for—it was something to claim.

An Educator Before Anything Else

Masters’ political life was rooted in education. Born in 1913, she dedicated decades to teaching across the country, working in classrooms in California, New York, Kansas, Nevada, and beyond. She believed education was the foundation of democracy and spent her life reinforcing that idea in both word and action.

Her commitment to learning never stopped. Even later in life, she pursued advanced degrees, ultimately earning a doctorate in her late 60s. At a time when Black women were routinely denied professional and academic advancement, Masters insisted on intellectual authority as a form of resistance.

She raised six children as a single mother while building a career—an experience that shaped her understanding of government not as abstraction, but as something that directly affected real families.

Running Without Permission

Masters entered politics without party backing, donors, or media support. She created her own political vehicle—the Looking Back Party—not to build a lasting institution, but to ensure she could access the ballot.

Her presidential runs spanned two decades:

• 1984
• 1992
• 1996
• 2000
• 2004

She ran during an era when Black women were virtually invisible in national politics, long before conversations about diversity or representation reached the mainstream. Each campaign was a declaration that the presidency was not the exclusive domain of white men or political dynasties.

In some elections, she managed ballot access in a handful of states. In others, she ran as a write-in candidate. Her children often served as her running mates—an unconventional choice that underscored the deeply personal nature of her political mission.

Symbolism as Strategy

Critics dismissed Masters as symbolic, unserious, or quixotic. But symbolism was the point.

At a time when Black political participation was still met with hostility, her repeated presence on ballots challenged the psychological barriers of American elections. She made visible what the system preferred to keep abstract: that Black women could aspire to the highest office in the land, even without permission.

Her campaigns were not about winning power. They were about normalizing presence.

Beyond the Presidency

Masters did not confine her ambitions to the White House. She also ran for local offices, including city council and mayoral positions, believing political engagement mattered at every level. These runs reinforced her belief that democracy was participatory, not hierarchical.

She understood that change often begins locally, but visibility at the national level reshapes what people believe is possible.

A Legacy of Persistence

Isabell Masters never won an election. Yet her legacy is secure.

She expanded the idea of who could run, who could speak, and who could be taken seriously—simply by refusing to stop. Her five presidential campaigns remain unmatched by any woman in American history, a record born not of ambition, but of insistence.

Masters lived to 98 years old, long enough to see Black women begin to enter national politics in greater numbers. The path they walked was not created overnight. It was cleared by figures like Isabell Masters—women who stood at the ballot box year after year and refused to be erased.

In a political culture obsessed with victory, Masters reminds us that sometimes the most radical act is showing up again.

—Barrington Williams, B1Daily