Trotter’s Early Years

William Monroe Trotter was born on April 7, 1872, during Reconstruction, and came of age during the Jim Crow era. Trotter’s father, James Monroe Trotter — a well-respected lieutenant in the Union Army — instilled in his son a deep sense of race pride.

But as Greenidge recounts, James also raised his son with an iron fist. When a six-year-old William was attacked by a group of white boys who called him a “white n*gger” — alluding to Trotter’s light complexion — James’s response was to beat his son, rather than comfort him. His reaction was meant to convey a valuable lesson: Trotter needed to stand up for himself and refuse to allow white people to mistreat him. This painful experience crystallized Trotter’s early views on race and black resistance to white supremacy.

In some ways, then, it is not surprising that Trotter came to reject the politics of Booker T. Washington, founder of the Tuskegee Institute in Alabama. Washington’s ideas of racial uplift, self-help, and social activism enjoyed much currency among many black activists, including Garvey, who credited the Tuskegee founder for inspiring his decision to become a “race leader.” Washington’s influential 1901 autobiography Up From Slavery, which emphasized the significance of black education, had a profound effect on “race leaders” — and those who aspired to be race leaders — in the United States and across the diaspora.

Trotter, however, eschewed Washington’s accommodationist, conservative views. “For Monroe Trotter,” Greenidge explains, “who never had to walk five hundred miles for an education that valued his physical labor over intellectual and political engagement, Booker T. Washington’s conservatism was anathema to his family’s proud history of black agitation for racial justice.”

Harvard Years

After graduating from high school, Trotter enrolled at Harvard University. Despite the challenges associated with being black at a predominately white university during the early twentieth century, Trotter thrived at Harvard. According to Greenidge, he was “undeniably popular and respected amongst his black and white friends.” During his four years on campus, Trotter expanded his social networks and built meaningful relationships with a cadre of “Harvard men,” including his teacher Dr George Franklin Grant, the first black instructor at Harvard, and fellow student W. E. B. Du Bois. Trotter earned excellent grades and “never ranked lower than third in class.” In 1895, he graduated from Harvard as the first black Phi Beta Kappa.

Trotter’s success, however, could not shield him from the harsh realities of what it meant to be black during the twentieth century. Trotter’s race, combined with his radical politics, blocked him from finding long-term employment after graduation. And, solely on principle, he balked at the offer that came his way to teach at a black school in DC. As Greenidge writes, “[Trotter] refused to live and work in a segregated environment so far South.” After going from job to job, he finally landed a permanent position in real estate in 1896.

With his newfound financial security, Trotter began pursuing a romantic relationship with Geraldine “Deenie” Pindell, a childhood friend whose background and political commitments aligned well with his. Pindell, who was also light in complexion, was raised in a black family that adopted a radical stance against racism and became a social activist in her own right. She supported Trotter’s efforts to launch the Guardian in 1901 and helped manage the paper’s finances. Two years later, when Trotter was jailed during the Boston Riot, Deenie ran the newspaper in his absence. During this period, she also advocated for the release of William E. Hill, a black veteran who had been wrongly convicted.

“Forever on the Firing Line”

The Guardian provided an important outlet for black radical activism and a crucial platform for Boston’s black working class. “We have come to protest forever against being proscribed,” Trotter explained in the first issue, “or shut off in any caste from equal rights with other citizens, and shall remain forever on the firing line at any and all times in defence of such rights.”

Although the paper circulated widely among Boston’s black residents of all social classes, Trotter envisioned the Guardian as an outlet to speak directly to working-class black people and address the issues that concerned them most. To that end, Trotter centered the political demands of working-class black voters who were otherwise overlooked by politicians. In 1902, for example, Trotter printed the demands of local black citizens in the Guardian after Republican senator Henry Cabot Lodge ignored them. He also appealed to readers to punish local Republican candidates at the ballot box if they refused to listen.

Trotter’s response exemplified his unwavering support for the black masses. Unlike many of his middle-class and elite contemporaries, Trotter rejected the paternalistic notions of racial uplift ideology. Greenidge writes that instead of “prescribing conservative uplift to make the black masses ‘respectable enough’ for white consideration, Trotter immersed himself in the lives of the working, yet culturally and politically conscious, masses as a way to implement radical racial uplift.”

His efforts did not go unnoticed. Black workers in the city extended their support for Trotter and played a key role in the Guardian’s success. They read the paper, attended its events, and sold copies in their communities.

Confrontational Politics

One of the most striking features of Trotter’s politics was his confrontational style of leadership. The world caught a glimpse of it when he publicly challenged President Woodrow Wilson in November 1914.

Trotter, like other black radicals during this period, had long been at odds with Wilson because of his poor record on race and civil rights. Yet Trotter was interested in speaking with Wilson — in what would be their second meeting — in hopes of convincing the president to end his segregationist and racist policies.

In an infamous gathering with fellow activists in the Negro Independent Political League, the black radical called out Wilson for his racism in a heated exchange. “Only two years ago you were heralded as perhaps the second Lincoln,” Trotter declared, “and now the Afro-American leaders who supported you are hounded as false leaders and traitors to their race.” “Have you a new freedom for white Americans and a new slavery for Afro-American fellow citizens?”

Wilson took issue with Trotter’s tone — perhaps more than the accusation of racism. “If this organization wishes to approach me again, it must choose another spokesman,” Wilson curtly explained. But Trotter had no interest in sugarcoating his message.

That decision increased his many admirers in the black community, who applauded his strong stance against white supremacy. In other ways, however, it would cost him. While many viewed the Trotter-Wilson imbroglio as evidence of a passionate activist’s commitment to his people — a commitment that fueled his decision to lead a 1915 protest attempting to ban the filming of Birth of a Nation in Boston — Trotter faced harsh critique among fellow black elites.

Trotter’s mounting personal issues and financial challenges compounded these realities. In October 1918, Deenie died of the flu, and Trotter battled his own string of health issues. Amid the pain and turmoil, Trotter managed to attend the 1919 Paris Peace Conference, where he expressed his support for African liberation struggles. Still, it was clear to those around him that his political work was gradually coming to an end.

A Lasting Legacy

When the Great Depression hit following the 1929 stock market crash, Trotter quickly found himself with few people in his circle as he fought impending bankruptcy and the newspaper’s steady decline. The personal and professional losses took a toll on his psyche. Greenidge recounts that by the early 1930s, Trotter could hardly look at his own sister “without pacing the floor incessantly.” The weight of the world was on his shoulders.

For Trotter, the arrival of his sixty-second birthday on Saturday, April 7, 1934 was no reason to celebrate; it only intensified the pain and anguish he felt. During the wee hours of the morning, Trotter decided to end his life.

What Trotter could not have foreseen is that for all of his perceived failures, he had left a mark that would shape the future of black radical politics. He had agitated for the rights and dignity of black people, denounced white supremacy without hesitation — and in the process, inspired generations of black activists.

By telling Trotter’s story with care, precision, and analytical depth, Greenidge has restored Trotter’s important place in black radical history. If Trotter’s impact has been overlooked by mainstream audiences, then the publication of Black Radical might symbolize a turning point. This superb book gives William Monroe Trotter his due, reclaiming the Guardian editor as a towering and influential figure in black radicalism in Boston and beyond.