The mustache had to go. A classic nineteenth-century handlebar, it was far too recognizable, so William Monroe Trotter shaved it off. In addition to the disguise, he arranged to take a cooking class in his boarding house, evincing a sudden interest that would have surprised his wife, mother, and two sisters. Then he spent six weeks skulking around New York, searching for a ship that would hire him, finally finding work as a scullion on a small steamer headed across the Atlantic. Seaman’s papers carried him as far as Le Havre, where, to his dismay, the captain informed him that crew members were not allowed to disembark, so he devised a ruse that involved delivering a letter to shore. Once there, having left all his possessions behind and still dressed in his cook’s outfit, he went looking for a train.

The year was 1919. Trotter was one of eleven delegates who had been elected by the National Colored Congress for World Democracy to carry the concerns of African-Americans to the Versailles Peace Conference, only to have Woodrow Wilson’s Administration deny them passports. That did not stop Trotter—not very much stopped Trotter—and, alone among the eleven, he made his way to Paris. His subterfuge-filled travels took so long that he arrived after the treaty terms had been dictated to the Germans, but still in time to try to dictate some terms of his own. He was there to let “the world know that the negro race wants full liberty and equality of rights as the fruit of the world-war.” He offered the press corps an account of a recent lynching in Missouri, described the segregated conditions and the discriminatory treatment of black troops, and distributed copies of the demands of the Colored Congress to diplomats at the conference.

Trotter was already a well-known advocate for the cause of civil rights, having published a weekly newspaper in Boston for nearly two decades, but his adventures abroad made him into something of a folk hero. In “Black Radical: The Life and Times of William Monroe Trotter” (Liveright), the historian Kerri K. Greenidge suggests that Trotter’s time in Paris was typical of his activism, in that it was simultaneously a terrific success and a tremendous failure. On the one hand, dozens of newspapers carried reports of his presence at the conference and reproduced the grievances that he brought before the attendees. On the other, his detractors denied, “fake news” style, that he ever even made it to France, and none of his demands were included in the peace treaty. He also ran out of money so quickly—exhausting the three thousand dollars he had received from around the United States in donations as small as fifty cents—that he had to wait another two months for his supporters to raise enough funds to bring him back home.

Those supporters were, at one time, legion: few men have had so many friends to lose, and few have done so as efficiently. An uncompromising radical, Trotter refused to budge in his beliefs, and that rigidity eventually alienated nearly everyone in his life, straining his relationships and draining his finances. He fought not only white enemies but also would-be black allies, including Booker T. Washington and W. E. B. Du Bois. He never ran for political office, but he was forever primarying the world from the left: the archive of the newspaper that he ran testifies to his willingness to attack anyone who did not share his exact vision of how to achieve racial justice.

Yet those same pages show just how clear-eyed that vision was. Trotter called for an anti-lynching bill and for federal enforcement of the Thirteenth, Fourteenth, and Fifteenth Amendments—which, for years, were largely theoretical propositions—and he insisted that protest and civil disobedience were the only effective remedies for racial discrimination. His legacy presents a challenge to those who seek change today: is compromise a necessary evil of any social movement, or is it the original sin of collective action?

A descendant of the Hemings family at Monticello, William Monroe Trotter was born on April 7, 1872, near Chillicothe, Ohio, just south of Columbus. His mother was the great-granddaughter of Sally Hemings’s sister, born free into a mixed-race family only one generation removed from slavery; his father was the child of an enslaved black woman and her white owner. Trotter’s parents were married in Ohio, after his father returned from fighting in the Civil War with the Massachusetts 55th; eventually, the family moved to Boston, where they raised their son and two daughters.

Black Bostonians, a quarter of the city’s population today, were a small minority when the Trotters arrived. Trotter’s father became the first black employee of the United States Postal Service, but, after being passed over for promotions because of his race, he resigned. Around the same time, he split with the Republican Party and joined the emerging negrowump movement, started by the pioneering black journalist T. Thomas Fortune and apparently named by analogy to the mugwumps—Republicans who refused to back their party’s nominee in the Presidential election of 1884. The negrowumps were angry that the party of Lincoln was not enforcing Reconstruction in the South, and the elder Trotter was rewarded for his political independence with an appointment in the Democrat Grover Cleveland’s Administration. As “recorder of deeds,” he was the highest-paid federal employee in the nation’s capital, earning forty thousand dollars in just two years. He invested much of it in real estate, before dying in 1892, of tuberculosis, at the age of fifty.

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Shopping Cartoon by Ellie Black

The younger Trotter inherited his father’s intellect and politics, along with, eventually, his wealth. After graduating as valedictorian and class president from Hyde Park High School, he enrolled at Harvard, where he became the first black member of Phi Beta Kappa. During college, Trotter was known for getting around on a bicycle before they were common. He also led the college’s abstinence club, hosted weekend Bible studies, and helped to push for an anti-discrimination law after a white barber in Cambridge refused to cut the hair of Harvard’s varsity football captain, a black All-American center and first-year law student. When the law faculty discouraged the student from filing a lawsuit against the barber, it became clear to Trotter and his friends that not even the Talented Tenth would be spared the humiliations of segregation or the faithlessness of ostensible white allies.

After graduating—with a bachelor’s degree, in 1895, and then a master’s, the following year—Trotter, who had toyed with the idea of becoming a minister, rejected a teaching job at a black school and spent a year applying for and not getting the banking and corporate jobs that he wanted. Meanwhile, his white peers, some of whom had weaker transcripts and thinner résumés than he did, were given opportunities more lucrative than the ones he was denied. He considered moving to Europe, where he felt he “would be recognized as a man,” but eventually found the kind of job he wanted with one of Boston’s most established real-estate firms. Between his salary and his commissions, he prospered, and soon broke away to open his own mortgage business. In 1899, he married his childhood friend Geraldine Pindell and bought her a stately home in Dorchester, one of the oldest neighborhoods in the city. Then he did the most radical thing he could think of: he started a newspaper.