Ben Reitman was a colorful figure. After tramping through Asia and Europe and around America several times as a youth, he returned to his hometown of Chicago, where a job as a janitor in a laboratory led him into medical studies. He obtained a medical degree in 1904 and later did pioneering work in the treatment and prevention of venereal disease.

Despite his entry into the respectable world of medicine, Reitman continued to go on periodic tramps and to use his position to benefit hobos, prostitutes, and other outcasts. In 1907, he earned the title of "King of the Hobos" for organizing a Chicago branch of the Hobo College, which served as a center for education, political organizing, and social services for tramps and other migrants.

Goldman met Reitman in March 1908. When Goldman was unable to find a place in Chicago in which to deliver a series of lectures, Reitman offered her the use of his "Hobo Hall." The two were immediately attracted to each other, and their relationship quickly blossomed into the most passionate love affair of Goldman's life. For much of the next decade, Reitman acted as Goldman's manager, and his skills of arranging and publicizing meetings, renting halls and promoting and selling anarchist literature contributed to the success of her repeated cross-country lecture tours.

The affair with Reitman caused Goldman both intense pleasure and intense pain. Madly in love, she was also wildly jealous of Reitman's many affairs with other women. When the time came to write about Reitman in her autobiography, Goldman was unable to be completely candid about the relationship, so torn was she about the conflicting emotions he had caused her.