Reitman was a flamboyant, eccentric character. Goldman conveys a sense of this when she describes first meeting Reitman in her autobiography, Living My Life:
He arrived in the afternoon, an exotic, picturesque figure with a large black cowboy hat, flowing silk tie, and huge cane. "So this is the little lady, Emma Goldman," he greeted me; "I have always wanted to know you." His voice was deep, soft, and ingratiating. I replied that I also wanted to meet the curiosity who believed enough in free speech to help Emma Goldman. My visitor was a tall man with a finely shaped head, covered with a mass of black curly hair, which evidently had not been washed for some time. His eyes were brown, large, and dreamy. His lips, disclosing beautiful teeth when he smiled, were full and passionate. He looked a handsome brute. His hands, narrow and white, exerted a peculiar fascination. His finger-nails, like his hair, seemed to be on strike against soap and brush. I could not take my eyes off his hands. A strange charm seemed to emanate from them, caressing and stirring...
Reitman was born in St. Paul, Minnesota, to poor Russian Jewish immigrants in 1879, but grew up in Chicago. At the age of ten, he became a hobo, but returned to Chicago and worked in the Polyclinic Laboratory as a "laboratory boy". In 1900, he entered the College of Physicians and Surgeons in Chicago, completing his medical studies in 1904. During this time he was briefly married; he and his wife had a daughter together.
Reitman met Emma Goldman in 1908, and the two began a passionate love affair, which Goldman described as the "Great Grand Passion" of her life. The two traveled together for almost eight years, working for the cause of birth control, free speech, worker's rights, and anarchism.
During this time, the couple became involved in the San Diego free speech fight in 1912–13. Reitman was kidnapped by a mob, severely beaten, tarred and feathered, branded with "I.W.W.," and his rectum and testicles were abused. Several years later, the couple were arrested in 1916 under the Comstock laws for advocating birth control, and Reitman served six months in prison.
Both believed in free love, but Reitman's practice incited feelings of jealousy in Goldman. He remarried when one of his lovers became pregnant; their son was born while he was in prison. Goldman and Reitman ended their relationship in 1917, after Reitman was released from prison.
Reitman returned to Chicago, ultimately working with the City of Chicago, establishing the Chicago Society for the Prevention of Venereal Disease in the 1930s. His second wife died in 1930, and Reitman married a third time, to Rose Siegal. Reitman later became seriously involved with Medina Oliver, and the couple had four daughters — Mecca, Medina, Victoria, and Olive.
- The Second Oldest Profession - A Study of the Prostitute's "Business Manager" (1931) A sociological study of pimps.
- Sister of the Road: The Autobiography of Boxcar Bertha (1937) (fiction)
- No Regrets: Dr. Ben Reitman and the Women Who Loved Him : A Biographical Memoir by Mecca Reitman Carpenter. (biographical memoir by Reitman's daughter)
- Frank O. Beck, Hobohemia: Emma Goldman, Lucy Parsons, Ben Reitman & Other Agitators & Outsiders In 1920s/30s Chicago (Charles H. Kerr Press, 2000, ISBN 978-0-88286-251-4 (description)
- Roger Bruns, The Damndest Radical: The Life and World of Ben Reitman, Chicago's Celebrated Social Reformer, Hobo King, and Whorehouse Physician (University of Illinois, 2001)
- Mecca Reitman Carpenter, No Regrets: Dr. Ben Reitman and the Women Who Loved Him (SouthSide Press, 1996) (description at SouthSide Press)
- Emma Goldman, Living My Life (1931)
- University of Illinois at Chicago, University Library, "Ben Reitman Biographical Sketch", Reitman papers.
- Alice Wexler, Emma Goldman: An Intimate Life. New York: Pantheon Books, 1984. ISBN 0-394-52975-8. Republished as Emma Goldman in America. Boston: Beacon Press, 1984. ISBN 0-8070-7003-3.
- Tim Cresswell, The Tramp in America. London: Reaktion Books, 2001. ISBN 1-86189-069-9.
- Emma Goldman, Living My Life, Volume 1.
- Reitman profile, UIC.
- John A. Farrell, Clarence Darrow: Attorney for the Damned, (Doubleday 2011), p. 243. ISBN 978-0-385-52258-8
- Wexler, Intimate, pp. 211–215.
- Wexler, Intimate, pp. 140–147.
- "Browse by City: Forest Park". Findagrave.com. Retrieved 2008-05-05.
- A sociological study of pimps by Dr. Ben Reitman, founder of the Chicago hobo college Goodreads
- Boxcar Bertha: Tales spun from the hobo world The Portland Alliance, Ruth Kovacs, November 2002 issue
- "Despite decades of scholarship claiming otherwise, Boxcar Bertha is not a real woman but an imagined representation of unconventional female life in the early twentieth century. In her unpublished dissertation, Martha Reis carefully documents the lives of the women who inspired Bertha’s character, including a female pickpocket, anarchist, and ex-patriot poet." Venturing More Than Others Have Dared: Representations of Class Mobility, Gender, and Alternative Communities in American Literature, 1840-1940; dissertation, Heather Joy Thompson-Gillis, MA, The Ohio State University 2012
- Hidden histories, Ben Reitman and the "outcast" women behind Sister of the Road : the autobiography of Box-Car Bertha Martha Lynn Reis, dissertation, Ph. D. University of Minnesota 2000
- The More Things Stay the Same [Documentary on Ben Reitman]
- PBS American Experience
- Emma Goldman Ephéméride Anarchiste
- Anarchist Encyclopedia cited
- "Ben Reitman". Find a Grave. Retrieved August 10, 2010.
- Ben Lewis Reitman Papers, University of Illinois at Chicago (letters and papers from 1907 to 1989)