Editor Ruby is here this week, bringing you the tidbits we learned this Black History Month that we couldn’t fit into our questions. We’ve got two very cool people from history here, brought to you in chronological order.

First up, we have Robert Smalls. Born into slavery in 1839, Smalls was sent to work at the docks in Charleston at the age of 12. His enslaver (and possibly his biological father, uncle, or grandfather) Henry McKee took $15 of the $16 he earned every week, “letting” Smalls keep one dollar per week. After getting married at age 17 and having several children, Smalls attempted to purchase his and his family’s freedom with the $100 he had saved up. Their enslavers counter-offered $800, or over $24,000 in today’s money.

Seeing the situation was impossible, Smalls used his familiarity with Charleston’s harbor and his passing visual resemblance to Confederate Captain Relyea to stage a daring and successful escape. At age 22, in 1862, Smalls commandeered a Confederate ship, the C.S.S. Planter, when its captain and his white officers disembarked for the evening, leaving the enslaved crew led by Smalls alone for the night. Smalls wore Relyea’s clothing and mimicked his body language to pass through a Confederate checkpoint under the cover of darkness. Without raising the alarm, he and the crew sailed it straight into the Union blockade of Charleston, flying a sheet his wife Hannah brought along as a white flag. (Go read the excerpts from eyewitness accounts; they are thrilling.)

Smalls continued a heroic military career to free more people from slavery. His example convinced President Lincoln to allow Black soldiers to fight for the Union, and he personally recruited over 5,000 people to the effort. He continued to serve on what then became the U.S.S. Planter, taking over for its white captain after he abandoned his post by hiding in the coal room during a particularly violent fight. After the war, Smalls used the money he was awarded for the requisition of the Planter, $1,500, to buy the home his former enslaver had surrendered to the U.S. government due to not paying taxes. McKee attempted to sue him, but Smalls won the case, establishing an important precedent for freed people and their property rights.

Smalls went into politics and was elected to the South Carolina Legislature in 1868 and to the U.S. House of Representatives in 1874. As a South Carolina senator, he wrote the bill that established the first public and compulsory public school system in the U.S. While his efforts to prevent the end of Reconstruction were largely thwarted, he ended his career as the longest-serving Black member of the House until the mid-20th century. He died at the age of 75, in 1915.

Born in 1907, just eight years before Smalls’ death, we have Gladys Bentley. Bentley was born in Philadelphia and described herself as always having been more comfortable in boys clothes. Conflict with her parents over her gender nonconformity led her to run away to New York at age 16. She broke into show business in the Prohibition-era speakeasies of Harlem, wearing some incredible outfits.

Speaking about queer people in the past is always tricky — maybe if she were born today, Bentley would identify as a man, but in the parlance of the time, she understood herself to be a lesbian and a “bulldagger” (a term that took on pejorative connotations after the period she used it). The sources I can find refer to Bentley with she/her pronouns and describe her stage persona as something like a drag king. She performed vulgar parodies of popular songs with a backup chorus of drag queens in popular Harlem social clubs in the ’20s. You can hear some of her recorded music (reportedly toned down and stripped of the lesbianism of her stage shows) to get a sense of her style.

Bentley was riding high in the ’20s: she either owned an expensive penthouse on Park Avenue or lived with one of her girlfriends there. She flirted with women in her audiences and got married to her white girlfriend in 1928 in Atlantic City. Langston Hughes wrote about her: “Miss Bentley was an amazing exhibition of musical energy – a large, dark, masculine lady, whose feet pounded the floor while her fingers pounded the keyboard – a perfect piece of African sculpture, animated by her own rhythm.” The venue she first performed at was called Harry Hansberry's Clam House (already great) and was later renamed Barbara's Exclusive Club after her stage name, Barbara Minton. She toured the country and was beloved by celebrities and artists.

The end of Prohibition hit Harlem’s speakeasies hard, and she moved with her mother to Southern California. Increasing policing of the gender binary through the ’30s and ’40s led to harassment in her personal life and marginalization of her act. During the McCarthy era, she described herself as “cured” of homosexuality in an essay called “I Am a Woman Again,” in which she claimed to be married to one man (who denied it) and later married a much younger man. Again, we can’t make too detailed of claims about the identities of people in the past, but the direct threat to her, and all other LGBTQ+ people’s, livelihood and freedom in the ’50s can’t be taken out of her decision to start wearing dresses and claim heterosexuality. Unfortunately, she passed away at the age of 52 from a sudden flu. You can see her shortly before her death on Groucho Marx’s game show “You Bet Your Life.”