Dion ‘Crazy’ Diamond, the ‘jail guest’ who protested segregation through private sit-ins from age 15

During the 1960s, a black teenager took it upon himself to protest for equal rights for African Americans.

Dion Diamond is a civil rights activist, who started protesting segregation and holding private sit-ins right from the age of 15.

Born on July 2, 1941, Diamond who grew up in Petersburg, Va. in the 1950s said he grew tired of looking at the “whites only” signs. That’s when he began what he calls “his own private sit-ins” at lunch counters and running out the back door whenever the police came.

Crazy Diamond, as he was called, knew how it felt like growing up as a teenager in the segregated South, so he would go to stores and lunch counters and occupy spaces that were meant only for white Americans.

He demanded service as a customer or delivered informal speeches until the police department was called, at which point he would escape the establishment through its back door.

Despite his many runs from law enforcement, Diamond continued with his sit-ins. His activism got him arrested more than 30 times, all for civil rights-related run-ins with the police.

Diamond attended Howard University in Washington D.C. Later, he transferred to the University of Wisconsin to study sociology and proceeded to study education at Harvard.

He participated in a sit-in at a local five-and-dime store with a group of black and white university students, and they drew attention from people who didn’t want them to protest.

At a point, Dion Diamond was sitting at a “whites only” lunch counter in Arlington, Va., in 1960 when a crowd started gathering around him.

Reportedly, a white boy pointed his finger at Dion and said, “Get out; you know you are not wanted here”.  

“I could only hope that as he got older, some of his attitudes regarding equality and equal rights changed,” Diamond told StoryCorps in Washington, D.C. years later.

Apparently, Diamond’s family had no idea what he was up to until the newspapers started calling his house. “You know like a reporter calls home, ‘Do you know your son is in jail?’ and my parents became very proud of me, but they wished it would have been somebody else’s child,” Dion said. “I’ve done some crazy things, but you take chances when you’re young. I call it youthful exuberance.”

Diamond was one of 13 individuals, seven African Americans and six whites who were refused service at a People’s Drug Store in Arlington, Virginia, 1960.

He was often arrested that he described himself as a ‘guest’ at the jail. At the time of his last arrest in Baton Rouge, La., Diamond narrated that “the white guards told these inmates, ‘we got a troublemaker here, gang. If you give him a hard time, you may get time off for good behavior”.

However, some of the inmates already knew who Diamond was, and they issued a warning: Don’t mess with him. “That was my salvation,” Diamond recalled.

He was in the 2nd freedom ride after one of the first buses was burned in Anniston, Georgia.

He was in the Greyhound bus which arrived in Jackson shortly after the Trailways bus carrying another group of Freedom Riders. They were arrested as soon as the bus arrived in Jackson and were sent to the Mississippi State Prison at Parchman.

Diamond was actively involved in the successful Washington, DC area effort to break Jim Crow in the suburbs.

He went to the historically black Southern University to urge students to strike and several were expelled from the school for picketing in the town for integration. This action led to his famous arrest in East Baton Rouge, LA for “criminal anarchy”, that is, attempting to overthrow the government of Louisiana.

Diamond served as a Student Non-Violent Coordinating Committee field secretary in Mississippi and Louisiana from 1961-63 and was a member of the DC area Non-Violent Action Group that led the campaign in the suburbs.

“Any time I pick up a historical publication, I feel as if a period or a comma in that book is my contribution,” 78-year-old Diamond mentioned.

In a bid to inspire young people to use their voices and fight for racial equality, Diamond still engages in public speaking.

Students of 2016 Rhode Island Milken Educator Award recipient and 2018 Lowell Milken Center Fellow Emily Caldarelli discovered Diamond as an unsung hero.