Glenn Bailey has served 52 years inside the California carceral system. The last 42 were part of a life sentence for a double homicide he readily admits he committed.
When he was arrested, authorities arrested another man as his accomplice. A man that Bailey had never met. The officer who arrested Bailey ended up spending time in a cell at San Quentin, where Bailey who went from “High Society Red” to “Triple OG Bailey” was also incarcerated. This is a story in which it’s difficult to tell the good guy from the bad guy.
Bailey is a Lifer at Large, part of a growing demographic of elderly men who have served more than a half-century behind bars, inside a system some compare to chattel slavery. He saw the birth of 3 strikes from the lens of 25 to Life. He saw the prisons swell with young Black men who became casualties of the war on drugs. When Bailey went to prison, California only had two formal prisons. By the time he was paroled in November 2012, private prisons for profit were a thing.
When he returned home, one of his missions was to save young men from following in his footsteps. Another mission for Bailey is the reframing of his relationship with the world. High Society Red went to prison. Triple OG Glenn Bailey came home. The story of Bailey’s resilience starts earlier. Before High Society Red, before prison, and before Oakland, where he would kill two people before he figured out how to live.
Like a lot of Californians, Bailey is a transplant. He started out in New Orleans and migrated to Oakland with his mother when she left his father–a White man who owned the plantation-like spread across from where his mother and he spent his early years. Bailey shares a story about his father giving him a sack to pick cotton on his land.
The younger Bailey took pride in filling the sack and remembers his father taking it away and burning it with the admonishment that Glenn, as his son, was too good to pick cotton. His “high yellow” tone and piercing blue eyes made him a target in West Oakland where his mother joined a sister who had left the South before her. Perhaps the thought that he was due something in life came from the lesson his father taught him.
The story of his youth in West Oakland is an American tale. Black and living in a redlined city with a dynamic population, with freedom to buoy the spirit of “yes we can.” As Bailey described it, he hardly knew a Black man who didn’t have a hand in something. It seemed his path was paved and he slid down it with gusto. He, by his own admission learned to be a man, a father, and a friend, in prison.
The status of “Triple OG” is iconic and Bailey is a legend whose story blurs lines between those imprisoned and those who hold the keys. When you do as much time as he has, you grow up with the staff. His stories of life behind bars are even more colorful than his stories of being the smooth and lethal hustler known as High Society Red.
He is currently battling cancer. For the fifth time.
Glenn Bailey is the focus on ‘Lifer,’ a stage performance written by Ayodele Nzingha.