Former San Quentin prison guard and undercover detective Darren Monahan recently shared insights from his early days working at the infamous California prison. Growing up near the Bay Area, Monahan initially considered becoming a police officer but was recruited unexpectedly at a local fair by San Quentin’s hiring team in 1985. Intrigued by the pay and opportunity, he applied and eventually graduated from the Corrections Academy.Starting as a 21-year-old in what was then considered one of the toughest prisons in America, Monahan’s first assignment was working the kitchen alone before dawn. He quickly learned the intricate and dangerous realities of prison life, including handling inmates of varying security levels and understanding prison culture—where even sugar was a coveted commodity. Monahan recounted moments of tension, including being threatened when he called a Black inmate “boy,” highlighting the volatile environment guards faced daily. His experience sheds light on the challenges and complexities of working behind San Quentin’s walls during its notorious era.