The inmates at San Quentin are often highly intelligent–and usually sociopathic. Due to its racial and gang related violence, the residents refer to California’s oldest prison as “The Arena.” But aided by 4,000 volunteers, many prisoners try to improve themselves by taking undergraduate college courses, produce their own newspaper, organizing theatre productions, and engage in other endeavors. One inmate, Curtis Carroll, has been diligently studying financial analysis, and has built a reputation in the big house for teaching his fellow inmates how to become stock pickers as “The Oracle.” 

Carroll has plenty of time to focus on his craft. For the last 19 years, he has been serving 54 years to life on a sentence for murdering a man in an Oakland robbery when he was 17 years old. But on Thursday nights he packs a classroom with inmates focused on gaining insight and strategy about how to legally make a killing on Wall Street, according to a report by the local CBS News affiliate.

San Quentin Prison is the oldest prison in California. Located north of San Francisco in the heart of one of the world’s richest communities, San Quentin features California’s only gas chamber. Because of “The Arena’s” bloody reputation for gang warfare, cell block names include; “Little Viet Nam”, “Death Alley”, “OK Corral”.

Illiterate and sentenced as an adult when he was as a teenager, Carroll taught himself to read. At first he just read the newspaper sports pages, but eventually he discovered that the business section offered tremendous insight about finance and money. Carroll claims that he was shocked that the average person was legally allowed to this amount of money.

With unlimited time on his hands, Carroll developed his own strategy and began to invest. According to an interview with the local CBS affiliate in San Francisco, Carroll’s two disciplines rules for investing are, “Don’t buy stuff I don’t understand, and make sure that my research is very thorough.”

Carroll has been investing for the last decade, but his “rep” has grown since he was transferred to San Quintin in 2012. Built for approximately 3,000 prisoners, San Quentin is under court order to shrink because of overcrowding the facility with 4,223 inmates. The close quarters is blamed for much of the violence.

When other prisoners saw Carroll working on financial analysis, they asked for ideas. The enterprising Carroll helped dozens of prisoners and non-inmates who volunteer at the prison into “clients.” Since it is illegal to operate a business in a federal penitentiary, Carroll does not publish his performance numbers. Carroll told MarketWatch: “I’ve made loads of money in the stock market, for a whole bunch of people.

Carroll teaches in prison slang, and his three courses on financial and strategy are full each week. His first discipline, he tells his students, is to diversify. He relates that street gangsters understand that concept and usually branch out from selling drugs to prostitution and armed robbery. One of his most “shocking” beliefs is that Republicans are right that high taxes hurt the economy.

Carroll teaches that patient investing usually beats quick profits, especially for prisoners that are subject to long sentences. He emphasizes patient investing works even for the little guy, and tells prisoners they can start with $200-$500 and let time be their friend.

Lacking access to computerized trading, Carroll and his clients conduct trading through prison phone calls and “snail mail” to family members. But Carroll says the best thing about being focused on teaching legitimate investing is that his lessons will help fellow inmates avoid hopelessness and crime when they leave The Arena.

Photo: Reuters/File

Chriss Street suggests that if you are interested in California business and politics, please click on “Twenty Years after OC Bankruptcy and $5 Billion in Pension Debt“