In 1996, Ross was sentenced to life imprisonment under the three-strikes law after being convicted for purchasing more than 100 kilograms of cocaine from a federal agent in a sting operation. Later that year, a series of articles by journalist Gary Webb in the "San Jose Mercury News" revealed a connection between one of Ross's cocaine sources, Danilo Blandón, and the CIA as part of the Iran–Contra affair. Having learned to read at the age of 28, during his first stint in prison, Ross spent much of his time behind bars studying the law. He eventually discovered a legal loophole that would lead to his release. Ross's case was brought to a federal court of appeals which found that the three-strikes law had been erroneously applied and reduced his sentence to 20 years. He was released from Federal Correctional Institution, Texarkana on September 29, 2009.