The nickname "Freeway" came from Ross's ownership of several properties along the Los Angeles-area Harbor Freeway as well as the existence of a freeway near his childhood home. During the height of his drug dealing, Ross claims to have sold "$2 million in one day." According to the Oakland Tribune, "In the course of his rise, prosecutors estimate that Ross exported several tons of cocaine to New York, Ohio, Pennsylvania and elsewhere, and made more than $600 million in the process. Adjusting for inflation using the Consumer Price Index, that is more than a billion dollars.

In 1996, Ross was sentenced to life imprisonment after being convicted of trying to purchase more than 100 kilograms of cocaine from a federal agent. Ross became the subject of controversy later that year when a series of articles by journalist Gary Webb in the San Jose Mercury News brought to light a connection between one of Ross's cocaine sources, Danilo Blandon, and the CIA as part of the Iran-Contra scandal. The decision in Ross's case was brought to a federal court of appeals where his sentence was reduced to 20 years. His sentence was then reduced further due to being a model prisoner, and he was moved to a halfway house in California in March 2009. Ross is now founder of non profit Freeway Literacy Foundation, and working on his biopic feature film.