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From 1987 to 1990, he was a staff attorney at Westside Legal Services, in Santa Monica, California where he was the lead trial lawyer representing lower income families and individuals who could not afford a lawyer. In 1990, DeSimone founded the cutting edge civil rights law firm Schonbrun & DeSimone. Later known as Schonbrun DeSimone Seplow Harris & Hoffman, the firm established a reputation as one of the most prestigious civil and employment rights law firms in the State of California and in the entire country.
After twenty-five years as a partner, Jim decided to carve out his own path by establishing V. James DeSimone Law, a California law firm dedicated to representing individuals in civil rights cases, with an emphasis on employment discrimination and harassment, employment wage and hour class action cases, police misconduct and brutality cases, including wrongful death, excessive force, and false arrest cases, and personal injury cases.