He graduated from Tufts University in 1962 and received his law degree from Columbia Law School in 1965. Following his graduation, Fine was a law clerk to Judge George Rosling of the United States District Court for the Eastern District of New York and worked for three years as an appellate attorney in the United States Justice Department Civil Division. After leaving the Justice Department, Fine relocated to Brown Deer, Wisconsin, and became a full-time writer, publishing a legal novel titled Mary Jane vs. Pennsylvania, a critique of the pharmaceutical industry, and several law journal articles.
