Randy Picker graduated from the University of Chicago in 1980 cum laude with a BA in economics and was elected to Phi Beta Kappa. He then spent two years in the Department of Economics, where he was a Friedman Fellow, completing his doctoral course work and exams. He received a master's degree in 1982. Thereafter, he attended the Law School and graduated in 1985 cum laude. He is a member of the Order of the Coif. While at the Law School, Picker was an Associate Editor of the Law Review. After graduation, Picker clerked for Judge Richard A. Posner of the US Court of Appeals for the Seventh Circuit. He then spent three years with Sidley & Austin LLP in Chicago, where he worked in the areas of debt restructuring and corporate reorganizations in bankruptcy.
Picker is currently working on a book on the role of law in shaping competition in computers and computer platforms from roughly 1915 until today. The book relates to his Coursera online class Internet Giants: The Law and Economics of Media Platforms.
He has played a number of administrative roles at the University of Chicago, including serving as faculty spokesman in 2016-17. He also chaired a University committee charged with reviewing and making recommendations about procedures for student disciplinary matters involving disruptive conduct including interference with freedom of inquiry or debate.