Lindsay majored in history and literature, graduating from Tulane University in 1984. He earned his law degree from St. Louis University in 1988. Since then, Lindsay also earned MAs in literature and history from DePaul and Loyola-Chicago. He practiced law in the office of the Cook County Public Defender from 1990 to 2018 when he was elected to the bench as a Circuit Judge of Cook County. Lindsay has taught history and law courses at DePaul and Columbia College since 1998. He has served on the boards of CityLit Theater and the Cliff Dwellers Arts club, where he also initiated and has hosted their live jazz program for over five years. Lindsay also founded and heads the Friends of Bezazian Branch library support group in the Uptown community of Chicago where he has resided for over 30 years.