Stuart attended Northern Illinois University where he majored in political science. He received a Bachelors of Arts in 1984 and went on to obtain his Law degree from John Marshall University and was subsequently accepted into the Illinois Bar Association in 1987.

Stuart worked for the State of Illinois, Department of Children and Family Services for a little over one year before joining the private sector. After getting experience with one of the biggest bankruptcy firms in Chicago, Stuart opened The Law Offices of Stuart B. Handelman in 1992. Stuart is a member of the Chicago Bar Association, Will County Bar Association and the American Bankruptcy Institute.