Judge Cunningham brings decades of experience as a defense attorney, a prosecutor and a judge to this position. Prior to becoming the Public Defender, he served on the Cook County Circuit Court from 1986, to 2009, where he's presided over thousands of bench trials and hundreds of jury trials, in both criminal and civil cases. His last assignment was to the Law Division, where he presided over civil jury trials in areas that included personal injury/wrongful death, motor vehicle injury, medical malpractice, product liability, commercial litigation and breach of contract.

Judge Cunningham graduated from Fisk University in 1969 with a Bachelor of Science • Degree, and from Northwestern University School of Law in 1972. He served as legal advisor to the State Superintendent of Public Instruction from 1972-1973, when he left to joined the Cook County State's Attorney's Office as a felony trial assistant and then as Chief of the Vertical Prosecutions Unit. In 1976, Judge Cunningham joined the Criminal Defense Consortium of Cook County as a Supervising Attorney working out of the Lawndale office of the Consortium. The Consortium consisted of a network of five community-based law offices providing criminal defense services for indigent residents of the community accused in felony, misdemeanor and juvenile cases.

After a period in private practice as a litigator in criminal and civil defense, Judge Cunningham rejoined the Office of the Cook County State's Attorney, where he supervised 40 Assistant States Attorneys responsible for prosecuting all criminal misdemeanor and quasi-criminal cases in1  the City of Chicago, as well as advising the office on legislative issues. He left this position to join the bench in 1986.

Judge Cunningham was appointed by the Chief Judge to mentor newly appointed and elected judges, and is certified in Comprehensive mediation in the State of Illinois. His professional affiliations include membership in the American Bar Association, the National Bar Association, the Cook County Bar Association and the Chicago Bar Association, the Illinois Public Defender Association and the National Legal Aid and Defender Association. He has been an adjunct professor in the Political Science Department at the University of Illinois at Chicago, and was also an adjunct professor at the DePaul University School of Law and the John Marshall School of Law.