Harold “Hal” Madison Jennings, a distinguished criminal defense attorney and longtime resident of Bloomington, Illinois, passed away peacefully on May 5, 2025, in Normal, Illinois, just days shy of his 85th birthday.
Born on May 13, 1940, in Cincinnati, Ohio, Hal dedicated over five decades to the practice of law in and around McLean County. He began his legal career in 1964 and served as a felony prosecutor in St. Clair County from 1965-1968. Hal then moved to Bloomington, where he served as McLean County’s first assistant state’s attorney before transitioning into private practice in late 1970. There, he built a reputation as one of central Illinois’ most respected and formidable criminal defense attorneys, trying more than 800 cases over his career—many of them high-profile trials that left an indelible mark on the region’s legal landscape.
Hal was known for his sharp legal mind, commitment to due process, and fierce advocacy for his clients. His courtroom presence and mentorship left a lasting impact on many attorneys and earned him widespread respect among colleagues, judges, and juries alike.
Hal earned both his B.A. (1962) and J.D. (1964) with distinction from the University of Illinois. Beyond his legal practice, he contributed to legal education as an instructor at Illinois State University, Sangamon State University, and Illinois Central College. He was named Bloomington city attorney in 1972 and served in that part-time capacity until June 1974. Hal also authored a chapter: Representing the Criminal Defendant from File to Trial in the Illinois Institute for Continuing Legal Education’s 1993 publication, Law at a Glance: Legal Assistant’s Guide to the Law. He was a decades-long member of the Illinois Association of Criminal Defense Lawyers and served as a member of the McLean County Domestic Violence Task Force when it was founded in the early 90s.
In 2006, Hal retired to South Carolina, believing he had practiced enough law. After completing the first draft of a novel based on a civil case that had long occupied his thoughts, he realized that retirement did not suit him. With his wife's support, he returned to Bloomington in late 2009 and resumed his legal practice, quipping at the time, "I'm too old to learn anything new."
Hal was a man of few words but came alive in the courtroom. In his free time, he was a voracious reader and writer, loved to travel–collecting the “ugliest” hats he could find as souvenirs, and enjoyed fishing and tennis. Hal appreciated a good glass of brandy with friends and could often be found attempting to bribe his family for dessert. He was known for his dry wit and signature “ho hum.”
Hal was preceded in death by his parents, Leslie Jennings and Mildred (McConnell) Jennings; his brother, Leslie "Buster" Jennings Jr.; and his sister, Ann (Jennings) Shannon. He is survived by his beloved wife of 33 years, Cathy; his children, Patrick (Li) Jennings, Christopher (Jen) Jennings, Erin Jennings, and Nolan Harper; his grandchildren, Ellie and Rigby Harper; and many dear friends. Hal will be deeply missed by those who knew and loved him.
A celebration of life open house will be held Sunday, June 1, 2025, from 1 - 4 p.m. at Jim’s Steak House in Bloomington, with arrangements handled by Carmody-Flynn. In lieu of flowers, the family requests that donations be made to the Humane Society of Central Illinois, the Alzheimer’s Association, or the Innocence Project.