Robert H. (Bob) Gregory was born in Centralia, Illinois in December, 1952. He graduated from East Alton-Wood River High School in 1971 and then attended Milikin University in Decatur, Illinois, where he obtained a Bachelor of Arts degree, Summa Cum Laude, in 1975. Bob then attended the University of Illinois College of Law in Urbana-Champaign, receiving his Juris Doctorate (J.D.) degree in 1978.

Over the course of the next 26 years, Bob worked in a number of law firms, both large and small, and has tried cases in State and Federal Courts in sixteen different states.

In 1998, Bob and his wife, Roxanne (who is also his paralegal), opened their own law firm, dedicated to providing individualized service to their clients. Bob and Roxanne have three boys between them, all of whom are active outdoorsmen.

Bob is an avid fly fisherman and boating enthusiast and enjoys shooting skeet, trap and sporting clays.