Richard Ryan Bennett, J.D.

Advanced Planning & Family Office Practice Group
Chicago, Illinois

News & Information


Mr. Bennett is an Associate in the Advanced Planning & Family Office Practice Group at Handler Thayer. His practice is focused on tax compliance, planning and administration and estate planning, trust and estate administration, and wealth transfer planning. He has worked with a broad range of clients, including high net worth individuals seeking to implement carefully designed tax minimization strategies. He has experience handling complex trust and estate accounting, compliance returns for charitable trusts, and tax returns for trusts, estates, individuals, and partnerships. Mr. Bennett has also represented clients before the probate courts in Cook County and Lake County in connection with on-going estate administration matters.    

Mr. Bennett’s previous experience includes working as a judicial clerk for Judge Gerald E. Kubasiak of the Illinois Court of Claims.  In this capacity he routinely prepared bench briefs and drafted judicial opinions relating to civil procedure and jurisdictional matters. While studying for his Juris Doctor degree, Mr. Bennett was employed in the tax compliance department of a large technology company. He received his Juris Doctor degree with additional certificates in Taxation and Public Interest from Loyola University School of Law in Chicago, Illinois. He also earned joint Bachelor of Arts degrees with honors in both Finance and Politics from Lake Forest College in Lake Forest, Illinois.

In law school, Mr. Bennett was a recipient of the Dean’s List award every term and received a CALI award for the highest grade in his Corporate and Partnership Tax class and another CALI award in his Legal Writing class. He also received the prestigious William J. Kilbridge Award for Excellence in Federal Taxation and Clinical Studies. He was a published author and a staff editor of the Loyola Consumer Law Review, the only law review of its kind in the country.  Mr. Bennett is licensed to practice law in the State of Illinois and before the United States Tax Court.  He is a member of the Illinois State Bar Association and the Chicago Bar Association. 

Contact Information
Phone : (312) 641-2100


Chicago Office

191 North Wacker Drive, Ste. 2300

Chicago, Illinois 60606-1633

Naples Office

3050 North Horseshoe Drive, Ste. 154

Naples, Florida 34104-7911

Telephone: (312) 641-2100