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Attorney Jonathan Decatorsmith

chicago tax attorney Jonathan Decatorsmith AVVO

Managing Attorney

chicago tax attorney Jonathan Decatorsmith AVVO

Chicago tax attorney Jonathan Decatorsmith has been practicing tax law for more than 30 years. Prior to joining the Law Offices of Chicago-Kent, Decatorsmith was a senior trial attorney and internal instructor with the Internal Revenue Service for 11 years. He has tried more than 50 cases before the United States Tax Court, U.S. District Court, 7th Circuit Court of Appeals, and Illinois Independent Tax Tribunal. He previously served as an adjunct professor at DePaul University in Chicago and the University of Minnesota.

In 2000, Professor Decatorsmith joined the IIT Chicago-Kent College of Law as a full-time clinical professor, and took over the Low Income Taxpayer Clinic. Over the years, the clinic grew from formally representing 42 indigent clients (in 2000) to more than 350 individual taxpayers annually, gaining a reputation as one of the preeminent tax clinics in the country. Utilizing the services of student interns, whom Professor Decatorsmith trained in the practice of aggressive and ethical tax controversy representation, the clinic became particularly recognized for its numerous appearances on behalf of lower income petitioners in the United States Tax Court.

In January of 2012, Decatorsmith transformed the tax clinic into its present, fee-based model. It was later re-named The Tax Practice, to distinguish the firm from its teaching arm, The Tax Clinic, and services were expanded to include tax return preparation, tax and business transaction counseling, not-for-profit organization formation and compliance, and criminal tax representation. Recently, the practice modified its scope of services to focus on IRS and state audits, appeals, and litigation, along with nonprofit organization work and selected transactional advice and commercial litigation.

Besides managing The Tax Practice and supervising the Tax Clinic, Decatorsmith teaches courses on federal tax practice and procedure, international business transactions, estates and trusts, tax fraud, and other topics. He is a sought-after speaker, and for many years presented annually at the IRS Low Income Taxpayer Clinic conference in Washington, D.C. on a variety of topics, including IRS Appeals, Collection Strategies, and Tax Court Practice. He has also lectured on Tax Debt Relief Strategies to the Chinatown Merchants Association and various community organizations in the Chicago area. Decatorsmith recently authored Chapter 24 (Taxation) of the Illinois Jurisprudence volume on Immigration.

In September of 2021, Decatorsmith was appointed Director of Clinical Education, overseeing all of Chicago-Kent’s clinical education programs.

As a strong advocate for taxpayers rights, Decatorsmith is frequently cast as the lone defender of the powerless against the Internal Revenue Service and Illinois Department of Revenue bureaucracies. The Tax Practice at IIT Chicago-Kent College of Law, under his leadership, has become particularly adept at negotiating on behalf of individuals and businesses creative and successful resolutions to significant federal and state problems.



  • University of Colorado School of Law at Boulder, J.D., 1986
  • University of Illinois, B.A., 1983

Bar Admissions

  • Illinois State Bar, 1986
  • U.S. Tax Court Bar, 1987
  • Various tribal and federal courts

Honors and Awards

  • Lead Instructor for the IRS National Trial Skills School, 1995
  • IRS Midwest Attorney of the Year, 1994

Published Works

  • Illinois Jurisprudence, Immigration, Chp. 24 Taxation (October 2014)

Notable Tax Court Cases

Employment Experience

IIT Chicago-Kent College of Law, Chicago, IL (2000-Present)

  • Managing Attorney, The Tax Practice of IIT Chicago Kent College of Law
  • Director of Clinical Education
  • Clinical Professor of Law, IIT Chicago Kent College of Law Tax Clinic
  • Teaches Federal Tax Procedures, Estates and Trusts, Tax Fraud Seminar, Introduction to American Legal Systems, Business Organizations and International Business Transactions
  • Teaches overseas in China, Thailand, Armenia, Istanbul, Athens, and Georgia in International LL.M Program

BlueDog, Olsen and Small, Minneapolis, MN (1999-2000)

  • Senior Associate

Chief Counsel Office of the Internal Revenue Service, Chicago, IL (1987-1999)

  • Senior Trial Attorney and Internal Instructor

University of Minnesota, Minneapolis, MN (1996-1999)

  • Adjunct Professor

DePaul University, Chicago, IL (1990-1995)

  • Adjunct Professor
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