Jenny L. Johnson

  • T 312.578.6523

Jenny Louise Johnson, a partner in Holland & Knight’s Chicago office, leads the Tax Controversy and Litigation Team.

Ms. Johnson handles complex tax disputes of significant value for clients ranging from individuals to multinational corporations. She represents taxpayers in all stages of criminal and civil tax proceedings, including voluntary disclosures, sensitive audits and examinations, IRS appeals, summons enforcement, search warrants, grand jury subpoenas, negotiated resolutions with the IRS and the Department of Justice, trials in federal district court and the U.S. Tax Court, sentencings and appellate litigation. She has successfully resolved disputes involving income taxes, estate and gift taxes, excise taxes, federal and state tax credits, employment taxes, employee plan matters and tax exempt bonds.

As a skilled trial lawyer with a sophisticated understanding of tax issues and extensive experience in each of the many forums where tax disputes get resolved, Ms. Johnson offers her clients creative and practical solutions that are customized to achieve the goals that are most important to each client. By bringing the perspective of a trial lawyer to the development of a case from the very beginning, she is often able to avoid the expense and uncertainty of protracted litigation and achieve a favorable settlement. When that is not possible, she is a powerful and seasoned advocate in the courtroom.

Ms. Johnson also routinely provides behind-the-scenes strategic counseling to clients and their other advisors on potential or existing tax-related disputes. For example, Ms. Johnson frequently works with high net worth individuals, families and their other advisors to identify potential audit risks and navigate enterprise examinations pursued by the IRS Global High Wealth Industry Group.

Ms. Johnson’s recent experience includes: 

  • serving as lead tax litigation counsel for a $3 billion estate with respect to an alleged $150 million estate and gift tax deficiency involving transfer of interests in a professional sports team
  • obtaining summary judgment for the taxpayer, defeating the government’s attempt to recover what it claimed was an erroneous tax refund, with the U.S. District Court repeatedly citing her arguments on complex aspects of the TEFRA regulations
  • trying three cases in the United States Tax Court involving alleged transferee liability in “Midco” intermediary tax shelter cases, including one victory and two cases currently awaiting final decision
  • successfully resolving a Global High Wealth Industry Group audit involving tax treatment of millions of dollars of state low income housing tax credits and various other complex issues at the individual and entity levels
  • winning a $5 million U.S. Tax Court trial by proving that the taxpayer materially participated in a business through activities that included entertaining potential investors
  • defending multiple clients in the bar and restaurant sector in criminal tax investigations and prosecutions, as well as the civil aftermath
  • negotiating a favorable resolution of an IRS audit involving executive compensation 
  • representing multiple taxpayers in various claims for refund from IRS, including claims for penalty abatement and refunds relating to gifts and inheritances
  • supervising a team representing hundreds of taxpayers who are voluntarily disclosing to the IRS funds held in offshore bank accounts and related income tax liabilities
  • representing multiple plan sponsors who faced an IRS threat of disqualification of their qualified plans
  • convincing the IRS to abate over $1 million in penalties and interest resulting from misapplication of seized funds

Ms. Johnson is an adjunct professor on the tax faculty at Northwestern University School of Law, currently teaching Investigation, Prosecution and Defense of Tax Crimes, and a visiting lecturer at the University of Chicago School of Law. She is also a frequent speaker and faculty member at both national and international professional conferences, and is in the upper echelon of nationally recognized tax litigators.

Ms. Johnson launched a new pro bono initiative in Chicago, representing low income taxpayers in front of the U.S. Tax Court. Partnering with the Center for Economic Progress, Ms. Johnson and her team developed a program to train attorneys and law students to represent low income taxpayers, and then appear in court to assist taxpayers who arrive for their required hearing without legal assistance. She also represents children in juvenile delinquency proceedings, immigrants seeking asylum and those who have been wrongly convicted.

Honors & Awards

  • Illinois Super Lawyers magazine, 2016
  • Rising Star, Illinois Super Lawyers magazine, 2013-2014
  • Chicago's Rising Stars: 40 Under 40, The National Law Journal, 2013


  • American Bar Association, Section of Taxation, Civil and Criminal Tax Penalties Committee, Vice Chair
  • American Bar Association, Real Property, Trusts and Estates Law Section, Income and Transfer Tax Planning Group, Tax Litigation and Controversy Committee, Chair
  • American Bar Association, Criminal Justice Section, White Collar Crime Committee
  • Harvard Law Society of Illinois, Board of Directors
  • Chicago Inn of Court