The Most Litigated Tax Issues

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Jason B. Freeman

Jason B. Freeman

Managing Member


Mr. Freeman is the founding member of Freeman Law, PLLC. He is a dual-credentialed attorney-CPA, author, law professor, and trial attorney.

Mr. Freeman has been named by Chambers & Partners as among the leading tax and litigation attorneys in the United States and to U.S. News and World Report’s Best Lawyers in America list. He is a former recipient of the American Bar Association’s “On the Rise – Top 40 Young Lawyers” in America award. Mr. Freeman was named the “Leading Tax Controversy Litigation Attorney of the Year” for the State of Texas for 2019 and 2020 by AI.

Mr. Freeman has been recognized multiple times by D Magazine, a D Magazine Partner service, as one of the Best Lawyers in Dallas, and as a Super Lawyer by Super Lawyers, a Thomson Reuters service. He has previously been recognized by Super Lawyers as a Top 100 Up-And-Coming Attorney in Texas.

Mr. Freeman currently serves as the chairman of the Texas Society of CPAs (TXCPA). He is a former chairman of the Dallas Society of CPAs (TXCPA-Dallas). Mr. Freeman also served multiple terms as the President of the North Texas chapter of the American Academy of Attorney-CPAs. He has been previously recognized as the Young CPA of the Year in the State of Texas (an award given to only one CPA in the state of Texas under 40).

The Taxpayer Advocate recently issued her annual report to Congress, identifying the ten tax issues that are most litigated in federal courts.  For purposes of this list, the term “litigated” refers to cases in which a court issued an opinion—so the list does not necessarily capture all of the most heavily disputed issues that are typically disposed of short of judicial resolution.  Nonetheless, the list provides insight into the world of tax controversy.

Those issues topping the most-litigated-tax-issues list include:

Among these issues, family status and relief from joint and several liability were not on the list last year, replacing the trust fund recovery penalty and the frivolous issues penalty, which both dropped off.

Notably, the Taxpayer Advocate noticed a marked increase (almost 14%) in the number of litigated cases involving issues on her Most Litigated Issues list, indicating that tax litigation is on the rise.

Freeman Law provides guidance and representation in tax litigation matters.  Freeman Law has substantial experience representing taxpayers in each of the categories topping the Taxpayer Advocate’s Most Litigated Tax Issues List.

For more tax resources, check out our other Insights, such as:


Tax Litigation Attorneys

Need assistance in managing the Tax Compliance process? With our unique substantive and procedural knowledge, we can provide a comprehensive approach to the tax dispute resolution process, often collaborating with clients’ existing tax professionals to formulate creative solutions to the most complex tax problems. Freeman Law offers value-driven legal services and provides practical solutions to complex tax issues. Schedule a consultation now or call (214) 984-3000 to discuss your tax concerns and questions.