Thomas D. Sykes Esq.

Managing Member
The Law Office of Thomas D. Sykes LLC

Thomas Sykes focuses his practice on tax compliance and controversies, including tax litigation in all forums. He has a blue-chip, nationwide federal tax practice in which he has advised or represented many of the nation's most successful, recognizable, and prestigious clients, including several very large state-owned institutions of higher education. He also handles tax controversies respecting state and local taxation, including those with the Illinois Department of Revenue and the City of Chicago. To his practice, Tom brings several key elements, including: 33 years of technical tax experience; almost 14 years of federal government service in Washington, D.C., where he represented the IRS in tax disputes nationally; 43 years of first-chair, in-court, trial and appellate experience; almost 5 years as a prosecutor in the Midwest.

Tom was at the forefront of the rapidly evolving litigation over FICA tax paid on stipends provided to medical residents – litigation that in March 2010 led the IRS to announce that medical-resident stipends are not subject to FICA for periods before April 1, 2005. This reversal of a long-time litigation position respecting an issue worth [blank] billions of dollars is one of the most notable reversals in IRS history. At the time of the IRS's capitulation, Tom was lead counsel in more FICA-related cases than any other attorney in the nation, and the only attorney identified by The Legal 500 (2010 ed.) for work in this field. In follow-on litigation, he represented many teaching hospitals seeking additional statutory interest upon refunds made in a $500 mm putative class action filed in the Court of Federal Claims. In addition to his in-court practice, Tom represents taxpayers before the IRS's Examination, Collection, Appeals, and Criminal Investigation Divisions, and before the IRS National Office.

After leaving an Assistant Chief post at the U.S. Department of Justice’s Tax Division in 1998, Thomas was a partner with a D.C. tax boutique, a partner with McDermott Will & Emery LLP, and a shareholder with Greenberg Traurig, LLP.

J.D., The Ohio State University College of Law (1979)
B.A., University of Wisconsin-Eau Claire (1976) magna cum laude

Bloomberg BNA Tax Management Portfolios:
524 T.M., Deductibility of Illegal Payments, Fines, and Penalties (co-author)

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