Thomas D. Sykes Esq.


A Partner with Gould Ratner LLP in Chicago, 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 advises or represents 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: 31 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; 35 years of first-chair, in-court, trial and appellate experience; almost 5 years as a prosecutor in the Midwest.
     This "360-degree" combination of elements enhances Tom's ability to realistically assess the legal hazards faced by a taxpayer involved in a tax dispute, to plot, pursue and implement a strategy for settlement that comprehends the inner workings of both the IRS and the Department of Justice, and to resolve efficiently administrative proceedings and any subsequent litigation that becomes necessary. Tom's representation does not require him to be yoked to a general litigator, a less efficient and more expensive "two-headed" approach used by many law firms in handling tax litigation. Moreover, his first-chair appellate experience makes it unnecessary to bring in a new lawyer to handle any appeal that is taken. Tom is one of only a handful of tax lawyers in private practice nationally to have first-chaired more than 20 jury trials and at least ten appeals.
     Since 2005, Tom has been 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 many 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. He currently represents many teaching hospitals that seek additional statutory interest; and many state-owned teaching hospitals seeking refunds based upon the state's Section 218 Agreement – an issue not addressed in the Mayo Foundation decision.
     With his experience at the Department of Justice in Washington and as a long-time partner in private law practice, Tom may have handled a greater number of tax-refund suits in the federal trial courts than any attorney now active in private practice in the United States. 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.
      Prior to joining Gould Ratner, Thomas was a Shareholder with Greenberg Traurig, LLP. Before being a shareholder with Greenberg Traurig LLP, Thomas was a partner with McDermott, Will & Emery 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)