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Thomas D. Sykes
16625 Redmond Way Ste. M #151
Redmond, WA 98052
(847) 651-7881

In the nation’s industrial, legal, tax, and political power centers, Tom built a singular, premier, large-dollar, 360-degree tax-litigation, trial, and appellate resume. After getting his start in Wisconsin as a District Attorney and as a federal prosecutor, Tom began litigating civil tax cases in 1984 in DC for the U.S. Department of Justice’s Tax Division (DOJ). First chaired or directly supervised perhaps 250 tax cases in federal courts across the nation and in the Court of Federal Claims. Over his career, first chaired 15 cases in the federal courts of appeals and tried 25 jury trials; and handled $3bn to $4bn in tax cases overall. Seventeen years total with DOJ, including seven years of DC-based supervisory experience. Went into private practice in 1998, when he joined a DC tax boutique as a partner, litigating cases for large insurance companies. In 2002, joined as a partner the Chicago office of the nation’s largest law-firm tax practice, representing and assisting some of the nation’s largest corporations and nonprofits, and wealthiest individuals and families. Led the charge, nationwide, in the successful effort to recover about $2bn in FICA tax for the nation’s 360 teaching hospitals, notching pivotal wins in The University of Chicago Hospitals’ $38mm case in both the trial court and in the Seventh Circuit. Had more teaching-hospital cases pending in court than any other attorney in the nation when the IRS totally conceded for taxable periods before 2Q2005. First-chaired a case for Cemco, a Paul Daugerdas entity, in litigation in both federal district court and the Seventh Circuit that presented a novel partnership-audit procedural issue. Obtained full-concession of a $15mm bet-the-company, prohibited-transaction penalty case in Tennessee. In 2010 joined as a shareholder the law firm that is now one of the nation’s largest. Founded own law firm in January 2016 to pursue a $500mm federal-tax class action for about 300 teaching hospitals (concluded in 2019). Among other accolades (below), is a thirteen-time, peer-selected Illinois Super Lawyer in Tax (top 5%), including 2013-2021. Extensive experience with litigation finance. Followed spouse’s career to Seattle area in August 2019.

Law Offices of Thomas D. Sykes PLLC, Lake Forest, IL and Redmond, WA. Managing member. Nationwide federal tax-litigation practice. January 2016–present. www.sykestaxlaw. com.

Gould & Ratner LLP, Chicago, IL. Partner in Tax and Litigation Departments. Nationwide federal-tax practice. May 2013 – December 2015.

Greenberg Traurig LLP, Chicago, IL. Shareholder in Tax and Litigation Departments. Nationwide federal-tax practice. April 2010-April 2013.

McDermott Will and Emery LLP, Chicago, IL. Partner in Tax Department. Nationwide federal-tax practice. August 2002-April 2010

Scribner, Hall & Thompson LLP, Washington, DC. Partner. Nationwide federal-tax practice. November 1998-July 2002.

U.S. Department of Justice, Tax Division, Washington, DC. Rose to Assistant Section Chief (GM-15), after five competitive-service promotions. Outstanding Attorney awards in 1986, 1988, 1991, and 1997. Litigated federal tax cases in DC and across the nation. November 1984-October 1998.

U.S. Department of Justice, Madison, WI. Assistant U.S. Attorney and federal prosecutor. March 1982-October 1984.

District Attorney’s Office, Barron, WI. Assistant District Attorney and then District Attorney (prosecutor and municipal counsel). Appointed DA by Wisconsin Governor and later elected in contested election. October 1979-March 1982.



The Ohio State University, Moritz College of Law, Columbus, OH. J.D., June 1979. Student contribution published at flagship 41 Ohio St. L.J. 211 (1980).
University of Wisconsin–Eau Claire, Eau Claire, WI. B.A., magna cum laude, August 1976. History major, Philosophy minor.


• Admitted to the bars in Wisconsin (1979), DC (1998), and Illinois (2002), and many federal courts, including six federal appellate courts, the Court of Federal Claims, the U.S. Tax Court, and the U.S. Supreme Court. Member of Trial Bar of N.D. IL.
• Listed, Legal 500, 2007, 2009 (mentioning IRS’s full concession in bet-the-company case in Tennessee), and 2010. Leading Lawyer (Illinois) in Business Tax (top 5%). Illinois Super Lawyer in Tax (top 5%), 2005, 2007, 2010-2011, 2013-2021. Recipient of four Tax Division, DOJ, Outstanding Attorney Awards. Twice promoted by DOJ into non-political, competitive, supervisory positions (GM-15), including Assistant Chief.
• Extensively published, including Big Ten flagship law review. Co-author/revisor of (a) BNA/Bloomberg’s TMP 524, Deductibility of Illegal Payments, Fines, and Penalties; (b) BNA’s Tax Practice Series addressing Audits, Assessments, and Appeals; and (c) a supplement to the tax-shelter chapter of a definitive WG&L tax treatise (unacknowledged contribution).
• Extensively quoted in tax and non-tax publications.
• Author of the first ever published article on litigation finance for tax cases.
• Author, “The ‘Corporation’ Exception to Carried Interest: A Litigator’s View,” 169 Tax Notes Federal 769 (Nov. 2, 2020).

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Law Offices of Thomas D. Sykes PLLC

16625 Redmond Way Ste. M #151, Redmond, WA, 98052, US