Thomas D. Sykes
16625 Redmond Way Ste. M #151
Redmond, WA 98052
Thomas D. Sykes
A Singular Federal Tax-Dispute Lawyer
In the nation’s industrial, legal, tax, and political power centers, Tom built a singular, premier, large-dollar, 360-degree federal-tax trial and appellate resume. After starting his legal career as a Wisconsin District Attorney and then 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. As a DOJ–Tax Division senior attorney, “chased bad guys” and worked revenue-heavy and highly technical cases involving issues of first impression. Went into private practice in 1998, when he joined a DC tax boutique as a partner, litigating federal tax 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 some of its wealthiest individuals and families. Led the charge, nationwide, in the successful effort to recover 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 — a concession leading to FICA tax refunds approaching $2bn. First-chaired a “most unusual” full-concession from DOJ and IRS of a $15mm bet-the-company, prohibited-transaction penalty case the Southeast. 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 to $600mm federal-tax class action for about 300 nonprofit teaching hospitals (concluded in 2019). Among other accolades (below), Tom is a thirteen-time, peer-selected Illinois Super Lawyer in Tax (top 5%), including 2013-2021. He has been repeatedly selected as one of Illinois’ top 100 high-stakes litigators (all types of cases). Followed spouse’s career to Seattle area in August 2019.
Law Offices of Thomas D. Sykes PLLC, Lake Forest, IL, and, after August 2019, Redmond, WA. Managing member. Nationwide federal tax-dispute practice. January 2016–present.
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, often protecting as much as $1 billion. 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. In 1981, while holding down the District Attorney position in Northwestern Wisconsin, passed the Minnesota Bar Exam without studying.
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.
BAR MEMBERSHIPS, AWARDS, SELECTED PUBLICATIONS
• 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, among several other U.S. district court admissions.
• Listed, Legal 500, 2007, 2009 (mentioning IRS’s “most unusual” full concession in the $15mm bet-the-company case), and 2010. Leading Lawyer (Illinois) in Business Tax (top 5% of all in that category in Illinois), many years, including 2019-2022. Illinois Super Lawyer in Tax (top 5% of all Illinois tax lawyers), 2005, 2007, 2010-2011, 2013-2021. Listed as one of Illinois’ Top 100 High Stakes Litigators by America’s Top 100 High Stakes Litigators (top one-half of one percent of all litigators of all types are so selected). Recipient of four Tax Division, DOJ, Outstanding Attorney Awards in 1986, 1988, 1991, and 1997. Twice promoted by DOJ’s Tax Division (in 1991 and 1997) into non-political, competitive, supervisory positions (GM-15), including Assistant Chief; assisted in supervising about 20 DOJ-Tax attorneys.
• Extensively published across four decades, including as a student in Big Ten flagship law review. Co-author/revisor of (a) BNA/Bloomberg’s TMP 524, Deductibility of Illegal Payments, Fines, and Penalties (definitive treatise); (b) BNA’s Tax Practice Series addressing Audits, Assessments, and Appeals; and (c) the supplement to the tax-shelter chapter of a definitive WG&L tax treatise (unacknowledged contribution). Most recently: “The ‘Corporation’ Exception to Carried Interest: A Litigator’s View,” 169 Tax Notes Federal 769 (Nov. 2, 2020); and, “New FinCEN Reporting Will Challenge Small Companies,” 174 Tax Notes Federal 149 (Jan. 10, 2022), and 103 Tax Notes State 149 (Jan. 10, 2022). Extensively quoted in tax and non-tax publications. Extensive speaking engagements on tax issues of the day.
Union League Club of Chicago, Resident Member (2003-2016); Sugar Island Association, Member (2004-2022).