Thomas D. Sykes | Nationwide Federal-only Tax Practice

Thomas Sykes Lawyer

Thomas D. Sykes update listing

Nationwide Federal-only Tax Practice

Tax, Tax Litigation, Income Tax


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I recently relocated my tax practice, started five years ago, from Chicago to the Seattle area.  I practiced tax law in Illinois for 18 years, and before that I practiced in DC for 18 years.  I both locations, I won recognition from my peers:  At the U.S. Department of Justice’s Tax Division in DC, I won Outstanding Attorney awards four times, and was twice promoted into competitive GM-15 supervisory positions.  In Illinois, I was peer-selected as an Illinois Super Lawyer in Tax 12 times, including in 2019 and 2020.  This recognition goes to the top five percent of Illinois lawyers.  I was repeatedly named an Illinois Leading Lawyer in Business Tax, also peer-selected and going to the top five percent.  My experience over my 36+ years of practicing tax law is almost evenly balanced between representing the IRS and representing private companies and persons.  I have represented or advised some of the nation’s largest and most prestigious corporate entities, and some of the nation’s wealthiest and even notorious individuals.  My tax background is unusual because I also was a federal criminal prosecutor, allowing me to be adept at handling tax cases with possible criminal overtones; it is also unusual because I have first-chaired over 20 jury trials and 15 cases in the federal courts of appeals, among the hundreds of tax cases I have first-chaired.  I now bring these very unusual, “360 degree” accomplishments, obtained in two of the nation’s top cities for a sophisticated tax practice, to the Seattle area.

I am available to handle any type of dispute a taxpayer, wherever located in the U.S., may have with the IRS.  In this day and age, a Seattle-area location is not a disadvantage in an IRS dispute.  Operating within the confines of my own law firm, the fees I charge can be very much lower than what a resume like mine would demand in the context of a mid-sized or Big Law firm.  I formerly was a partner and a shareholder with two of the nation’s largest and most prestigious law firms, so I know how their work is accomplished and their fees are structured.     

My career has been marked by a drive to understand the facts and law surrounding a dispute, and honing court-worthy arguments that will facilitate a settlement or, if the case cannot be settled, arguing the case to a federal court, both at the trial level and the appellate level, if necessary.  I almost certainly have more experience litigating sophisticated tax cases in federal trial and appellate courts than any tax attorney in the Pacific Northwest. When it comes to preparation, I believe in the old adage:  “if you want peace, prepare for war.”

My most recent notable engagements were representing many of the nation’s nonprofit teaching hospitals in a series of courts across the nation.  They were worth $500 to $600 million in additional interest on about $2 billion of FICA-tax refunds I had earlier been a national leader in obtaining.   Even though I knew the odds of winning were not great because of a poorly written statute that made no policy sense, the challenge was intriguing and rewarding because the clients could not have been more worthy.  Moreover, the tax issue was complicated and intellectually fascinating, and I had the opportunity to work with personnel from one of the nation’s largest accounting firms.

For her part, a taxpayer with a looming dispute with the IRS should look for a tax lawyer who has a strong ability understand federal tax law, which consists of 65,000 pages of statutes and regulations.  That ability must be coupled with an attention to factual detail, as even seemingly small points can sometimes make a difference.  Arriving at a position to take before the IRS is an iterative process of unearthing the relevant law and the relevant facts, and then fashioning a compelling argument and “story.”  But a tax lawyer is well advised not to make arguments that will be non-starters with the IRS and the courts.  Possessing over 36 years of experience at the highest levels of the tax profession permits me to make the judgments necessary for argument- and cost-effectiveness.  In a realm with this possible degree of complexity, what a client is hiring is (or should be)  judgment.   

My resume may suggest that I am one-dimensional, but far from it.  Beyond my family and my profession, my interests are golf, Chicago architecture, Frank Lloyd Wright’s architecture, antique furniture and glassware, U.S. history, and my genealogy and my wife’s.   

I am pleased to provide an initial phone consultation, even one going into considerable detail as I try to understand the client’s needs, at no charge.   
Position Organization Location Duration
AttorneyLaw Offices of Thomas D. Sykes PLLCRedmond, WAPresent
School Degree Major Graduation
Michael E. Moritz College of Law, Ohio State UniversityJ.D. Law School1979  
University of WisconsinBachelors1976
State / Court Date
Illinois2002
District of Columbia1998
Wisconsin1979
  • Member, Tax Advisory Board | John Marshall Law School | 2008-2014
    Member, Legal Committee and Safety Committee | Union League Boys & Girls Clubs of Chicago | 2011-Present
    Board of Governors | Court of Federal Claims Bar Association | 2001-2003
  • Profiled | The Ohio State University Moritz College of Law’s All Rise Magazine | Winter 2013
    Illinois Super Lawyer for Tax, 2005, 2007, 2010-2011, 2013-2020 — ranked by peers among Top 5% of Illinois Tax Lawyers (all types); Illinois Super Lawyer for Appellate | 2017
    Listed | The Legal 500, United States, 2007, 2010-2011.  In 2010, listed for practice in the medical-resident FICA field.
    Listed | Leading Lawyers Network (Illinois), Tax Law — Business (again, Top 5% as selected by peers), including for 2019 and 2020
    Rated “Superb” (10.0/10) among tax lawyers by the AVVO lawyer-rating website
    Outstanding Attorney Award, U.S. Department of Justice, Tax Division, Washington, D.C., 1986, 1988, 1991, 1997
    Promoted into ascending supervisory, civil-service positions (GM-15) at the Tax Division, U.S. Department of Justice, Washington, D.C., 1991 and 1997
  • Wichita Center for Graduate Medical Education, Inc. et al. v. United States | Just recently filed. The University of Chicago Hospitals v. United States | Win National Health Corporation v. United States | Win Various | Few losses; mostly wins and settlements.

  • Webcast, American Bar Association, Business Law Section | Recent Judicial Developments Respecting Chevron Deference | 2016
    ABA's Section of Taxation and Section of Real Property, Trust, and Estate Law (Boston, MA) | Litigation of Actions under Section 7408 and Related Sections, Such as Section 7407 and 7402 | 2012
    NACUBO Tax Forum | Medical Resident FICA | 2010
    29th Annual Federal Tax Institute, Chicago-Kent College of Law | Recent Development in Taxation | 2010
    Ernst & Young Conference | Medical Resident FICA and Other Employment Tax Issues | 2010
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Update Date: 2018-08-11

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Thomas D. Sykes
16625 Redmond Way
Ste. M #151
Redmond, WA 98052
47.672582,-122.1181623

MAIN LOCATION

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


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  • Tom has relocated his nationwide, federal-only tax practice from Chicago to the Seattle area.

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