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Thomas D. Sykes


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About me

Practicing on Chicago's North Shore, Tom has one of the nation's premier tax-dispute resumes.  For over 30 years, he has first-chaired tax controversies at the highest reaches of the profession.  During the first half of his tax career, he represented the IRS in tax disputes across the nation; during the second half, he represented many institutions that are household names while a partner or shareholder with two of the nation's most prestigious law firms.  He spent 18 years practicing tax law in Washington, D.C. before moving to Chicago in 2002.  Tom has tried 25 jury trials, handled over 200 non-jury tax cases, and handled a dozen appeals in the federal courts of appeals.  He is a former federal prosecutor and former state prosecutor.  He is extensively published and cited -- a "thought leader."  He may properly be regarded as having a "360-degree" tax-dispute resume.   He currently is litigating several cases seeking tens of millions of dollars in additional interest for some of the nation's most prestigious teaching hospitals -- institutions for which he was instrumental in securing a global concession from the IRS in 2010.    


Practice areas


  1. Tax: 35%
    34 years, 250 cases
  2. Litigation: 20%
    36 years, 325 cases
  3. Appeals: 15%
    34 years, 30 cases
  4. Administrative Law: 10%
    34 years, 50 cases
  5. Other: 20%
  6. More 



Hourly ($400-675/hour)

Payment types:


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Contact info

The Law Offices of Thomas D. Sykes LLC

825 South Waukegan Road #10
Lake Forest, IL, 60045


ILActive And Authorized To Practice Law200205/17/2016
DCActive 199807/06/2016
WIGood Standing197903/02/2015
MNNot Authorized - Non-payment of fees198106/15/2016
We have not found any instances of professional misconduct for this lawyer.
Avvo contributions
Legal answers
Award nameGrantorDate granted
Illinois Super LawyerSuper Lawyers Magazine2016
Illinois Super LawyerSuper Lawyers Magazine2015
Illinois Super LawyerSuper Lawyers Magazine2014
Illinois Super LawyerSuper Lawyers Magazine2013
Leading LawyerLeading Lawyers Network2012
Illinois Super LawyerSuper Lawyers Magazine2011
IdentifiedLegal 5002011
Leading LawyerLeading Lawyers Network2011
Illinois Super LawyerSuper Lawyers Magazine2010
IdentifiedLegal 5002010
Achievement MentionedLegal 5002007
Illinois Super LawyerSuper Lawyers Magazine2007
Illinois Super LawyerSuper Lawyers Magazine2005
Outstanding AttorneyU.S. Department of Justice1998
Outstanding AttorneyU.S. Department of Justice1991
Outstanding AttorneyU.S. Department of Justice1988
Outstanding AttorneyU.S. Department of Justice1986
ListedWho's Who In American LawN/A
Work experience
TitleCompany nameDuration
MemberThe Law Offices of Thomas D. Sykes LLC2016 - Present
PartnerGould & Ratner LLP2013 - 2015
ShareholderGreenberg Traurig LLP2010 - 2013
PartnerMcDermott Will & Emery LLP2002 - 2010
PartnerScribner Hall & Thompson LLP1998 - 2002
Assistant Chief, Reviewer, Senior Trial Attorney, etc.U.S. Department of Justice, Tax Division1984 - 1998
Assistant U.S. AttorneyU.S. Attorneys Office, Madison, WI1982 - 1984
District AttorneyBarron County District Attorneys Office1980 - 1982
Association namePosition nameDuration
Appellate Lawyers AssociationN/A2014 - Present
American Bar AssociationN/A2011 - Present
Federalist SocietyBoard Member, Chicago Lawyers Chapter2003 - Present
District of Columbia BarN/A1998 - Present
State Bar of WisconsinN/A1979 - Present
Legal cases
Case nameOutcome
The University of Chicago Hospitals v. United StatesWin
National Health Corporation v. United StatesWin
Wichita Center for Graduate Medical Education, Inc. et al. v. United StatesJust recently filed.
See all legal cases 
Publication nameTitleDate
Journal of AccountancyTen Situations in Which a CPA Should Call "Timeout"2015
CFO MagazineRuling Favors Employer Tax Refunds on Layoffs2012
BNA Daily Tax ReportThe Mayo Decision;s Problematic Tax Analysis2011
Health Lawyers Weekly (AHLA)Update On Next Steps For Teaching Hospitals To Recover FICA Tax Paid On Stipends Paid To Medical Residents2010
Health Lawyers Weekly (AHLA)IRS Concedes That Medical Resident Stipends are Not Subject to FICA Taxes for Quarters Before April 1, 2005: Now What?2010
American Bar Association, Criminal Litigation NewsletterNavigating Voluntary Disclosure in the Wake of the Government’s Assault on Undisclosed Foreign Accounts2009
BNA Portfolio No. 524Deductibility of Bribes, Kickbacks, Illegal Payments, Fines, and Penalties2007
Legal TimesWhose Tax Law Is It?2006
IP Law360To Practice Law, You Need a Patent License2006
BNA's Tax Practice SeriesChapter 3850, Examinations: Audits, Assessments, Appeals2005
The Tax ExecutiveThe Growing Controversy over Federal Excise Tax on Long-Distance Calls2003
Tax NotesThe Invalidity of the "For Everyone or No One" Rule, and a Tax-Recovery Strategy Suggested by the Analysis2003
Tax NotesPowerful New Arguments Against the Duplicated-Loss Provisions of the LDR2001
41 Ohio St. L.J. 211Chart v. General Motors: Did It Chart the Way for Admission of Evidence of Subsequent Remedial Measures?1980
School nameMajorDegreeGraduated
Ohio State University Moritz College of LawLawJD - Juris Doctor1979
University of Wisconsin, Eau ClaireHistoryBA - Bachelor of Arts1976
Speaking engagements
Conference nameTitleDate
Webcast, American Bar Association, Business Law SectionRecent Judicial Developments Respecting Chevron Deference2016
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 74022012
Third Annual Institute on the Ethics of Tax Law Practice, John Marshall Law SchoolShrinking Privileges, Expanding Responsibilities2010
NACUBO Tax ForumMedical Resident FICA2010
Ernst & Young ConferenceMedical Resident FICA and Other Employment Tax Issues2010
29th Annual Federal Tax Institute, Chicago-Kent College of LawRecent Development in Taxation2010
Tax Executives Institute's International Tax ForumInternational Compliance Issue2009