Representative Matters: National Validation

Home - Representative Matters: National Validation

A Singularity, Validated in a Roughly Estimated $4,000,000,000 of Cases First-Chaired in the Federal-Court “Crucible”


  • Tom’s name appears as counsel, almost always in a first-chair capacity, in more than 60 reported federal trial-court and appellate opinions.  He has first-chaired, or directly supervised, perhaps 250 tax cases in federal trial and appellate courts across the Nation, including many cases directly controlling over $100 million in tax and interest.  No attorney in the Pacific Northwest can make even half of this claim.
  • First-chaired Charleston Area Medical Center et al. v. United States, 940 F.3d 1362 (Fed. Cir. 2019).  Sought class-action certification on behalf of about 290 incorporated, tax-exempt teaching hospitals that were systematically paid a lower, non-standard rate of interest on refunds of employer-portion FICA tax made under the IRS’s 2010 global concession respecting FICA taxation of medical-resident stipends.  The suit sought to recover from the IRS an estimated $400 to $600 million dollars in additional statutory interest on behalf of members of the proposed class.  Tom was  the only attorney in the nation to have handled this type of suit.
  • First-chaired Wichita Center for Graduate Medical Education Inc. v. United States, 917 F.3d 1221 (10th Cir. 2019), addressing whether tax-exempt teaching hospitals are entitled to the standard rate of interest on prior refunds of overpaid employer-portion FICA tax.
  • First-chaired Medical College of Wisconsin Affiliated Hospitals, Inc. v. United States, 854 F.3d 930 (7th Cir. 2017), a case seeking $6.7 million in additional statutory interest on a prior refund of FICA tax.
  • First-chaired United States v. Detroit Medical Center, 833 F.3d 671 (6th Cir. 2016), a case seeking $9.1 million in additional statutory interest on a prior refund of FICA tax.
  • First-chaired Maimonides Medical Center v. United States, 809 F.3d 85 (2nd Cir. 2015), a case seeking $5.6 million in additional statutory interest on a prior refund of FICA tax.
  • Lead counsel in numerous cases presenting Chevron-deference issues. Recently, in an unprecedented move, the U.S. Department of Justice disclaimed reliance on a facially applicable Treasury Regulation in the face of Tom’s challenge to its validity.  Some years earlier, Tom guided the briefing of a case in which a federal district court held a Treasury Regulation invalid under Chevron Step One.
Orange sunset over Washington Monument and Lincoln Memorial viewed from Netherlands Carillion, Washington, D.C, U.S.A.
Orange sunset over Washington Monument and Lincoln Memorial viewed from Netherlands Carillion, Washington, D.C, U.S.A.
  • First-chaired The University of Chicago Hospitals v. United States, 545 F.3d 546 (7th Cir. 2008) — a tax-refund suit in which the U.S. Court of Appeals for the Seventh Circuit held,  wholly in favor of the teaching hospital with respect to FICA tax on stipends paid to medical residents — a holding that affirmed the favorable holding of the U.S. District Court below, also first-chaired by Tom.  Recovered $38 million for this teaching hospital and its residents.  Huge implications for hundreds of pending claims and cases worth between and $1 billion and $2 billion.
  • Lead counsel for Partners Healthcare System (i.e., Mass General Brigham) in a suit in Boston addressing whether $23 million in FICA tax must be repaid to the IRS in connection with stipends paid to medical residents — an issue that the IRS ultimately fully conceded.
  • Represented a billionaire before the IRS in connection with charitable multi-million dollar deduction taken for a gift to a donor-advised fund.
  • Primary responsibility for handling a Tax Court case in which the IRS agreed to reduce tax and penalty deficiencies to less than $6,000 from $839,000.
  • Lead counsel representing a partner in U.S. district court and in the U.S. Court of Appeals for the Seventh Circuit in a case of first impression under the unified partnership audit and litigation procedures of the Internal Revenue Code.
  • Key responsibility for obtaining a full and unqualified concession from the IRS in a Tax Court case of an issue worth $75 to $100 million to a large insurance company.
  • First-chaired, and settled on favorable terms, an estate tax case in which IRS challenged the bona fides of a family limited partnership (FLP).
  • First-chaired an administrative proceeding in which IRS reversed its view that a refund claim, seeking a recovery of more than $3 million, was procedurally defective.
  • First-chaired a two-day trial before an Illinois Department of Revenue Administrative Law Judge addressing whether a major facility owned by a tax-exempt entity was exempt from property taxes under the Illinois statutory exception for charitable and benevolent properties.
  • First-chaired the defense of an owner of a chain of tax-preparation stores in a case in which the IRS sought an injunction permanently barring the individual from involvement with tax-return preparation.
  • Advised more than 20 persons, both U.S. citizens and resident aliens, holding foreign financial accounts that had not been properly reported to the IRS (on FBARs), on how to belatedly bring themselves into compliance while minimizing penalties — with wholly successful results.
  • Assisted an international business that was not in compliance with federal tax laws, and against which a FinCEN Suspicious Activity Report (SAR) had been filed, in belatedly bringing itself into compliance with federal tax laws.
  • First-chaired a “bet the ESOP” case in U.S. district court in the Southeast in which the IRS and the Department of Justice completely conceded $15 million of excise tax and penalties in connection with a purported prohibited transaction. The case was described in The Legal 500’s law-firm survey for 2009 as reflecting a taxpayer-favorable result that was “most unusual.”
  • Represented the IRS, virtually always in a first-chair capacity, in cases in U.S. District Courts located in Wisconsin, Minnesota, Iowa, Missouri, Nebraska, Kansas, South Dakota, Montana, Colorado, Wyoming, Nevada, Arizona, and California, from 1984 to 1989.  For example, won a case, tried over the course of a week before the late, renowned Edward J. Devitt, U.S. District Judge, against a brother-sister/lawyer-CPA team, who made fraudulent conveyances for Minnesota landowners to defeat the collection of federal income-tax liabilities.  In the same court, in 1989, Tom was entrusted by the Department of Justice, representing the IRS, with the first-chair in a multi-million dollar gift-tax case in federal court in Minnesota, brought by heirs to the 3M fortune.  The case went to the Court of Appeals for the Eighth Circuit and then to the U.S. Supreme Court, where the IRS was victorious.  United States v. Irvine, 511 U.S. 224 (1994).  In a case in Milwaukee brought by Marquette University seeking a refund of FICA taxes paid, Tom, representing the IRS, won summary judgment on both of the issues, which pertained to payments made to faculty members for fellowships and awards.
  • Represented the IRS, either in a first-chair or supervisory capacity, in cases in the Court of Federal Claims (Washington, D.C.), and in the U.S. Court of Appeals for the Federal Circuit (Washington, D.C.), from 1989 to 1998.  For example, won a case (European American Bank v. U.S.), in both the Court of Federal Claims and later in the U.S. Court of Appeals for the Federal Circuit, that addressed $20 million in worthless debt deductions claimed by a large NYC bank with respect to oil production payment loans.  A first-chair, personal case load that for years sought to protect almost $1 billion in the aggregate.
  • As an Assistant U.S. Attorney, represented the United States and its departments, agencies, bureaus, offices, and officers in the U.S. District Court for the Western District of Wisconsin, and in the U.S. Court of Appeals for the Seventh Circuit (Chicago), from 1982 through 1984. First-chaired criminal and civil cases.  Tried eight criminal jury trials to a verdict, and briefed and argued several cases, including criminal cases, to the U.S. Court of Appeals for the Seventh Circuit.

Premier Experience — National Stature 


Note: These representations mostly occurred in the 34-year period before Tom established his own law firm in January 2016.

Get in Touch

Law Offices of Thomas D. Sykes PLLC

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

Contact Tom:

(847) 651-7881