Tom has very extensive experience with federal payroll/employment/self-employment tax issues, having handled scores of court cases in this arena. This experience facilitates his advice on new Form 1099-NEC, to be used for reporting payments to independent contractors.
Tom has been called upon to provide advice on immigration matters and Social Security benefit matters. The latter is a natural adjunct to his extensive work on matters involving FICA and self-employment taxes, which support Social Security.
With the IRS now going forward with its promised High Net-Worth audits, Tom offers unusual assistance: he has handled both IRS administrative and litigation in this arena, as well as matters involving delinquent filings of foreign financial account reports, FinCen 114 (formerly known as Forms TD F 90-22.1), also known as FBARs. Resident aliens can find themselves surprised by the requirement that they file an FBAR, and Tom has successfully resolved those filing delinquencies for numerous clients. He thus has the experience necessary to transition seamlessly from audit, to IRS appeals, to federal trial courts, to federal appellate courts — and experience drawn from his years representing both high-net worth individuals and the IRS.
With a background as a former federal prosecutor, as a USDOJ Tax Division senior attorney and supervisor, and with extensive familiar with FinCEN’s foreign-bank-account reporting regime, Tom is superbly well situated to assist taxpayers who have failed to report income associated with virtual currency/cryptocurrency. A new reporting regime respecting beneficial ownership of an interest in domestic corporations and LLCs will arrive not later than January 2022. This will give the IRS a powerful new tool for detecting tax evasion. Taxpayers who have failed to report income should consult a tax attorney with a view to filing amended returns reflecting omitted income – and they should do so before the IRS comes knocking. Tom has extensive experience with the best ways to handle a failure to report income on federal tax returns.
Beginning in 2004, Tom was at the forefront of the landmark litigation over FICA tax paid on stipends provided to medical residents – litigation that in March 2010 led the IRS to announce a global concession of the issue. Tom first-chaired the landmark victories for The University of Chicago Hospitals in both the federal district court and then in the U.S. Court of Appeals for the Seventh Circuit. These victories were instrumental in prompting the IRS to announce its 2010 global concession. This reversal, by the IRS, of its long-time litigation position respecting an issue worth billions of dollars is one of the most notable reversals in IRS history. At the time of the IRS’s capitulation, Tom was lead counsel in more of the pending FICA-tax cases than any other attorney in the nation. He is the only attorney identified by The Legal 500 (2010 ed.) for work in this field. After working with many tax-exempt institutions to navigate the IRS’s implementation of its 2010 global concession, Tom concluded that most of these institutions had been denied the proper amount of interest on their refunds of employer-portion FICA tax. Again finding himself on the leading edge, Tom represented teaching hospitals seeking to recover seven or eight figures of additional statutory interest as a “follow on” to the FICA refunds made in 2012 or 2013 under the IRS’s 2010 global concession that he helped to secure. Tom is the only lawyer in the nation to have actively pursued additional interest in suits filed in federal court, filing his first suit of that type in July of 2013. That litigation was concluded in October 2019.
Tom has extensive familiarity with new Code section 1061(c)(4)(A) and IRS Notice 2018-18 — provisions restricting the tax benefits of Carried Interest, relevant to hedge fund managers. He is the only tax attorney in the nation to have litigated the scope and meaning of the critical “corporation” term found pervasively across about 600 Code Sections and in new section 1061(c)(4)(A). In that litigation, DOJ/IRS took incoherent positions that are inconsistent with the IRS’s announced view in Notice 2018-18. Opinions issued by the federal courts of appeals in those litigated cases, in which Tom filed over 20 briefs, reflect holdings about the “unambiguous” meaning of “corporation” that are fundamentally inconsistent with Notice 2018-18. Those briefs and courts of appeals opinions, which carried the day to deny the Nation’s tax-exempt, incorporated teaching hospitals hundreds of millions of dollars in statutory interest, are now expected to “boomerang” against the IRS in litigation brought by managers of S-corp hedge funds who wish to challenge Notice 2018-18 and the purportedly “clarifying” regulations it has recently proposed.
Recently, Tom reviewed the new Opportunity Zone legislation at the request of a potential investor.
Tom’s resume displays an intellectual bent. He is the co-author (revisor) of the definitive BNA Tax Management Portfolio (TMP) No. 524, Deductibility of Illegal Payments, Fines and Penalties, as well as co-author (revisor) of the chapter of BNA’s Tax Practice Series (TPS) that addresses IRS audits, assessments, and appeals. It includes a chapter on the Foreign Corrupt Practices Acts (FCPA), which has ever-increasing importance for companies with multinational operations. While a law student at Ohio State, he wrote an article on Wisconsin Rule of Evidence 407 that appeared in the Ohio State Law Journal, his law school’s flagship publication. Tom might be called a “thought leader:” over the years, he has published extensively, and his writings have been cited by the Supreme Court of Wisconsin; in several leading tax treatises; and in the American University Law Review, the Creighton University Law Review, the Marquette Law Review, the Nebraska Law Review, the Ohio State Law Journal, the University of Cincinnati Law Review, the University of Miami Law Review, the New York University School of Law Tax Law Review, and the University of Southern California Law Review. Tom is a frequent media quote source for prominent national publications addressing tax issues of the day.
Tom has long been professionally active with respect to a rapidly evolving field that has become critically important to tax professionals: the standards applicable to whether Treasury Regulations are authorized and valid, particularly under so-called Chevron Steps Zero, One, and Two. Tom published his first articles in this field back in 2001 (Chevron Step Zero) and 2003 (Chevron Step One). In 2011, he guided the briefing of a case that held a Treasury Regulation invalid under Step One. In a recent case, his Chevron-related arguments (all steps) prompted the U.S. Department of Justice to eschew, on brief in the Second Circuit, any reliance on a Treasury Regulation that had never been held invalid in any court — a move that is believed to be entirely without precedent. Tom has recently litigated cases presenting Chevron issues, including a class-action suit seeking about $500 million. Chevron will be involved in litigating cases challenging the government’s position as to new Code section 1061(c)(4)(A) set out in IRS Notice 2018-18 and the pending regulations.
In recognition of his tax-focused contributions, Tom recently was again named an Illinois Super Lawyer in Tax for 2020. Thirteen times Tom has been named an Illinois Super Lawyer in Tax (i.e., Top 5% as ranked by peers): 2005, 2007, 2010, 2011, 2013-2021. He is now listed among Washington state Super Lawyers. He has been named a Leading Lawyer in Tax Law–Business by the Leading Lawyers Network, including for 2019-2021 (again, Top 5%); and named a leading lawyer in the tax controversy field in the 2007 and the 2010 and 2011 editions of The Legal 500. While at the U.S. Department of Justice’s Tax Division in Washington, D.C., Tom received its Outstanding Attorney Award in 1986, 1988, 1991 and 1997, before leaving a GM-15 supervisory post for private practice in D.C. in 1998.
Tom formerly was a tax partner, or a tax shareholder, with the Chicago offices of two of the nation’s largest and most prestigious law firms. In addition, after leaving the U.S. Department of Justice’s Tax Division in 1998, after 14 years, he immediately became a partner with a “K Street” tax boutique in Washington, D.C. Tom’s nationwide federal tax practice thus brings with it the acumen and connections of a Washington-based “tax insider,” coupled with a complex-litigation resume of the highest order.
In short, Tom brings a classic, recognition-winning “big firm resume,” with an intense “360-degree” tax and complex-litigation perspective, to a smaller, more nimble, and extremely efficient boutique setting – one that is unencumbered by bureaucracy, firm-generated conflicts of interest, and expensive, rate-hiking foreign offices.