Massey and Gail represents clients in federal tax litigation, as well as state and local tax controversies. We provide risk management advice to taxpayers during planning and audits and represent them in negotiations with local taxing authorities. Where disputes arise, we represent taxpayers in administrative proceedings, before state and federal tax courts, at trial, in mediation, and on appeal. Our team has handled cases across sectors, including financial services, technology, transportation, telecommunications, retail, and hospitality.

Our team includes the former general counsel and assistant general counsel for the Illinois Department of Revenue. Years of experience as tax administrators mean our lawyers have seen and understand the state and local tax issues our clients face. We also understand the priorities and objectives of state and local taxing authorities.

Because tax issues often present novel legal questions, our tax experts are experienced litigators in their own right who work hand-in-hand with our commercial litigation and appellate teams. Together, we provide strategic and innovative solutions to avoid and resolve tax controversies.

Representative matters include:

  • The firm represented a global financial institution in trial court and on appeal of an IRS audit disallowing over $200 million in tax credits for a cross-border loan transaction.
  • We represented an emerging technology company challenging local tax ordinances specifically targeting its business model.
  • We advised the Office of the Illinois Governor on constitutional and tax issues related to amending the Illinois Income Tax Act.
  • The firm litigated in trial court, appellate court, and before the Illinois Supreme Court the issue of where retailers are engaged in the “business of selling,” and to which jurisdiction they should remit sales tax.
  • We litigated in appellate court and before the Illinois Supreme Court whether capital projects of public utility entitled it to investment tax credits under Illinois law.
  • We litigated in appellate court and before the Illinois Supreme Court whether the state could tax full value of a corporate jet used in interstate commerce.