White Collar Defense and Investigations
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Francesca Ugolini

Phone: 202-998-2232

fugolini@southbank.legal

About Francesca

Francesca focuses her practice on federal tax advising and disputes, representing clients at every stage—from evaluating the risk of a tax return position to managing IRS audits and litigating in federal courts. She brings to her practice more than two decades of government experience and a deep understanding of both the technical tax landscape and the strategic considerations that drive effective dispute resolution.

Before joining SouthBank Legal, Francesca spent over 22 years at the U.S. Department of Justice’s Tax Division, including five years as the Chief of the Appellate Section. In that role, she directed all of the government’s civil tax litigation in the appellate courts and advised on trial strategy in the Tax Court, federal district courts, and the Court of Federal Claims. Earlier in her DOJ career, Francesca handled a broad and demanding docket involving numerous Fortune 500 companies. She has briefed more than 100 cases, supervised hundreds more, and argued over 60 in every federal circuit court. She also played a key role in over 15 tax cases before the U.S. Supreme Court.

Francesca began her career as a tax associate at an Am Law 100 firm, where she advised clients on corporate, tax-exempt, and international tax matters. Her experience reinforced a key insight she continues to carry in her practice today: companies and individuals want to get it right but face significant uncertainty in applying complex tax laws to real-world business decisions.

Francesca offers clients a rare combination of technical tax knowledge, seasoned litigation experience, and deep insight into the government’s approach to tax enforcement. Whether advising on novel, pre-filing tax issues or litigating refined legal questions, she brings a strategic, big-picture perspective designed to position clients for success as early—and as efficiently—as possible.

Experience

Francesca has worked on the full spectrum of tax issues affecting individuals, small businesses, tax-exempt organizations, and large companies. Here are some of her representative matters:

  • Transfer Pricing: Represented the government in a multi-million dollar case involving a medical device manufacturer and the comparable profits method for determining royalties. Represented the government in a transfer-pricing dispute with a Fortune 500 company involving the validity of a Treasury regulation under the Administrative Procedure Act and Loper Bright.
  • Economic Substance and Anti-Abuse Doctrines: Represented the government in numerous cases involving highly structured transactions where the IRS invoked judicial doctrines and anti-abuse provisions to disallow claimed tax benefits.
  • Individuals and Small Businesses: Represented the government in cases involving a wide array of tax deductions and credits, employment taxes, estate taxes, excise taxes, return-filing issues, tax and reporting penalties, cryptocurrency, interest netting, and collection issues (liens, levies, bankruptcy).
  • Energy Credits: Represented the government in cases involving a variety of energy tax credits and provided guidance to the Treasury Department on Inflation Reduction Act credits and regulations.
  • International Tax: Represented the government in cases involving Subpart F, U.S. residency, foreign tax credits, and treaty issues. Francesca was a key player in the government’s successful defense of I.R.C. 965 (mandatory repatriation tax) in the Ninth Circuit and U.S. Supreme Court.
  • FBAR Penalties: Represented the government in cases involving penalties for failure to report foreign bank accounts, including the standard for willfulness, reasonable cause defense, and whether a penalty is unconstitutionally excessive under the 8th Amendment.
  • IRS Audits: Represented the government in summons-enforcement proceedings involving privilege issues and cases involving the timeliness of an audit (statute of limitations).
  • After the government lost a case in the Ninth Circuit involving a partnership return claiming a $35 million loss, Francesca argued the case in an en banc rehearing against a renowned Supreme Court litigator and won. Watch the argument here.
  • Francesca was one of two Tax Division attorneys who assisted with the government’s defense of the Affordable Care Act, which the Supreme Court upheld under Congress’s taxing power. Francesca received the Attorney General’s Award for Exceptional Service – DOJ’s highest honor – for her contributions to the case.

Education

  • University of Virginia School of Law, J.D.
  • University of Maryland at College Park, B.S. in Mathematics, Honors Program, cum laude

Admissions

  • Maryland
  • District of Columbia
  • U.S. Tax Court
  • U.S. Court of Appeals for the D.C. Circuit
  • U.S. Court of Appeals for the First Circuit
  • U.S. Court of Appeals for the Second Circuit
  • U.S. Court of Appeals for the Fourth Circuit
  • U.S. Court of Appeals for the Fifth Circuit
  • U.S. Court of Appeals for the Ninth Circuit
  • U.S. Court of Appeals for the Tenth Circuit
  • U.S. Supreme Court