About Caroline Ciraolo

Caroline D. Ciraolo, former Acting Assistant Attorney General of the U.S. Department of Justice’s Tax Division, is a partner with Kostelanetz & Fink and a founder of its Washington, D.C. office. Her practice focuses on complex and sophisticated civil tax controversies, including representation in sensitive audits, administrative appeals, and litigation in federal and state courts and administrative tax tribunals, providing related tax advice, conducting internal investigations, consideration of domestic and foreign compliance options including voluntary disclosures, and representing individuals and institutions in criminal tax investigations and prosecutions.

During her tenure with the Justice Department, Caroline was actively involved in all aspects of Tax Division operations and responsible for approximately 500 employees, including more than 360 attorneys in 14 civil, criminal and appellate sections. Under her leadership, the Division reached agreements with 80 Swiss financial institutions that admitted to facilitating tax evasion and the avoidance of reporting requirements by U.S. account holders, and imposed and collected more than $1.36 billion in penalties, increased civil and criminal enforcement with respect to offshore tax evasion, employment tax violations, and traditional tax offenses, assisted the IRS through summons enforcement proceedings, and engaged in affirmative and defensive litigation involving abusive tax shelters and schemes, refund claims, and challenges to statutes and regulations.

Prior to joining the Department, Caroline was Chair of the Tax Controversy and Litigation practice group of a regional firm in Baltimore, Maryland, where she represented individuals and businesses in all phases of state and federal civil tax controversies and criminal tax investigations and prosecutions. She has appeared before the IRS, the Comptroller of Maryland and the D.C. Office of Tax and Revenue, the Maryland Tax Court, the U.S. Tax Court, U.S. District Courts, the Maryland circuit and appellate courts and the U.S. Court of Appeals for the Fourth and Federal Circuits.

Caroline is President of the American College of Tax Counsel and Chair of the Civil and Criminal Tax Penalties Committee of the American Bar Association’s Section of Taxation. Caroline has also served as an instructor with the IRS Military Volunteer Income Tax Assistance program at Ft. George G. Meade in Maryland.

She has been recognized by Chambers (Tax Fraud (Nationwide), Tax (DC), Benchmark, Best Lawyers in America (Litigation and Controversy – Tax, Tax Law), Super Lawyers (Top 10 Attorneys in Maryland, Maryland cover story in 2013, DC), Euromoney Legal Media Group’s Americas Women in Business Law Awards (Best in Tax Dispute Resolution) (2014), and The Daily Record’s Top 100 Women Circle of Excellence. Caroline is a recipient of the ABA Section of Taxation’s Janet Spragens Pro Bono Award, and in January 2017, she was recognized by IRS Chief Counsel William Wilkins with the Chief Counsel Award, the highest honor that can be conferred by that office.

Caroline is an Adjunct Professor at the Georgetown University Law Center (International Tax Controversies, Criminal Tax Law and Procedure) and University of Baltimore School of Law Graduate Tax Program (Investigation, Prosecution and Defense of Tax Crimes).