Caroline Ciraolo, former Acting Assistant Attorney General of the U.S. Department of Justice’s Tax Division, is a partner with Kostelanetz LLP and founder of its Washington, D.C. office. Her practice focuses on federal and state civil tax controversies, including representation in sensitive audits, administrative appeals, and litigation, providing tax advice, conducting internal investigations, and representing individuals and entities in criminal tax investigations and prosecutions. She also serves as a consulting and testifying expert witness and an independent mediator in tax-related administrative proceedings and litigation.
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.
Caroline is former President of the American College of Tax Counsel and former Chair of the Civil & Criminal Tax Penalties Committee of the American Bar Association (“ABA”) Section of Taxation. She served as the ABA Tax Section’s inaugural Vice Chair for Membership, Diversity, and Inclusion, and inaugural Chair of the Loretta Collins Argrett Fellowship Program. Caroline also served as an instructor with the IRS Military Volunteer Income Tax Assistance program at Ft. George G. Meade.
She is recognized by Chambers (USA: Tax Fraud (Nationwide) (Band 1), Tax Controversy – Nationwide (Band 2), Tax (DC) (Band 1), High Net Worth: Tax-Private Client – USA (Band 1)); Legal 500 (Leading Lawyer); Benchmark Litigation; Best Lawyers in America (Litigation and Controversy – Tax, Tax Law, and Criminal Defense: White Collar; Lawyer of the Year – Litigation and Controversy – Tax (DC – 2022, 2024, and 2026, MD – 2012); Lawyer of the Year – Tax Law (DC – 2025)); ITR World Tax (Tax Controversy, World Tax – Highly Regarded and Women in Tax Leader); Super Lawyers (DC (Tax), Maryland (Tax), Top 10 in Maryland, Maryland cover story in 2013), 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, the IRS Chief Counsel Award, the highest honor that can be conferred by that office, and the Tax Excellence Award from the Taxation Section of the Maryland State Bar Association.
Caroline is an Adjunct Professor at the Georgetown University Law Center (International Tax Controversies and Criminal Tax Law and Procedure) and taught at the University of Baltimore School of Law Graduate Tax Program (Tax Practice and Procedure and Criminal Tax).
