Caroline D. Ciraolo
Partner, Kostelanetz & Fink
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 tax tribunals, providing related tax advice, including advice on uncertain tax positions, financial reporting, claims for refund, amended returns, voluntary disclosures, and internal investigations, and representing individuals and institutions in criminal tax investigations and prosecutions.
During her tenure with the 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. accountholders, 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 statues 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 a Fellow and Regent of the American College of Tax Counsel, a recipient of the ABA Section of Taxation’s Janet Spragens Pro Bono Award, and 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, Benchmark, Best Lawyers in America, Super Lawyers (Top 10 Attorneys in Maryland, and 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. In January, 2017, Caroline was recognized by IRS Chief Counsel William Wilkens with the Chief Counsel Award, the highest honor that can be conferred by that office.
Caroline served as an Attorney Advisor for the Honorable Stanley J. Goldberg of the U.S. Tax Court from 1994 to 1996.