LAWYER PROFILE
Caroline D. Ciraolo

Caroline D. Ciraolo

USA 2026

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Ranked in 3 practice areas

About

Provided by Kostelanetz LLP

Practice Areas

Tax Controversy; Tax Fraud; White Collar Criminal Defense

Career

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 disputes.

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 currently serves as the ABA Tax Section’s Vice Chair for Membership, Diversity, and Inclusion and 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.

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 University of Baltimore School of Law Graduate Tax Program (Tax Practice and Procedure).

Chambers Review

Provided by Chambers

Chambers Guide to the USA

Tax - District of Columbia

Band 1
Band 1

Individual Editorial

Caroline Ciraolo is a top choice for complex criminal and civil tax controversies. She brings to the table her valuable experience as a former employee of the DOJ Tax Division.

Tax: Controversy - USA - Nationwide

Band 1
Band 1

Individual Editorial
Caroline Ciraolo offers impressive governmental experience and is recognized for her adept representation of clients in high-profile criminal tax cases.

Tax: Fraud - USA - Nationwide

Band 1
Band 1

Individual Editorial
Caroline Ciraolo offers impressive governmental experience and is recognized for her adept representation of clients in high-profile criminal tax cases.

Strengths

Provided by Chambers

  • Caroline is incredibly smart and strategic. She integrates well into a team and is incredibly responsive.

    TaxChambers Guide to the USA
  • Caroline is the consummate professional and is well recognised for her deep tax knowledge but also for her client-focused approach.

    TaxChambers Guide to the USA
  • Caroline is a well-established leader in the tax controversy community. She is creative but careful in thinking through problems, loves to go deep into an issue and is thorough and efficient.

    TaxChambers Guide to the USA
  • Caroline is approachable and also very creative. She thinks about things from all angles.

    Tax: ControversyChambers Guide to the USA
  • Caroline is a total heavyweight in the criminal tax space.

    Tax: ControversyChambers Guide to the USA
  • Caroline cares deeply about her clients and spares no effort in attempting to get the best result for them.

    Tax: ControversyChambers Guide to the USA

Ranked Individuals at Kostelanetz LLP (14)

District of Columbia

Georgia

New York

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USA - Nationwide

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