Caroline D. Ciraolo

Caroline D. Ciraolo

Washington, DC recognized lawyers icon Recognized in Best Lawyers since 2011
Kostelanetz LLP

14 Best Lawyers awards

Kostelanetz LLP logo

Awarded Practice Areas

Litigation and Controversy - Tax Criminal Defense: White-Collar Tax Law
*Named the "Lawyer of the Year" in this practice area in the 2026 edition in Washington, D.C..

Biography

Caroline D. Ciraolo, former Acting Assistant Attorney General of the U.S. Department of Justice’s Tax Division, is a partner with Kostelanetz LLP and a 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 related tax advice, conducting internal investigations, and representing individuals and entities in criminal tax investigations and prosecutions. Caroline is the former President of the American College of Tax Counsel and past Chair of the ABA Tax Section’s Civil and Criminal Tax Penalties Committee. She is a recipient of the IRS Chief Counsel Award and the ABA Tax Section’s Janet Spragens Pro Bono Award. She has served as an instructor with the IRS Military Volunteer Income Tax Assistance program at Ft. George G. Meade in Maryland. Caroline serves as an Adjunct Professor at the Georgetown University Law Center (Criminal Tax Law & Procedure and International Tax Controversies) and the University of Baltimore School of Law Graduate Tax Program (Investigation, Prosecution, and Defense of Tax Crimes and Tax Practice & Procedure). Caroline has been recognized by Chambers USA, The Legal 500, International Tax Review/World Tax, Best Lawyers in America, Super Lawyers, and The Daily Record’s Top 100 Women Circle of Excellence.

Kostelanetz LLP

14 Best Lawyers awards

Kostelanetz LLP logo

Overview

  • College of New Jersey, BA , graduated 1990
  • University of Baltimore, LL.M in Tax, graduated 1994
  • University of Maryland, J.D., graduated 1993

  • Maryland, Maryland State Bar Association
  • District of Columbia, The District of Columbia Bar
  • New Jersey, New Jersey State Bar Association
  • Pennsylvania, Pennsylvania Bar Association

  • Georgetown University Law Center - Graduate Tax Program, Adjunct Professor
  • University of Baltimore School of Law - Graduate Tax Program, Adjunct Professor
  • ABA, Section of Taxation - Immediate Past Chair (2019-2021), Civil and Criminal Tax Penalties Committee
  • ABA, Section of Taxation - Vice Chair, Membership, Diversity, & Inclusion (2021-2024)
  • American College of Tax Counsel - President (2021-2022)
  • MSBA, Taxation Section - Former Chair (2008-2009)
  • Maryland Bar Foundation - Fellow
  • CCH Journal of Tax Practice & Procedure - Member, Advisory Board
  • Military Volunteer Income Tax Assistance (VITA) Program - Instructor, Fort George G. Meade, Fort Meade, MD
  • Barrister's Club - Member
  • Rule Day Club - Member
  • Serjeant's Inn - Member
  • U.S. Tax Court Inn of Court - Member
  • U.S. Naval Academy Sponsor Program - Sponsor
  • Women's White Collar Defense Organization - Member

  • US Tax Court
  • US Court of Federal Claims
  • US Court of Appeals, Fourth Circuit
  • US Court of Appeals, Federal Circuit
  • US Supreme Court

  • United States Tax Court
  • Maryland, Maryland State Bar Association
  • District of Columbia, The District of Columbia Bar
  • New Jersey, New Jersey State Bar Association
  • Pennsylvania, Pennsylvania Bar Association
  • Georgetown University Law Center - Graduate Tax Program, Adjunct Professor
  • University of Baltimore School of Law - Graduate Tax Program, Adjunct Professor
  • ABA, Section of Taxation - Immediate Past Chair (2019-2021), Civil and Criminal Tax Penalties Committee
  • ABA, Section of Taxation - Vice Chair, Membership, Diversity, & Inclusion (2021-2024)
  • American College of Tax Counsel - President (2021-2022)
  • MSBA, Taxation Section - Former Chair (2008-2009)
  • Maryland Bar Foundation - Fellow
  • CCH Journal of Tax Practice & Procedure - Member, Advisory Board
  • Military Volunteer Income Tax Assistance (VITA) Program - Instructor, Fort George G. Meade, Fort Meade, MD
  • Barrister's Club - Member
  • Rule Day Club - Member
  • Serjeant's Inn - Member
  • U.S. Tax Court Inn of Court - Member
  • U.S. Naval Academy Sponsor Program - Sponsor
  • Women's White Collar Defense Organization - Member
  • College of New Jersey, BA , graduated 1990
  • University of Baltimore, LL.M in Tax, graduated 1994
  • University of Maryland, J.D., graduated 1993
  • US Tax Court
  • US Court of Federal Claims
  • US Court of Appeals, Fourth Circuit
  • US Court of Appeals, Federal Circuit
  • US Supreme Court
  • United States Tax Court

Client Testimonials

I have collaborated with Caroline on several conferences and panel presentations and she is a pleasure to work with. Her energy, dedication, and professionalism are first rate.

Caroline D. Ciraolo who focuses on federal and state civil tax controversies, including the representation in sensitive audits, and criminal tax defense, is not only extremely experienced and knowledgeable but also highly efficient in negotiating both excellent and comprehensive solutions for her clients.

Awards & Focus

Lawyer of the Year Badge - 2026 - Litigation and Controversy - Tax Lawyer of the Year Badge - 2025 - Tax Law Lawyer of the Year Badge - 2024 - Litigation and Controversy - Tax Lawyer of the Year Badge - 2022 - Litigation and Controversy - Tax Lawyer of the Year Badge - 2012 - Litigation and Controversy - Tax
Named "Lawyer of the Year" by Best Lawyers® for:
  • Litigation and Controversy - Tax, Washington, D.C. (2026)
  • Tax Law, Washington, D.C. (2025)
  • Litigation and Controversy - Tax, Washington, D.C. (2024)
  • Litigation and Controversy - Tax, Washington, D.C. (2022)
  • Litigation and Controversy - Tax, Baltimore (2012)
Recognized in The Best Lawyers in America® 2026 for work in:
  • Criminal Defense: White-Collar
  • Litigation and Controversy - Tax
  • Tax Law
Awards:
  • Baltimore SmartCEO Magazine's Legal Elite (2009, 2010)
  • Benchmark: America's Leading Litigation Firms and Attorneys (2013 - 2014)
  • Chambers USA, Nationwide: Tax Fraud (Band 1), DC: Tax (Band 2)
  • DC Super Lawyers (Tax) (2019-2022)
  • Featured in CNN Money Magazine -- 2013 Money Hero (April 2013)
  • Featured on cover of Maryland Super Lawyers Magazine (2013), and in featured article (2018)
  • IRS Office of Chief Counsel Award (2017)
  • Janet R. Spragens Pro Bono Award, ABA Section of Taxation (2010)
  • Judge, Janet R. Spragens Pro Bono Award, ABA Section of Taxation (2012-13)
  • Judge, Law Student Tax Challenge, ABA Section of Taxation (2011-14)
  • Judge, Public Service Fellowship, ABA Section of Taxation (2011-13)
  • Martindale-Hubbell® Bar Register of Preeminent Women Lawyers™
  • Legal 500 (Leading Lawyer, 2021)
  • Maryland Super Lawyers (Tax) (2009-2015, 2020-2022); Top 10 Attorneys in Maryland (2013 – 15); Top 25 Women Attorneys in Maryland (2009 - 11); Top 50 Women Attorneys in Maryland (2012 - 15); Top 100 Attorneys in Maryland (2010 - 15)
  • Maryland Volunteer Lawyers Service Educator Award (2008)
  • Recognized as a Top Tax Lawyer by Washingtonian (2017-2021)
  • Recognized as a Women in Tax Leader by International Tax Review (2017-2021)
  • The Daily Record’s Circle of Excellence (Women in Maryland) (2014)
  • The Daily Record's Top 100 Women in Maryland (2010, 2012, 2014)
  • US Tax Court Pro Bono Program, Maryland State Bar Association – Founder (2008/2009), Coordinator (2008-10), Volunteer (2008-14)

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