Caroline D. Ciraolo

Caroline D. Ciraolo


Kostelanetz LLP

Recognized since 2011

Washington, District of Columbia

Practice Areas

Litigation and Controversy - Tax

Tax Law

Lawyer of the Year Badge - 2025 - Tax Law
Send Caroline D. Ciraolo an email at cciraolo@kostelanetz.com Navigate to map location for Caroline D. Ciraolo
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
Spinning circle Big letter B

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.

Location
  • 601 New Jersey Avenue, NW, Suite 260
    Washington, DC 20001
Education
  • College of New Jersey, BA , graduated 1990
  • University of Baltimore, LL.M in Tax, graduated 1994
  • University of Maryland, J.D., graduated 1993
Bar Admissions
  • Maryland, Maryland State Bar Association
  • District of Columbia, The District of Columbia Bar
  • New Jersey, New Jersey State Bar Association
  • Pennsylvania, Pennsylvania Bar Association
Affiliations
  • 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
Court Admissions
  • US Tax Court
  • US Court of Federal Claims
  • US Court of Appeals, Fourth Circuit
  • US Court of Appeals, Federal Circuit
  • US Supreme Court
Federal Clerkships
  • United States Tax Court

Kostelanetz LLP
Headquarters: New York, New York

13 The Best Lawyers in America® awards

2 Best Lawyers: Ones to Watch® in America awards

Visit Website View Firm Profile

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:
  • 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® 2025 for work in:
  • 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)
Additional Areas of Practice:
  • Criminal Defense: White-Collar

Spinning circle Big letter B

Publications

Your browser is not fully compatible with our automatic printer friendly formatting.

Please use the print button to print this profile page.

Spinning circle Big letter B