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Caroline D. Ciraolo

Caroline D. Ciraolo

Caroline D. Ciraolo

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Washington, D.C. | Baltimore, MD
T: 443.845.4898
F: 212.808.8108

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.  She has been recognized by Chambers (USA: Tax Fraud (Nationwide) (Band 1), Tax (DC) (Band 1), High Net Worth: Tax-Private Client – USA (Band 1)); Legal 500; Benchmark; Best Lawyers in America (Litigation and Controversy – Tax, Tax Law, Lawyer of the Year – Litigating and Controversy – Tax (DC – 2022 and 2024, MD – 2012)); 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 University of Baltimore School of Law Graduate Tax Program (Tax Practice and Procedure).

  • University of Baltimore School of Law, LL.M. in Taxation (1994)
  • University of Maryland, School of Law, J.D. (Honors) (1993)
  • The College of New Jersey, B.S. in Finance (Honors) (cum laude) (1990)
  • Maryland (1993)
  • Pennsylvania (1995)
  • New Jersey (1995)
  • District of Columbia (1995)
  • US Tax Court
  • US District Court, District of Maryland
  • US Court of Federal Claims
  • US Court of Appeals, Fourth Circuit
  • US Court of Appeals, Ninth Circuit
  • US Court of Appeals, Federal Circuit
  • US Supreme Court
  • Georgetown University Law Center, Adjunct Professor
    • International Tax Controversies
    • Criminal Tax Law and Procedure
  • University of Baltimore School of Law, Graduate Tax Program, Adjunct Professor
    • Tax Practice and Procedure
  • Co-Chair, D.C. Bar Tax Conference (2024 – present)
  • Co-Chair, Tax Controversy Forum, New York University School of Professional Studies (2022 – present)
  • Co-Chair, International Tax & Disputes, Cambridge Forum (2022 – present)
  • Tax Division, U.S. Department of Justice, Washington, DC
    • Acting Assistant Attorney General (February 25, 2015-July 15, 2016)
    • Principal Deputy Assistant Attorney General (January 12, 2015-January 20, 2017)
    • Deputy Assistant Attorney General for Criminal Matters (October 5, 2015-January 20, 2017)
    • Deputy Assistant Attorney General for Policy and Planning (January 12, 2015-January 20, 2017)
  • Attorney Advisor, Honorable Stanley J. Goldberg, U.S. Tax Court (August 1994-August 1996), Washington, DC
  • Fellow, American College of Tax Counsel
    • Immediate Past President (2021-2022)
    • Vice President (2020-2021)
    • Secretary/Treasurer (2018-2020)
    • Regent (4th Circuit) (2017-2018)
  • American Bar Association, Section of Taxation
    • Vice Chair of Membership, Diversity, and Inclusion (2021-present)
    • Civil and Criminal Tax Penalties Committee
      • Chair, (2019-2021)
      • Vice-Chair (2009-2014, 2017-2019)
      • Sub-Committee Chair – Important Criminal Developments (2004-2008)
    • Appointments to the Tax Court Committee (2019-present)
    • Nominating Committee (2011-2014, 2018-2019)
    • Public Fellowship Committee (2009-2013)
    • Pro Bono Award Committee (2012-2014)
  • Member, Serjeant’s Inn
  • Member, Rule Day Club
  • Member, Barrister’s Club
  • Fellow, Litigation Counsel of America
  • Fellow, Maryland Bar Foundation
  • Trustee, Baltimore Bar Foundation
  • MD State Bar Association: Taxation Section
    • Council (2001-2014)
    • Chair (2008-2009)
    • Chair-Elect (2007-2008)
    • Secretary/ Treasurer (2006-2007)
    • Tax Controversy Group, Founder
      • Chair (2004-2008)
      • Advisor (2009-2014)
  • Member, U.S. Tax Court Inn of Court
  • Member, Women’s White Collar Defense Association
  • Member, Network 2000
    • Co-chair, Women of Excellence Luncheon (2013-2014)
    • Member, Board of Directors (2014)
  • Member, Board of Directors, Maryland Volunteer Lawyer Service (2009-2014)
    • Chair, Annual Benefit (2012-2014)
  • Member, Board of Directors, Federal Bar Association (Maryland Chapter) (2014)
  • Member, Day 4 Committee (State and Local Tax), Advanced Tax Institute, Maryland State Bar Association and Maryland Association of CPAs (2006-2014)
  • Member, Advisory Board, Thomson West Tax (2007-2014)
  • Member, Tax Advisory Board, Wolters Kluwer (2013-2014)
  • Member, Advisory Board, CCH Journal of Tax Practice & Procedure (2011-2014)
  • Instructor, Military Volunteer Income Tax Assistance (VITA) Program, Fort George G. Meade, Fort Meade, Maryland (2012-2015, 2018)
  • Member, Advisory Board, Choice Jobs Program (2010-2015)
  • Member, Advisory Board, Fannie Angelos Program for Academic Excellence (2014)
  • Sponsor, U.S. Naval Academy Sponsor Program

Circular 230–Final Regulations and a New Principles-Based Approach, CCH’s Journal of Tax Practice & Procedure (JTP&P) (August-September, 2014)

The Ins and Outs of Federal Criminal Tax Cases, Maryland Bar Bulletin (April, 2014)

The Tax Man is Coming Bank: A Word of Warning to Liquor Retailers, The Barrister (December 2013/January 2014)

The Reasonable Cause Defense to Penalties and Some Good News for Taxpayers, CCH’s Journal of Tax Practice & Procedure (JTP&P) (August-September, 2013)

The FBAR Penalty: What Constitutes Willfulness?, Maryland Bar Journal (Taxation Issue, May-June, 2013)

The Eggshell Audit Part II: Indicators of Fraud and IRS Fraud Development Procedures, with Larry Campagna and Eric Green, JTP&P (February-March, 2013)

But I Relied on My Accountant! The Scope of the Reasonable Cause Defense to Penalties, co-authored with Larry Campagna and Ellis Reemer, JTP&P (August-September, 2012)

The Eggshell Audit Part I: A Primer, with Larry Campagna and Eric Green, JTP&P (June-July, 2012)

Criminal Tax Cases: A Primer, a chapter in Inside the Minds: Strategies for Criminal Tax Cases, Aspatore (2011)

Last Known Address, a chapter in the recently published, Effectively Representing your Client before the Internal Revenue Service, 5th Edition (ABA Section of Taxation (2011))

Frequently Charged Tax Crimes, Federal Public Defender National Conference (June, 2011)

Refund Claims and Claims for Contribution, ABA Section of Taxation (May, 2011)

Editor, A Practitioner’s Guide to Innocent Spouse Relief: Proven Strategies for Winning Section 6015 Tax Cases, by Robert B. Nadler (ABA Section of Taxation (2011))

FinCEN Issues Final FBAR Regulations, CCH JTP&P (April-May, 2011)

Ask the Professionals (Various Tax-Related Topics), Baltimore Business Journal (2010 – present)

The Morning After – What You Need to Know FBAR and International Information Returns Including Defending Against and Litigating the Penalties, JTP&P (October-November, 2009)

Attaching Property Held as Tenancy by the Entirety: The Response to Craft, JTP&P (January 1, 2004)

There are no upcoming events.

Federal Bar Association 2024 Tax Law Conference (CLE/CPE)

March 1 @ 8:00 am - March 5 @ 5:00 pm EST

60th Annual Hawaii Tax Institute Conference

November 5, 2023 - November 9, 2023

Please Sir, Can I Have Some Moore

October 27, 2023 @ 1:15 pm - 2:15 pm CDT

Tax Court Updates

October 26, 2023 @ 11:10 am - 11:50 am PDT

Tax Controversy – When The Line Is Crossed… (CLE)

September 21, 2023 @ 7:30 am - 9:00 am PDT
  • Panelist, From the Experts: Tax Controversy and Tax Litigation – Civil and Criminal Tax Update, 78th Institute on Federal Taxation, New York University, San Francisco, CA (November 10, 2019)
  • Panelist, What Every Estate Planner Needs to Know About International Tax and Reporting, and the Government’s Enforcement and Initiatives, 2019 Annual Meeting of the California Tax Bar & California Tax Policy Conference, San Diego, CA (November 8, 2019)
  • Panelist, IRS Voluntary Disclosure Program and Updates on the Other Offshore Procedures, 56th Annual Hawaii Tax Institute, Honolulu, Hawaii (November 5, 2019)
  • Panelist, Caution Trustees – Beware of Unresolved Tax Liabilities of Incapacitated Taxpayers and Decedents; Ethical Considerations, 56th Annual Hawaii Tax Institute, Honolulu, Hawaii (November 4, 2019)
  • Panelist, Paying U.S. Taxes in Canada: Are You Caught on the Borderline?, Pathways to US Tax, Windsor, OH, Canada (November 2, 2019)
  • Speaker, Recruiting and Retaining Women in Tax – What Does it Take, Tax Section of the Federal Bar Association, Washington, D.C. (October 25, 2019)
  • Speaker, The New Age of Voluntary Disclosures, Graduate Tax Scholars, Georgetown University Law Center, Washington, D.C. (October 24, 2019)
  • Panelist, IRS International Tax Enforcement in a Post-OVDP World, 15th Annual University of San Diego School of Law Procopio International Tax Institute, San Diego, CA (October 18, 2019)
  • Panelist, Identifying the Line Between Avoidance and Evasion: Global Criminal Tax Enforcement, 15th Annual University of San Diego School of Law Procopio International Tax Institute, San Diego, CA (October 17, 2019)
    Chaired, Civil and Criminal Tax Penalties, ABA Tax Section Fall 2019 (October 5, 2019)
    Speaker, What’s New in Federal Tax Enforcement?, The American Academy of Attorney-CPAs 2019 Annual Meeting & Education Conference (July 5, 2019)
  • Panelist, IRS Voluntary Disclosures: Past, Present, and Future, The American Academy of Attorney-CPAs 2019 Annual Meeting & Education Conference, Orange Beach, AL (July 5, 2019)
  • Interviewer, Department of Justice Update, NYU SCPS 11th Annual Tax Controversy Forum (June 21, 2019)
  • Moderator, How Well Do Your Secrets Travel? Understanding the Scope of Privileges in Crossborder Audits and Investigations, NYU SCPS 11th Annual Tax Controversy Forum (June 20, 2019)
  • Panelist, FBAR & FATCA: The Crackdown on Unreported Foreign Assets Continues, AICPA ENGAGE 2019 Conference (June 11, 2019)
  • Panelist, IRS Controversies, AICPA ENGAGE 2019 Conference (June 11, 2019)
  • Panelist, IRS Examinations and Appeals, The IRS Workshop, AICPA ENGAGE 2019 Conference (June 10, 2019)
  • Panelist, Addressing Conflicts of Interest in Today’s Tax Practice, Tax Alliance Conference, Dallas, TX (June 5, 2019)
  • Moderator, The Current State of the IRS, Personal Income Tax Committee, New York City Bar, New York, NY (May 28, 2019)
  • Moderator, Whistleblowers: Protections and Privacy, 4th International Conference on Taxpayer Rights, Minneapolis, MN (May 24, 2019)
  • Panelist, Parallel Proceedings, 3d Annual Lightfoot White Collar Institute, Birmingham, AL (May 8, 2019)
  • Panelist, What Every Estate Planner Needs to Know About International Tax and Reporting, and the Government’s
  • Enforcement and Initiatives?, California Lawyers Association Tax Section Annual Estate and Gift Tax Conference, San Francisco, CA (March 15, 2019)
  • Panelist, Updated Voluntary Disclosure Procedures: Is this the Correct Path for Your Noncompliant Client?, 43rd Annual Tax Law Conference, Federal Bar Association, Washington, DC (March 8, 2019)
  • Moderator, New Developments in Criminal Tax Enforcement, 33rd Annual National Institute on White Collar Crime, American Bar Association, New Orleans, LA (March 6, 2019)
  • Speaker, What’s New in Tax Enforcement – Current Priorities of the IRS and DOJ Tax Division, The Rule Day Club, Baltimore, MD (February 12, 2019)
  • Speaker, Criminal Tax Enforcement: What Lies Ahead in 2019, Georgetown Scholars Lunch, Georgetown University Law Center, Washington, DC (February 7, 2019)
  • Speaker, Current Developments – Tax Division, U.S. Department of Justice, 2019 ABA Taxation Section Midyear Meeting, New Orleans, LA (January 18, 2019)
  • Panelist, Tax Advice in the Age of the 24-Hour News Cycle, 2019 ABA Taxation Section Midyear Meeting, New Orleans, LA (January 18, 2019)
  • Keynote Speaker, Update from Washington, D.C., 37th Annual International Tax Conference, Tax Section, Florida Bar Association, Miami, Florida (January 10, 2019)
  • Chambers USA, Nationwide: Tax Fraud (Band 1), District of Columbia: Tax (Band 1)
  • Chambers High Net Worth, Tax-Private Client – USA (Band 1)
  • Legal 500 (Leading Lawyer, 2021-24)
  • Recognized as a Top Tax Lawyer by Washingtonian (2017-23)
  • Recognized as a Women in Tax Leader and World Tax – Highly Regarded by International Tax Review (2017-24)
  • IRS Office of Chief Counsel Award (2017)
  • The Daily Record’s Leadership in Law (2015)
  • Best Lawyers in America – Tax and Litigation & Controversy – Tax (2011-14, 2019-24); Lawyer of the Year, Litigation & Controversy – Tax (2022, 2024) (Washington, D.C.); Lawyer of the Year, Litigation & Controversy – Tax (2012) (Baltimore)
  • Best Lawyers, Business Edition – Women in Tax Law (2021)
  • Nominee (shortlist), Euromoney Legal Media Group’s Americas Women in Business Law Awards (Best in Tax Dispute Resolution) (2014)
  • DC Super Lawyers (Tax) (2019-24); Top 50 Women Attorneys in DC (2024)
  • Maryland Super Lawyers (Tax) (2009-15, 2020-24); Top 10 Attorneys in Maryland (2013-15); Top 25 Women Attorneys in Maryland (2009-11); Top 50 Attorneys in Maryland (2010-15)
  • Featured on the cover of Maryland Super Lawyers Magazine (2013) and featured article (2018)
  • Benchmark: America’s Leading Litigation Firms and Attorneys (2013-14)
  • Baltimore SmartCEO Magazine’s Legal Elite (2009, 2010)
  • Martindale-Hubbell® Bar Register of Preeminent Women Lawyers™
  • Janet R. Spragens Pro Bono Award, ABA Section of Taxation (2010)
  • The Daily Record’s Top 100 Women in Maryland (2010, 2012, 2014)
  • The Daily Record’s Circle of Excellence (Women in Maryland) (2014)
  • Maryland Volunteer Lawyers Service Educator Award (2008)
  • S. Tax Court Pro Bono Program, Maryland State Bar Association – Founder (2008/2009), Coordinator (2008-10), Volunteer (2008-14)
    • S. Tax Clinic Pro Bono Clinic – Co-Founder (2013), Volunteer (2013-14)
  • Judge, Public Service Fellowship, ABA Section of Taxation (2011-13)
  • Judge, Law Student Tax Challenge, ABA Section of Taxation (2011-14)
  • Judge, Janet R. Spragens Pro Bono Award, ABA Section of Taxation (2012-13)
Best Lawyers - Kostelanetz LLP 2024
Best Lawyers - Caroline D. Ciarolo 2024
Caroline D. Ciraolo - Chambers 2023
Caroline Ciraolo - Chambers 2022
Caroline Ciraolo - Chambers 2021
Caroline Ciraolo - Chambers 2020
Caroline Ciraolo - Chambers 2019
Caroline Ciraolo - Chambers 2018
Caroline Ciraolo - The Legal 500 2022
Caroline D. Ciarolo - Super Lawyers 2024
Caroline D. Ciraolo - Super Lawyers 2023
Caroline Ciraolo - Super Lawyers 2022
Caroline Ciraolo - Super Lawyers 2021
Caroline Ciraolo - Super Lawyers
Caroline Ciraolo - Super Lawyers
Caroline Ciraolo - Super Lawyers
Caroline D. Ciraolo - Top 50 Women
Caroline Ciraolo - Super Lawyers
Caroline Ciraolo - Super Lawyers
Caroline Ciraolo - Super Lawyers
Caroline Ciraolo - Super Lawyers