Caroline D. Ciraolo

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 administrative tax tribunals, providing related tax advice, conducting internal investigations, consideration of domestic and foreign compliance options including voluntary disclosures, and representing individuals and institutions in criminal tax investigations and prosecutions.

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. 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. account holders, 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 Officer of the American College of Tax Counsel and Chair of the Civil and Criminal Tax Penalties Committee of the American Bar Association’s Section of Taxation. Caroline has also 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 (Tax Fraud (Nationwide), Tax (DC)), Benchmark, Best Lawyers in America (Litigation and Controversy – Tax, Tax Law), Super Lawyers (Top 10 Attorneys in Maryland, Maryland cover story in 2013, DC), 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, and in January 2017, she was recognized by IRS Chief Counsel William Wilkins with the Chief Counsel Award, the highest honor that can be conferred by that office.

Caroline is an Adjunct Professor at the Georgetown University Law Center (International Tax Controversies) and University of Baltimore School of Law Graduate Tax Program (Investigation, Prosecution and Defense of Tax Crimes).


Government Experience

  • 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 Policy and Planning (January 12, 2015-January 20, 2017)
    • Deputy Assistant Attorney General for Criminal Matters (October 5, 2015-January 20, 2017)
  • Attorney Advisor, Honorable Stanley J. Goldberg, U.S. Tax Court (August 1994-August 1996), Washington, DC

Awards and Recognitions

  • Recognized as a Best Lawyers 2020 for Litigation and Controversy - Tax and Tax Law (Washington, D.C.) by U.S. News - Best Lawyers 2020
  • Chambers USA, Nationwide: Tax Fraud, District of Columbia: Tax
  • Recognized as a Top Tax Lawyer by Washingtonian (2017, 2018) 
  • Recognized as a Women in Tax Leader by International Tax Review (2017, 2018)
  • Recognized in Women in Tax Leaders Guide, 5th Edition, 2020
  • IRS Office of Chief Counsel Award (2017)
  • The Daily Record’s Leadership in Law (2015)
  • Best Lawyers in America - Litigation & Controversy – Tax (2011-14, 2019, 2020); Lawyer of the Year, Litigation & Controversy - Tax (2012) (Baltimore)
  • Nominee (shortlist), Euromoney Legal Media Group’s Americas Women in Business Law Awards (Best in Tax Dispute Resolution) (2014)
  • DC Super Lawyers (Tax) (2019)
  • Maryland Super Lawyers (Tax) (2009-15, 2020); 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)
  • Featured on the cover of Maryland Super Lawyers Magazine (2013); and featured article (2018)
  • Featured in CNN Money Magazine – Money Hero (April 2013)
  • 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)

Professional Associations

  • Fellow, American College of Tax Counsel
    • Secretary/Treasurer (2018-)
    • Regent (4th Circuit) (2017-18)
  • Fellow, Litigation Counsel of America
  • Fellow, Maryland Bar Foundation
  • Trustee, Baltimore Bar Foundation
  • MD State Bar Association: Taxation Section
    • Council (2001-14)
    • Chair (2008-09)
    • Chair-Elect (2007-08)
    • Secretary/ Treasurer (2006-07)
    • Tax Controversy Group, Founder
      • Chair (2004-08)
      • Advisor (2009-14)
  • American Bar Association, Section of Taxation
    • Civil and Criminal Tax Penalties Committee
      • Chair, (2019-)
      • Vice-Chair (2009-14, 2017-19)
      • Sub-Committee Chair - Important Criminal Developments (2004-08)
    • Appointments to the Tax Court Committee (2019-)
    • Nominating Committee (2011-14, 2018-19)
    • Public Fellowship Committee (2009-13)
    • Pro Bono Award Committee (2012-14)
    • Member, Serjeant’s Inn
    • Member, Rule Day Club
    • Member, Barrister’s Club
  • Member, U.S. Tax Court Inn of Court
  • Member, Women’s White Collar Defense Association
  • Member, Network 2000
    • Co-chair, Women of Excellence Luncheon (2013-14)
    • Member, Board of Directors (2014)
  • Member, Board of Directors, Maryland Volunteer Lawyer Service (2009-14)
    • Chair, Annual Benefit (2012-14)
  • 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 (2006-14)
  • Member, Advisory Board, Thomson West Tax (2007-14)
  • Member, Tax Advisory Board, Wolters Kluwer (2013-14)
  • Member, Advisory Board, CCH Journal of Tax Practice & Procedure (2011-14)
  • Instructor, Military Volunteer Income Tax Assistance (VITA) Program, Fort George G. Meade, Fort Meade, Maryland (2012-15, 2018)
  • Member, Advisory Board, Choice Jobs Program (2010-15)
  • Member, Advisory Board, Fannie Angelos Program for Academic Excellence (2014)
  • Sponsor, U.S. Naval Academy Sponsor Program

Upcoming Speaking Engagements

  • Panelist, Application of Authority in the Changing World of Deference, 67th Annual Taxation Conference, University of Texas School of Law, Austin, TX (December 5, 2019)

  • Panelist, Balancing Tax Planning, Advocacy, and Professional Ethics: The Rules that Every Tax Advisor Should Know, Tax Strategies for Corporate Acquisitions, Dispositions, Spin-Offs, Joint Ventures, Financings, Reorganizations & Restructurings 2019, Practicing Law Institute, Los Angeles, CA (December 6, 2019)
  • Panelist, Tax Fraud Red Flags, Financial Crimes Enforcement Conference, American Bar Association/American Bankers Association, Washington, D.C. (December 9 and 10, 2019)

  • Speaker, Criminal Tax Workshop, 36th Annual National Institute on Criminal Tax Fraud and 9th Annual National Institute on Tax Controversy, Las Vegas, NV (December 11, 2018)

  • Panelist, The Consequences of Conviction – The Sentencing Guidelines, Restitution, Forfeiture and Other Bad Things That Happen, 36th Annual National Institute on Criminal Tax Fraud and 9th Annual National Institute on Tax Controversy, Las Vegas, NV (December 12, 2019)

Presentations

  • Moderator, A Conversation with Nina Olson, former National Taxpayer Advocate, 2019 New England IRS Representation Conference, Uncasville, CT (November 22, 2019) 

  • Panelist, Criminal Aspects of IRS Collection Cases, 2019 New England IRS Representation Conference, Uncasville, CT (November 22, 2019)
  • Panelist, What You Really Need to Know if You are Taking on a Criminal Tax Case, 2019 Criminal Tax Update, Pennsylvania Association of Criminal Defense Lawyers, Philadelphia, PA (November 21, 2019) 

  • Speaker, Tax Controversies - IRS Practice Update, Sophisticated Tax Planning for Your Wealthy Clients, AICPA, Philadelphia, PA (November 18, 2019)
  • 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, International Enforcement - What’s Old, What’s New and What We Can Expect, 35th Annual UCLA Extension’s Tax Controversy Institute, Beverly Hills, CA (October 22, 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) 

  • Panelist, No Good Deed Goes Unpunished: Potential Liability of Executors and Beneficiaries for a Decedent's Tax Liabilities, Serjeant's Inn (October 2, 2019) 

  • Speaker, Preserving Confidentiality in Cross Border Investigations, 37th Annual Cambridge, England International Symposium on Economic Crime (September 3, 2019)

  • Panelist, Cooperation or Compulsion: The Emerging U.S. Experience With Voluntary and Involuntary Disclosures of Foreign Transactions, 37th Annual Cambridge, England International Symposium on Economic Crime (September 3, 2019)

  • Panelist, Ethical Pitfalls and How to Avoid Them When Representing Clients in IRS Collections and Audits, University of San Diego School of Law - RJS LAW Tax Controversy Institute 2019, San Diego, CA (July 19, 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, Are Your Secrets Safe? A Discussion of the Scope, Application and Protection of Legal Privileges in the U.S. and Abroad, ABA Taxation Section, May Meeting, Washington, D.C. (May 11, 2019)

  • Panelist, Collection-Based Tax Crimes, May Meeting, Section of Taxation, American Bar Association, Washington, DC (May 10, 2019)

  • Panelist, Parallel Proceedings, 3d Annual Lightfoot White Collar Institute, Birmingham, AL (May 8, 2019)

  • Speaker, Business or Pleasure? Navigating the Internal Revenue Code When Your Boat is a Business, Recreational Boating Committee of the Maritime Law Association of the United States, New York, NY (May 2, 2019)

  • Panelist, Tax Advice in the Age of the 24-Hour News Cycle, Webinar, ABA Taxation Section (April 24, 2019)

  • Speaker, What’s New in Tax Enforcement – Current Priorities of the IRS and DOJ Tax Division, The Wranglers Law Club, Baltimore, MD (April 18, 2019)

  • Co-Chair/Moderator, Identifying the Line Between Avoidance and Evasion: Global Criminal Tax Enforcement, 19th Annual U.S. and Europe Tax Practice Trends Conference, ABA, Paris, France (April 5, 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)

Past Presentations

2018, 2017


Publications

  • Pros and Cons of Voluntarily Disclosing Past Wrongs, Wendy Abkin, George Abney, and Caroline Ciraolo, Tax Executive Institute (February 2018)

  • 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 United States Strikes Again – The New Swiss Bank Program, Financier Worldwide (October, 2013)
  • 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)
  • 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)
  • 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)
  • Ask the Professionals (Various Tax-Related Topics), Baltimore Business Journal (2010 – present)
  • 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)
  • 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)

Contact

Email: CCiraolo@kflaw.com

Tel: 443-845-4898

DC Office
601 New Jersey Avenue, NW
Suite 620
Washington, DC 20001 

MD Office
300 E. Lombard Street
Suite 840
Baltimore, MD 21202

vCard


https://d3n8a8pro7vhmx.cloudfront.net/kflaw/pages/1313/attachments/original/1528732795/CDC_superlawyers_top_10.png?1528732795

undefined

 

 

 


News

December 11, 2019

Caroline D. Ciraolo Participated in the Criminal Tax Workshop at the 36th Annual National Institute on Criminal Tax Fraud / the 9th Annual National Institute on Tax Controversy in Las Vegas, NV


December 10, 2019

Caroline D. Ciraolo Participated in the Panel Entitled "Tax Fraud Red Flags" at the ABA/ABA Financial Crimes Enforcement Conference on December 9-10, 2019

View All >

Publications

February 05, 2018

Pros and Cons of Voluntarily Disclosing Past Wrongs


Education

  • 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)

Bar Admissions

  • 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, Federal Circuit
  • US Supreme Court

Faculty Positions

  • Adjunct Professor, Georgetown University Law Center (International Tax Controversies)
  • Adjunct Professor, University of Baltimore School of Law and Graduate Tax Program (Investigation, Prosecution and Defense of Tax Crimes)