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 tax tribunals, providing related tax advice, including advice on uncertain tax positions, financial reporting, claims for refund, amended returns, voluntary disclosures, and internal investigations, and representing individuals and institutions in criminal tax investigations and prosecutions.

During her tenure with the 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 statutes 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 Regent of the American College of Tax Counsel, a recipient of the ABA Section of Taxation’s Janet Spragens Pro Bono Award, and 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, Benchmark, Best Lawyers in America, Super Lawyers (Top 10 Attorneys in Maryland, and 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.  In January, 2017, Caroline was recognized by IRS Chief Counsel William Wilkens with the Chief Counsel Award, the highest honor that can be conferred by that office.

Caroline served as an Attorney Advisor for the Honorable Stanley J. Goldberg of the U.S. Tax Court from 1994 to 1996.


Government Experience

  • 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), Tax Division, U.S. Department of Justice, Washington, DC
  • Attorney Advisor, Honorable Stanley J. Goldberg, U.S. Tax Court (August 1994 – August 1996), Washington, DC

REPRESENTATIVE CIVIL MATTERS

  • In re Interstate Subpoena for Custodian of Records, Misc. Petition No. 29618M, Circuit Court for Montgomery County, MD (March 27, 2014) (successfully intervened in and obtained a protective order in response to a grand jury subpoena for a client’s records in the possession of an accountant)
  • United States v. Stahlnecker, Case No. 1:13-cv-01050-MJG, U.S. District Court for the District of Maryland (February 25, 2014) (successfully negotiated a settlement of a suit to reduce a federal tax lien to judgment, resulting in a substantial reduction of assessed trust fund recovery penalties).
  • Signature Flight Support Corporation v. Supervisor of Assessments for Anne Arundel County, Case No. 13-MI-AA-0579 (1-2), Maryland Tax Court (January 22, 2014) (successfully challenged the denial by the State Department of Assessment and Taxation and the Property Tax Assessment Appeals Board for Anne Arundel County (“PTAAB”) of an application for exemption from property tax on substantial improvements at the Thurgood Marshall Baltimore Washington International Airport, establishing that client was exempt as lessee of property owned by the State and used for a concession at a public airport)

 View Additional Representative Civil Matters


REPRESENTATIVE CRIMINAL MATTERS 

  • Represented individual investigated for filing false income tax returns resulting in a loss of more than $700,000. Negotiated a plea and 2014, persuaded the court to grant a downward variance, resulting in sentence of probation.
  • Represented individual investigated for filing false income tax returns.  Negotiated a misdemeanor plea to a single count of 26 U.S.C. 7207 and successfully argued for a probationary sentence.
  • Represented individual investigated for failing to file foreign bank account reports and filing false income tax returns resulting in a loss of more than $800,000.  Client charged with a single violation of 26 U.S.C. 7201 resulting in an advisory Guideline range of 24 to 30 months.  Persuaded court to grant downward variance, resulting in sentence of a year and day, with a recommendation for direct placement to a local residential reentry center (formerly referred to as community confinement or halfway house).

 

View Additional Representative Criminal Matters


Upcoming Speaking Engagements

  • Moderator and Speaker, "OVDP – End of an Era," May Meeting, Section of Taxation, American Bar Association, Atlanta, GA (October 6, 2018)

  • Speaker, “The New Wave Of Fraud Referrals – Fact Or Fiction," 34th Annual UCLA Extension’s Tax Controversy Institute, Beverly Hills, CA (October 23, 2018)

  • Speaker, “United States v Colliot: Defending Title 31 FBAR Penalties: Pre and Post Assessment, IRS and DOJ Policies and Strategy Post Colliot,” 14th Annual University of San Diego School of Law Procopio International Tax Institute, San Diego, CA (November 1, 2018)

  • Speaker, “It’s A Small World - The Use of Exchange of Information for Tax Enforcement,” 55th Annual Hawaii Tax Institute, Honolulu, Hawaii (November 6, 2018)

  • Speaker, "Update on Employment Tax Audits, Litigation, and Collections," 2018 Annual Meeting of the California Tax Bar & California Tax Policy Conference, San Jose, CA (November 9, 2018)

Awards and Recognitions

  • Recognized as a Top Tax Lawyer by Washingtonian (2017) 

  • Recognized as a Women in Tax Leader by International Tax Review (2017)
  • IRS Office of Chief Counsel Award (2017)

  • The Daily Record’s Leadership in Law (2015)

  • Chambers USA, Nationwide: Tax Fraud 

  • Best Lawyers in America - Litigation & Controversy – Tax; 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)

  • Maryland Super Lawyers (Tax) (2009 - 15); 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 in CNN Money Magazine – Money Hero (April 2013)

  • Featured on the cover of Maryland Super Lawyers Magazine (2013)

  • Benchmark: America's Leading Litigation Firms and Attorneys 

  • Baltimore SmartCEO Magazine's Legal Elite 

  • Martindale-Hubbell® Bar Register of Preeminent Women Lawyers™

  • Janet R. Spragens Pro Bono Award, ABA Section of Taxation 

  • The Daily Record's Top 100 Women in Maryland

  • The Daily Record’s Circle of Excellence (Women in Maryland)

  • Maryland Volunteer Lawyers Service Educator Award 

  • U.S. Tax Court Pro Bono Program, Maryland State Bar Association – Founder, Coordinator, and Volunteer 


Speaking Engagements

  • Panelist, “It’s Good to Know the Bad: Financial Crime and How to Counsel Clients,” Annual Meeting, Business Law Section, American Bar Association, Austin, TX (September 14, 2018)

  • Speaker, "Keynote Address; “Hot, Questionable, and Secret Money," 36th International Symposium on Economic Crime, Cambridge, England (September 4, 2018)

  • Speaker, "Unexplained Wealth in the US: The USA Flexes its Muscle," 36th International Symposium on Economic Crime, Cambridge, England (September 4, 2018)

  • Plenary Keynote Speaker, “Tax: The Good, the Bad, and the Ugly,” Accounting & Finance Show New York, Terrapinn, New York, NY (July 12, 2018)

  • Presenter, “Identifying and Addressing Conflicts of Interest and Ethical Issues in Today’s Tax Practices,” 42nd Annual Institute, American Institute on Federal Taxation, Hoover, AL (June 29, 2018)

  • Panelist, “Department of Justice Update,” 10th Annual Tax Controversy Forum, New York University, New York, NY (June 22, 2018)

  • Moderator, "May I Have My Money Back Now Please? The Legal Landscape Overseas And Strategies To Navigate International Asset Seizures", 10th Annual Tax Controversy Forum, New York University, New York, NY (June 22, 2018)

  • Panelist, “Answers Needed: Tax Research for Tax Problem Resolution Practitioners,” Spring Conference, American Society of Tax Problem Solvers, Atlanta, GA (June 8, 2018)

  • Panelist, "The Criminal Prosecution: Prosecution & Defense Strategies, the Plea, and Sentencing", Quinnipiac University 2nd Annual Criminal Tax Day, North Haven, CT (May 17, 2018) 
  • Panelist, "What's New In Criminal Tax?", Quinnipiac University 2nd Annual Criminal Tax Day, North Haven, CT (May 17, 2018)
  • Panelist, “Fundamentals of Tax Litigation: Choice of Forum and Appealing Decisions,” May Meeting, Section of Taxation, American Bar Association, Washington D.C. (May 12, 2018)
  • Panelist, “The Gathering Storm: Grappling with the Impact of Restitution Orders on Civil Tax Litigation,” May Meeting, Section of Taxation, American Bar Association, Washington, D.C. (May 11, 2018)
  • Panelist, “Collection of Title 31 International Penalties,” May Meeting, Section of Taxation, American Bar Association, Washington, D.C. (May 11, 2018)

  • Panelist, “Ethical Considerations for Government and Private Sector Tax Lawyers,” Government and Public Sector Lawyers Division and Taxation Section, American Bar Association, Webinar (April 26, 2018)

  • Panelist, “Fundamentals of Tax Litigation: Choice of Forum and Appealing Decisions,” Young Lawyers Tax Symposium, Section of Taxation, American Bar Association and Federal Bar Association, Washington D.C. (April 13, 2018)

  • Presenter, “Impact of Global Tax Enforcement,” Graduate Tax Scholars, Georgetown University Law Center, Washington, D.C. (March 29, 2018)

  • Panelist, “Exchange of Tax Information Around the World,” 68th Midyear Conference, Tax Executive Institute, Washington, D.C. (March 28, 2018)

  • Moderator, "Tools Of The Trade - A Review Of The Government's Arsenal In Criminal Tax Investigations", 2018 FBA Tax Law Conference, Washington, D.C. (March 9, 2018)

  • Panelist, "Balancing Privileges And Burdens Of Proof In Civil Trials Involving International Taxpayers, Crypto-Currency And Marijuana Businesses", 2018 FBA Tax Law Conference, Washington, D.C. (March 9, 2018)

  • Presenter, "Taking On A Criminal Tax Case? Don’t Leave Home Without These Critical Practice Tips", 32nd Annual National Institute on White Collar Crime, San Diego, CA (February 28, 2018)

  • Presenter, "The Impact Of Global Tax Enforcement", 2018 E.L. Wiegand Lecture, San Francisco, CA (February 16, 2018)

  • Presenter, "The New Wave Of Fraud Referrals – IRS Collections", 2018 ABA Taxation Section Midyear Meeting, San Diego, CA (February 10, 2018)
  • Presenter, "Evolving Constraints On Tax Administration At The IRS", 2018 ABA Taxation Section Midyear Meeting, San Diego, CA (February 9, 2018)
  • Panelist, "Is There A Tipping Point?", Women's Leadership Forum, London, England (January 23, 2018)
  • Volunteer, IRS Military Volunteer Income Tax Assistance Adopt-A-Base Program, Fort Meade, MD (January 8, 2018)

  • Speaker, "Penalties Above 20%: What Are They, When Are They Applied, And How Do You Defend?", 65th Annual Taxation Conference, University of Texas School of Law, Austin, TX (December 13, 2017)

  • Moderator, Criminal Tax Workshop, 34th Annual National Institute on Criminal Tax Fraud and 7th Annual National Institute on Tax Controversy, Las Vegas, NV (December 6, 2017)

  • Speaker, "AML And Tax – What Every AML Officer Should Know About The New And Emerging Tax Issues", 2017 American Bankers Association and the American Bar Association Financial Crimes Enforcement Conference, National Harbor, MD (December 4, 2017)

  • Panelist, "Cross Border Individual Matters", 30th Annual Institute on Current Issues in International Taxation, Georgetown Law School, Washington, D.C. (December 1, 2017)

  • Presenter, "Global Tax Enforcement: Compliance & Risk Mitigation", Bahamas Financial Services Board, Nassau, Bahamas (November 29, 2017)

  • Speaker, "Waking Up The Dead: Reopening Those Tax Assessments You Thought Were Final", 2017 New England IRS Representation Conference, Mashantucket, CT (November 17, 2017)

  • Speaker, "The IRS And DOJ Continue To Prioritize Employment Tax Enforcement - Are You And Your Clients Prepared?", 2017 Annual Meeting of the California Tax Bar & California Tax Policy Conference, Carlsbad, CA (November 2, 2017)

  • Moderator, "Continuing Enforcement And Disclosure Issues Regarding Foreign Assets", 5th Annual ABA International Tax Enforcement And Controversy Conference, Washington, D.C. (October 27, 2017)

  • Speaker, "Voluntary Disclosures - Righting Past Wrongs", Tax Executives Institute 72nd Annual Conference, Toronto, Canada (October 25, 2017)

  • Speaker, “From The Experts: IRS Representation Tools, Techniques, And Defensive Strategies – Civil & Criminal Tax Update", 76th Institute on Federal Taxation, New York University, New York, New York (October 22, 2017) - download brochure

  • Speaker, "Trends In Tax Transparency And Enforcement", Association of Certified Financial Crime Specialists (ACFCS) 2017 Financial Crime Conference, Boston, MA (October 17, 2017)

  • Speaker, "Developments In International Tax Enforcement", D.C. Bar Tax Audits and Litigation Committee, Washington, D.C. (October 11, 2017)

  • Speaker, "Tax Defense", 13th Annual East Coast White Collar Crime Conference, Washington, D.C. (September 14, 2017)
  • Speaker, "U.S. International Tax Enforcement And Compliance", 35th International Symposium on Economic Crime, Cambridge, England (September 5, 2017)

  • Speaker, "Keynote Address", 35th International Symposium on Economic Crime, Cambridge, England (September 4, 2017)
  • Speaker, "Examination Do's and Dont's", National Association of Tax Professionals, Washington, D.C. (August 10, 2017)

  • Speaker, "Conflicts of Interest", National Association of Tax Professionals, Washington, D.C. (August 9, 2017)

  • Speaker, "IRS Office of Chief Counsel Lecture Series", Washington, D.C. (June 29, 2017)

  • Panelist, "A Perspective on IRS Virtual Currency Enforcement Action", Blockchain, Accounting, Audit & Tax Conference, Microsoft Technology Center, New York, NY (June 22, 2017)

  • Panelist, "Tax Compliance and Enforcement Update – Department of Justice", NYU 9th Annual Tax Controversy Forum, New York, NY (June 16, 2017)

  • Panelist, "International Exchange of Information and Evidence Gathering", NYU 9th Annual Tax Controversy Forum, New York, NY (June 15, 2017)

  • Panelist, "Tax Enforcement Update: Significant Issues", Texas Federal Tax Institute, San Antonio, TX (June 14, 2017)

  • Speaker, "Coming Attractions in Tax Controversies", 2017 Spring Conference, American Society of Tax Problem Solvers, San Antonio, TX (June 10, 2017)

  • Panelist, “IRS Employment Tax Audits – Part II", May Meeting, ABA Section of Taxation, Washington, DC (May 12, 2017)
  • Luncheon Speaker, "Audits & Appeals Seminar (Insights and Skills for Federal Tax Controversy Success)", Tax Executives Institute, Chicago, IL (May 8, 2017)
  • Panelist, "Offshore Tax Compliance Issues (from a Tax Controversy Perspective)", Advanced Tax Procedure Seminar, Tax Section of the Florida Bar, West Palm Beach, FL (May 5, 2017)
  • Panelist, "So This Is Privileged… Right?", Advanced Tax Procedure Seminar, Tax Section of the Florida Bar, West Palm Beach, FL (May 5, 2017)
  • Panelist, “Recent Trends In Information-Gathering And Enforcement By The IRS, ICE, FinCEN, and DOJ,” 17th Annual Anti-Money Laundering Compliance Conference, Florida International Bankers Association (FIBA), Miami, FL (March 8, 2017)
  • Panelist, “The Art of Storytelling as told by Women Leaders in Government,” 31st Annual National Institute on White Collar Crime, Miami, FL (March 9, 2017)
  • Speaker, "Keynote Address", USC Gould School of Law 2017 Tax Institute, Los Angeles, CA (January 24, 2017)

Professional Associations

  • Fellow and Regent (4th Circuit), American College of Tax Counsel
  • 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), and Advisor (2009 - 14)
  • American Bar Association, Section of Taxation - Civil and Criminal Tax Penalties Committee [Vice-Chair (2009 – 14, 17 - ); Sub-Committee Chair - Important Criminal Developments (2004 - 08)]; Nominating Committee (2011 - 14); Public Fellowship Committee (2009 - 13); Pro Bono Award Committee (2012 – 14)
  • Fellow, Maryland Bar Foundation
  • Member, Board of Directors, Maryland Volunteer Lawyer Service (2009 - 14)
    • Chair, Annual Benefit (2012 – 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)
  • Member, Serjeant’s Inn
  • Member, Rule Day Club
  • Member, Barrister’s Club
  • Member, Network 2000
    • Co-chair, Women of Excellence Luncheon (2013 – 14)
    • Member, Board of Directors (2014)
  • Instructor, Military Volunteer Income Tax Assistance (VITA) Program, Fort George G. Meade, Fort Meade, Maryland (2012 – 15)
  • 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 (2013 - present)

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

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News

October 17, 2018

Caroline Ciraolo Profiled By Maryland Super Lawyers Magazine


October 17, 2018

K&F Provides Insights At ABA Fall Tax Meeting In Atlanta

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, University of Baltimore School of Law and Graduate Tax Program (Investigation, Prosecution and Defense of Tax Crimes) (Fall, 2018)

Adjunct Professor, Georgetown University Law Center (International Tax Controversies) (Spring, 2019)