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Lawyer Profile

Image of Caroline D. Ciraolo

Caroline D. Ciraolo

Kostelanetz & Fink, LLP
  • Recognized Since:
    2011
  • Recognized in:
    Litigation and Controversy - Tax
    Tax Law
  • Law School:
    University of Maryland
  • Website:
    http://www.kflaw.com
  • E-mail:
    cciraolo@kflaw.com
  • Location:
    601 New Jersey Avenue, NW, Suite 260
    Washington, DC 20001

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. accountholders, 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.  

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  • Lawyer Bio
  • Client Comments
  • Firm Details

Lawyer Bio

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. accountholders, 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.  

  • Education
  • Bar & Court Admissions
  • Affiliations
  • Award List
  • Clerkships
  • Lawyer of the Year Badge

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
 

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

Affiliations:

  • ABA, Section of Taxation - Vice Chair, Civil and Criminal Tax Penalties Commtitee
  • American College of Tax Counsel - Regent
  • Baltimore Bar Foundation - Trustee
  • Barrister's Club - Member
  • CCH Journal of Tax Practice & Procedure - Member, Advisory Board
  • Choice Jobs Program - Member, Advisory Board
  • Fannie Angelos Program for Academic Excellence - Member, Advisory Board
  • Federal Bar Association (Maryland Chapter) - Member, Board of Directors
  • Litigation Council of America - Fellow
  • Maryland Bar Foundation - Fellow
  • Maryland State Bar Association and Maryland Association of CPAs - Member, Advanced Tax Institute
  • Maryland Volunteer Lawyers Service - Member, Board of Directors
  • Military Volunteer Income Tax Assistance (VITA) Program - Instructor, Fort George G. Meade, Fort Meade, MD
  • Military Volunteer Income Tax Assistance Program - Instructor
  • MSBA, Taxation Section - Former Chair (2008-2009)
  • Network 2000 - Member
  • Rule Day Club - Member
  • Serjeant's Inn - Member
  • Thomson West Tax - Member, Board of Directors
  • U.S. Naval Academy Sponsor Program - Sponsor
  • U.S. Tax Court Inn of Court - Member
  • Wolters Kluwer - Member, Tax Advisory Board
  • Women's White Collar Defense Organization - Member

Named "Lawyer of the Year" by Best Lawyers for:

  • Litigation and Controversy - Tax, Baltimore (2012)
 

Recognized in The Best Lawyers in America 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 (2011 - 2014)
  • DC Super Lawyers (Tax) (2019)
  • Featured in CNN Money Magazine -- 2013 Money Hero (April 2013)
  • Featured on cover of Maryland Super Lawyers Magazine (2013)
  • 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™
  • Maryland Super Lawyers (Tax) (2009 - 14); Top 10 Attorneys in Maryland (2013 - 14); Top 25 Women Attorneys in Maryland (2009 - 11); Top 50 Women Attorneys in Maryland (2012 - 14); Top 100 Attorneys in Maryland (2010 - 14)
  • Maryland Volunteer Lawyers Service Educator Award (2008)
  • Maryland Volunteer Lawyers Service Educator Award (2008)
  • Recognized as a Top Tax Lawyer by Washingtonian (2017, 2018) 
  • Recognized as a Women in Tax Leader by International Tax Review (2017, 2018)
  • The Daily Record’s Circle of Excellence (Women in Maryland) (2014)
  • The Daily Record's Top 100 Women in Maryland (2010, 2012)
  • US Tax Court Pro Bono Program, Maryland State Bar Association – Founder (2008/2009), Coordinator (2008-10), Volunteer (2008-14)

Federal Clerkships:

  • United States Tax Court
 

Lawyer Client Comments

Firm Details

Image for Kostelanetz & Fink, LLP
Kostelanetz & Fink, LLP
http://www.kflaw.com
 
Headquarters
Seven World Trade Center, 34th Floor
250 Greenwich Street
New York, NY 10007
(212) 808.8100
2 Office Locations
in 1 Country

United States

United States

District of Columbia

District of Columbia

Washington, DC

601 New Jersey Avenue, NW, Suite 260

Washington, DC 20001

United States

(202) 875.8000

Get Directions

 
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