Caroline D. Ciraolo was appointed Principal Deputy Assistant Attorney General and Deputy Assistant Attorney General of Policy & Planning of the Tax Division on January 12, 2015. On October 5, 2015, Ms. Ciraolo assumed the role of Deputy Assistant Attorney General for Criminal Matters. In her role as Principal Deputy Assistant Attorney General, Ms. Ciraolo is the senior management official in charge of the Tax Division.
Prior to her appointment in the Tax Division, Ms. Ciraolo was Chair of the Tax Controversy and Litigation practice group at Rosenberg Martin Greenberg, LLP, in Baltimore, MD, where she represented individuals and businesses in all phases of state and federal civil tax controversies and criminal tax investigations and prosecutions. Ms. Ciraolo has appeared before the IRS, the Comptroller of Maryland and the D.C. Office of Tax and Revenue, the Maryland Tax Court, the United States Tax Court, United States District Courts, the Maryland circuit and appellate courts and the United States Court of Appeals for the Fourth Circuit.
Ms. Ciraolo began her career as an Attorney Advisor for the Honorable Stanley J. Goldberg of the United States Tax Court, and worked for Martin, Junghans, Snyder & Bernstein, PA (1996-1998), and Martin, Snyder & Bernstein, PA (1998-2003), before joining Rosenberg Martin Greenberg, LLP.
Ms. Ciraolo received her B.S. in Finance (with honors) (cum laude) from the College of New Jersey, her J.D. (with honors) from the University of Maryland School of Law, and her LL.M. in taxation from the University of Baltimore School of Law. She is a member of the American Bar Association’s Section of Taxation, was a Fellow and Regent of the American College of Tax Counsel, and former Chair of the Maryland State Bar Association Taxation Section. Ms. Ciraolo has written and lectured extensively on a wide variety of civil tax controversy and criminal tax issues.
Ms. Ciraolo is a recipient of the ABA Section of Taxation’s Janet Spragens Pro Bono Award, was honored as Educator of the Year in 2008 for her work training volunteers for the Maryland Volunteer Lawyers Service low income taxpayer clinic, and since 2012 she has served as an instructor with the IRS Military Volunteer Income Tax Assistance (VITA) Program, at Ft. George G. Meade in Maryland.