James N. Mastracchio is a member in Caplin & Drysdale’s Washington, D.C. office.
Mr. Mastracchio represents taxpayers in civil and criminal tax matters and white collar defense. He has expertise in handling voluntary disclosures, including advising clients through the IRS Voluntary Disclosure process where off-shore bank and investment accounts are a concern. He has extensive experience handling administrative cases within the Internal Revenue Service and in state administrative proceedings, including individual, partnership, and corporate examinations, administrative appeals, collection activity, penalties, injunctions, tax shelters, and the defense of tax practitioner sanctions. Recent representations have included section 6700 penalty investigations, listed transactions, taxpayer transferee liability cases, TEFRA procedural disputes, and various state sales tax and excise tax issues. In addition to handling responsible person penalty cases, he routinely advises U.S. and foreign financial institutions on informational reporting and withholding requirements. Mr. Mastracchio has litigated in U.S. Tax Court, the United States Court of Federal Claims, and U.S. District Court.
Mr. Mastracchio’s experience defending criminal investigations initiated by the Internal Revenue Service have included tax fraud and evasion, money laundering, currency reporting cases and other related federal prosecutions. In addition to Internal Revenue cases, he has represented health care providers, financial institutions and medical device companies under allegations of various Federal regulatory violations, mail and wire fraud, obstruction of justice, and other related criminal charges. In connection with allegations of corporate wrongdoing, Mr. Mastracchio has conducted numerous internal investigations and advises senior management and litigation committees on appropriate courses of action.
Prior to his law career, Mr. Mastracchio was a Certified Pubic Accountant with a national firm focusing on compliance issues. As a result of his in-depth experience in the accounting field, he is often involved in complex civil litigation cases involving accounting practice and procedural issues, allegations of accounting malpractice, and defending matters before the IRS Office of Professional Responsibility.
Mr. Mastracchio is currently the Chair of the Monetary Penalties and Forfeitures Subcommittee of the American Bar Association’s Civil and Criminal Tax Penalties Section. He is a Committee Member of the New York State Bar Association’s Tax Compliance, Practice and Procedure Committee. Mr. Mastracchio is a frequent panelist for professional organizations on various topics, including, electronic discovery, attorney-client and work-product privileges, Bank Secrecy Act and related regulatory reporting, FASB FIN 48 disclosure and Internal Revenue Service practice and procedure.