James N. Mastracchio
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Jim is widely recognized as one of the foremost advisers to the global tax community with regard to civil and criminal tax enforcement matters. He represents clients in all phases of federal civil tax controversies. Jim is one of the few lawyers in the country who has served as lead counsel on international criminal tax cases. In that role, he has defended publicly traded companies, boards of directors, and senior management facing criminal investigations and prosecutions for alleged tax violations.
Key Matters
Some of the experience represented below may have been handled at a previous firm.
Significant Active Federal Court Representations
- Filed US Supreme Court certiorari for a real estate development company regarding excessive valuation penalties
- Representing an estate in the 2ndCircuit Court of Appeals challenging the validity of Treasury Regulation 1010.820(g)(1)
- Representing a taxpayer before the 11thCircuit Court of Appeals regarding proper burden of production standard under IRC Section 7491
- Asserting claim of right tax benefits in US Tax Court for a mortgage company
- Defending a taxpayer facing civil fraud penalties in US Tax Court
- Representing four taxpayers facing whipsaw tax and civil fraud penalties in US Tax Court
Successful Engagements
- Successfully counseled clients resolve examinations of syndicated partnership conservation easement transactions
- Represented a cooperative in Internal Revenue Service (IRS) Appeals regarding proper interpretation of Treasury Regulations and successfully settled the matter
- Counseled clients facing investigations into offshore holdings and structured products and resolved those investigations favorably for those clients
- Represented clients before the New York State Attorney General’s Taxpayer Protection Bureau regarding New York State’s False Claims Act
- Represented multi-national clients before IRS Appeals in conjunction with the U.S. Competent Authority
- Successfully defended an international company facing criminal tax charges for insurance-related tax products
- Served as lead counsel in the criminal tax prosecution of a financial institution and its subsidiaries located in the Cayman Islands. The investigation resulted in declination letters being issued to the publicly traded company and financial institution with modest penalties being paid by two small subsidiaries through a cooperative plea agreement.
- Advised clients regarding resolution of conservation easement disputes with the IRS
- Successfully defended a civil and criminal tax dispute involving the question of the proper definition of loss of income insurance and allowable premium deductions
- Represented a client in a tax dispute regarding timing and amount of assets placed in service
- Defended against allegations by the IRS that the client was subject to a section 481 change in accounting method adjustment
- Achieved a full concession at IRS Appeals of an alleged tax shelter promotor penalty
- Defended a client in a tax controversy regarding the proper valuation of exploratory oil property contributed to a municipal government
- Acted as an independent examiner in the U.S. Department of Justice’s Swiss Bank Program
- Counseled a client in a controversy related to the inability of the IRS to impose penalties without prior written approval pursuant to IRC Section 6751
- Defended a client in a tax dispute regarding an alleged tax and 40% valuation penalty, which was dropped after a successful argument that the statute of limitations for assessment had expired
- Secured the abatement of millions of dollars in penalties for a client in a dispute over the proper classification of independent contractors and employees
- Defended a client in a controversy related to the proper tax treatment of a construction contract settlement
- Represented more than 850 taxpayers who participated in the IRS Offshore Voluntary Disclosure Program
- Defended taxpayers facing penalties for failing to timely file Form 5471 and Form 8938
- Successfully raised Fifth Amendment assertions in an offshore civil penalty tax dispute
- Resolved a Freedom of Information Act dispute, gaining access to needed documentation from the IRS, which resulted in a case concession by the government
- Defended a client facing income and penalties as a result of deficiencies in IRS Tax Equity and Fiscal Responsibility Act (TEFRA) proceedings