Overview
Frank J. Jackson focuses his practice on federal and state tax controversies at every stage, including tax audits, administrative appeals and litigation. Over the last two decades, Frank has successfully represented domestic and multinational businesses, nonprofits and high-net-worth individuals and estates in disputes involving a wide variety of sophisticated tax matters.
At the examination and appeals stages of tax controversies, Frank achieves client goals through his substantive and procedural knowledge, strong communication and negotiation skills and innovative strategies. When litigation cannot be avoided or is in his client’s best interest, he provides effective representation in hearings and trials before the US Tax Court and US district courts. In cases where tax liabilities have been assessed but not paid, Frank represents clients before the Internal Revenue Services’ (IRS) Collection Division, including in the negotiation of installment agreements, offers in compromise and in resolving lien priority and levy disputes.
Frank has firsthand understanding of the priorities and processes of tax authorities. Early in his career, he served as a trial lawyer and National Tax Shelter Project lawyer for the IRS. In this capacity, he represented the agency in suits before the Tax Court and provided legal advice to revenue agents and officers.
Additionally, Frank handles sensitive tax matters involving fraud allegations and has extensive experience helping clients avoid penalties and criminal charges. To help US taxpayers ensure compliance with federal and state tax laws, he offers counsel on voluntary disclosure initiatives, including previously undisclosed foreign financial accounts, and regularly helps clients correct compliance errors.
Frank is also an avid writer and public speaker on tax law topics.
Results
- Successfully resolved US Tax Court litigation on behalf of a corporate officer and closely-held corporation, involving the deductibility of certain business expenses. While the matter was initially a criminal referral by the IRS Criminal Investigation, our team resolved the case civilly without the imposition of fraud penalties.
- Successfully obtained retroactive reinstatement of a global not-for-profit organization’s federal tax-exempt status as well as abatement of all related penalties, avoiding more than $20 million in tax, penalties and interest*
- Successfully negotiated the resolution of a New York sales tax examination on behalf of a multinational company, its subsidiary and executives as purported responsible persons*
- Advised a Fortune 100 multinational corporation in restructuring its global tax department to optimize compliance with domestic and global reporting requirements and maintain confidentiality for sensitive, privileged materials*
- Obtained full concession from the IRS in a Tax Court matter affirming a taxpayer’s position that $50 million in proceeds from litigation funding was properly characterized as long-term capital gain*
- Successfully quashed a series of summonses served on US financial institutions pursuant to the United States-Russian tax treaty and at the request of the Russian Federation*
- Represented and lead trial counsel in a Tax Court case involving a large multinational hedge fund advisory firm to determine whether the fund was “engaged in a US trade or business” and was effectively connected income as result of its investment activities and whether the fund was subject to withholding under Internal Revenue Code (IRC) Section 1446*
- Represented a multinational corporation during an IRS examination and administrative appeal with respect to the characterization and valuation of intangible assets under IRC Section 936 as a result of a corporate reorganization and deemed liquidation of the taxpayer into its foreign parent*
- Represented a large estate in a complex Tax Court case involving the valuation of an estate comprised of original works of art and the calculation of the appropriate blockage discount*
- Represented a large national accounting firm in a federal grand jury investigation and promoter penalty audit relating to the development, marketing and reporting of tax shelter transactions; assisted in negotiating a deferred prosecution agreement and an IRS closing agreement to resolve both; and assisted in the creation of the accounting firm’s ongoing compliance and ethics plan*
- Represented a for-profit college and negotiated favorable settlement with the IRS regarding the disallowance of the client’s claimed research and development credits, change in income tax accounting method and treatment of deferred income*
- Favorably resolved promoter penalty audits, transferee liability assessments and criminal tax investigations for a corporate client and its more than 60 subsidiaries that had engaged in (and promoted) “Midco” transactions whereby gain on the sale of assets was sheltered by the sale of loss assets contributed to a corporation*
- Represented employers in worker classification issues and participation in the IRS Voluntary Classification Settlement Program*
- Obtained favorable settlement in a Tax Court matter involving transferee liability*
- Represented the CEO of a large retailer in their dispute with the IRS regarding the disallowance of passive activity losses and the validity of a variable prepaid forward contract*
- Represented a vineyard in an IRS examination of a client’s use of a split-dollar life insurance arrangement and participation in an employer welfare benefit plan*
- Successfully litigated complex estate deficiency in the Tax Court matter involving the disallowance of certain estate deductions and administrative expenses*
*Matter handled prior to joining McDermott.
Recognitions
- Legal 500 US, Recommended, 2024
- IRS Division Counsel Cube Award, 2004
Community
- American College of Tax Counsel, fellow
- ABA Section of Taxation, Committee on Tax Practice Management, past chair
- ABA Section of Taxation, Committee on Diversity in the Profession, member
Credentials
Education
New York University School of Law, LLM, Taxation, 2000
New England Law | Boston, JD, cum laude, 1997
University of Tennessee, BA, 1992
Courts/Agencies
US District Court for the District of Massachusetts
US Tax Court
Admissions
Massachusetts
New York
Tennessee