Our approach to tax is simple: translate an arcane tax code into plain English—decode its artifacts and incentives—so that you can make intelligent decisions and achieve your business, personal, and social goals. We help structure mergers and acquisitions, spin-offs, joint ventures, and financings for tax efficiency and minimized risk. We counsel you in identifying risks and opportunities within the complex interplay of tax laws, and explain these in terms that help you balance risk and cost. We zealously represent individual and business clients in audits, appeals, and litigation with the Internal Revenue Service, and with state and local tax authorities. We work with public companies, start-ups and entrepreneurs, family businesses, individual taxpayers, private equity and venture capital funds, family offices and private investors, expatriate employees and expatriate executives, foreign nationals working in the United States, foreign subsidiaries, non-U.S. businesses, private foundations and donor-advised funds, and public charities.

From convolution to solution. From roadblocks to starting blocks.

We offer practical solutions to both the daunting challenges and the everyday snags that arise throughout the business cycle. Using an interdisciplinary, strategic approach, we’ll evaluate your unique tax situation, policy aims, and goals; we then offer innovative and practical solutions. We advise taxpayers on how to execute operations in the most tax-efficient manner, and we advocate on your behalf with tax authorities. Our team employs its extensive experience and deep expertise to deliver results consistent with your personal, business, and financial goals.


Our firm provides structuring, counseling, and advocacy in all traditional areas:

Strategic Events: Mergers, Acquisitions, Joint Ventures, and Similar Deals

  • Deal structuring and tax planning
  • Tax opinions and due diligence
  • 1031 like-kind exchanges

Advice for Investment Entities

  • Private equity
  • Family partnerships
  • Real estate ventures

State Tax Planning and Advice

  • Nexus
  • Residency
  • Apportionment

Financially Challenged Entities

  • Preservation of tax benefits in workouts
  • Avoiding “cancellation of debt” income
  • Risk minimization for individuals or entities

Business Operations

  • Deferred compensation
  • Retirement plans
  • Payroll and tax reporting issues

We maintain an especially deep expertise in three boutique areas: international taxation, tax-exempt organizations, and business aviation.

Tax-exempt organizations

  • Structuring and securing tax-exempt recognition
  • Private foundations
  • Public charities
  • Joint ventures with taxable entities
  • Organizations operating outside the U.S.
  • UBIT Analysis
  • Political activities and lobbying.

International Tax Planning

  • Outbound:
    • Foreign tax credits
    • Deferral of U.S. tax on low-taxed foreign source income
    • Effective use of tax treaties
    • Tax efficient repatriation of earnings
    • U.S. tax support for non-U.S. operations of domestic clients
    • Federal export incentives
  • Inbound:
    • Tax treaty benefits
    • Permanent establishment issues
    • Cross- border withholding taxes
    • Earnings stripping
    • State income taxation
    • U.S. estate taxation

Business Aviation

  • Full deduction for costs and expenses
  • Taxability of employees and other passengers
  • Sales, use, and excise taxes
  • Deferral of gain in like-kind exchanges


Tax-Exempt/Taxable Joint Venture

We structured a U.S. charitable foundation’s affiliation with a for-profit enterprise based in Chile. We represented the U.S.-based non-profit, which promotes education, economic development, and environmental conservation in Chile through educational initiatives, teaching English and encouraging environmental awareness in schools and communities—conserving ecologically fragile areas and facilitating local community involvement. The Chilean for-profit partner is an eco-tourism and conservation operation, which owns ecologically sensitive properties and is developing a carbon sequestration credit and eco-brokerage as additional revenue sources.

National Advocacy Organization

For a multi-state educational reform advocacy group, we organized the nonprofit organization, obtained qualification under IRC §501(c)(3), and structured its governance. Compliance with federal and state lobbying rules, qualifications to do business, and compliance with applicable state charitable solicitation laws were achieved. We trained staff in lobbying and governmental affairs requirements. We also created and provided similar services for an IRC §501(c)(4) organization to conduct broader lobbying activities.

Non-Profit Reorganization

We helped a well-known public broadcasting company reorganize, enhancing its endowment function and allowing its new subsidiaries to qualify for additional tax benefits. We addressed fundraising, structuring, and UBIT issues.

Million Dollar Tax Refund

Our client did business in one state but lived in another. When he sold part of his business, his CPA advised him to pay tax on his gains in the state where he did business. Later, the tax authority in his residency state audited him and demanded tax on the same income. We reviewed and concluded that the CPA had made an error, but both states took the position that the tax was due to them. We advocated for the client in both states, and were successful in obtaining a large refund.

“No Change” on Hobby Loss Audit

Our client, an inventor, hired engineers and incurred other expenses for several years, but has had no taxable income as his products are not yet to market. IRS sought to deny the salaries and other expenses, alleging the inventor is not “engaged in business for profit.” On second-level appeal, we were successful in obtaining a “no change” determination and his tax returns were accepted as filed.

Case Studies

Case Study

A Win for Those in Need

Timothy S. Hollister represented Rainbow Housing Corporation and its affiliate Gilead Community Services, subsidiaries of mental health services providers Connecticut Institute for the Blind and Oak Hill, in a tax exemption case in the Connecticut Superior…

Case Study

Hinckley Allen Guides Major Urban Mixed-Use Redevelopment: Arsenal Yards

Hinckley Allen provided strategic counsel to Boylston Properties and The Wilder Companies, who recently secured the equity funding and construction loan necessary to begin construction of New England’s premier urban mixed-use redevelopment project. Arsen…

See all Case Studies

News & Insight

Firm News

Hinckley Allen Celebrates 11 Years a "Best Law Firm"

November 5, 2020

U.S. News & World Report and Best Lawyers have recognized Hinckley Allen for the eleventh consecutive year as a Best Law Firm. Hinckley Allen has been ranked nationally in five practice areas and regionally in 58 practice areas.Firms included in the …

Firm News

Hinckley Allen Celebrates 10 Years a “Best Law Firm”

November 1, 2019

U.S. News & World Report and Best Lawyers have recognized Hinckley Allen for the tenth consecutive year as a Best Law Firm. Hinckley Allen has been ranked nationally in five practice areas and regionally in 53 practice areas.Firms included in the 2020 …

See all Firm News

Tax Savings Through the Massachusetts SALT Cap Workaround

March 23, 2022

The Massachusetts Department of Revenue has provided guidance on its workaround to the federal income tax system’s $10,000 limit on deductions for state and local taxes for individuals (the “SALT Cap”). On March 18, 2022, it released Technical Inform…


2021 Individual Tax Extension Deadline

April 7, 2021

Last month, the Internal Revenue Service (IRS) announced that the Federal income tax filing and payment due date for individuals will be automatically extended until May 17, 2021.Unlike last year, the automatic Federal tax filing extension only applies to …

See all Publications