Practice Focus

Brad assists private foundations and public charities with navigating complex tax regulations and procedures, including receipt and disposition of complex charitable gifts and participation in innovative forms of impactful philanthropy. He also advises on governance matters, guiding charities and other nonprofits through formation, reorganizations, mergers, affiliations, and dissolutions.

Additionally, Brad advises private clients on securing their long-term goals related to preserving and protecting their wealth and executing their philanthropic endeavors. He counsels families on structured charitable giving, estate planning and lifetime gifting strategies. Brad was recognized as a Notable Practitioner assisting US and international high net worth families with philanthropy and trusts and estates planning in Chamber’s High Net Worth guide. He is also a Fellow and Regent of the American College of Trust and Estate Counsel.

Brad has 20 years of experience in private practice with national firms and also previously worked as a tax law specialist with the Exempt Organizations Division of the IRS in Washington, D.C. Before his legal career, Brad obtained advanced degrees in English language and literature and taught medieval literature at universities in the United Kingdom, Japan, and the United States.

Brad is also a Senior Vice President and Chair of the Audit Committee at Hemenway Trust Company, a New Hampshire based private fiduciary firm.

Representative Experience

• Advised higher education institution on planned and structured giving programs, including overhaul of gift acceptance policies and procedures, development of charitable gift annuity and charitable remainder trust programs, and onboarding of complex gifts.
• Negotiated complex integration, including extensive coordination with local and state governmental organizations, of cultural nonprofit with larger charity to ensure the financial stability and enhance the programmatic offerings for both organizations.
• Procured abatement from IRS of $10M in tax assessments and penalties against private foundation.
• Assisted university in negotiating, accepting and managing complex charitable gifts, including charitable remainder trusts, gift annuities, and gifts of interests in real estate and closely-held businesses.
• Advised on administration of endowment and restricted funds, including appropriations, terminations, and cy pres or deviation actions.
• Provided tax analysis to university establishing commercialization fund to help transition university research to the marketplace.
• Represented educational organizations in spin-off of program into separate non-profit and subsequent merger.
• Advised tax-exempt organizations on issues pertaining to partnerships with for-profit entities and unrelated business income tax, including the tax on parking and transportation benefits.
• Helped establish first pay-for-success bond to include donor-advised funds as investors
• Developed donor-advised fund program for community foundation
• Negotiated first non-judicial settlement agreement involving charitable organizations and the Office of the Attorney General of the Commonwealth of Massachusetts
• Negotiated terms of endowment fund with City of Boston for maintenance of city park
• Assisted family with highly appreciated post-IPO stock dispose of stock in tax efficient manner, including combination of gifts to charitable remainder unitrusts, private foundations, and public charities