Sullivan
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We represent numerous high net worth individuals (HNWI) and family offices in a wide variety of areas.

Our tax strategies help HNWI reduce the impact of federal and state income, estate, and gift taxes. This includes advising on how to reduce or limit the impact of taxes on such appreciating family assets as real estate and closely held businesses and financial holdings, and developing the most effective structures to pass more of the increased value to younger family members. We also can help plan for the use of life insurance to increase estate liquidity upon death while avoiding tax on the insurance proceeds, and have developed software to analyze the optimum disposition of IRAs and other tax-qualified assets. Our state tax experts regularly assist clients with domicile planning and controversies relating to Massachusetts residency, as well as all manner of state tax planning that can affect individuals and businesses. Finally, and when necessary, we represent clients in connection with Internal Revenue Service and state audits.

We regularly advise on the tax consequences of investments in pass-through entities such as Subchapter S corporations, partnerships, and LLCs and help individuals to maximize the tax benefit of available deductions while minimizing the tax costs associated with various forms of income.

For clients with charitable objectives, we can help make the most of the tax benefits associated with charitable giving through a variety of strategies for charitable gift programs.

Family offices often present particularly unique challenges from clients who know just what they want but are often unsure of how to accomplish their goal. Years of experience supporting family offices has produced a talented team of advisors within our firm and in a wide variety of disciplines including corporate, real estate, securities, tax, employment, and benefits.

Representative Client Work

  • Represented a family office in multiple early-stage financings for emerging businesses.
  • Estate planning assistance for two families each with more than one billion dollars of net worth.
  • Represented a founder and his wholly owned investment arm that invested in a large number of startup companies, mostly in the medical device field; work also involved related estate planning work.
  • Regularly perform complex controlled group analyses for numerous family office clients with respect to family ownership of various businesses in connection with retirement, welfare benefit, fringe benefit and nonqualified deferred compensation (Internal Revenue Code Section 409A) issues.
  • Support the design and implementation of household employee payroll and benefit arrangements for HNWIs and their families.
  • Advise in connection with avoiding self-dealing and other Internal Revenue Code prohibitions when private foundations, CLATs or CRTs are part of the family office.
  • Acted as lead counsel in administration of complicated estate involving: (i) sale of international business and settling post-closing income tax issues in multiple jurisdictions including several Chinese provinces; (ii) settlement of federal and multiple state estate tax audits, including post audit claim for refund upon settlement and payment of contingent debt; (iii) wind up of multiple zeroed out GRATs and Notes issued by defective grantor trust; and (iv) preservation of intra-family relationships.
  • Ongoing representation of U.S. citizen in connection with receipt of non-US situs assets from foreign grantor, including termination of foreign non-grantor trust, support to local counsel in creation of foreign grantor trust for U.S. income tax purposes, and preparation of N.Y. irrevocable trust to receive current and future distributions from the foreign grantor trust and foreign grantor; also advise on related U.S. tax reporting requirements as well as the fiduciary income taxation of the N.Y. trust and its administration under N.Y. law.
  • Regularly advise on gift and estate tax planning in the context of a multinational families.
  • Represented corporate fiduciary of deceased client’s will in probate proceeding.
  • Represented corporate fiduciary in connection with settling decedent’s accounting as trustee of various trusts for members of an unrelated family.
  • Drafted and negotiated prenuptial agreements for a number of clients to protect wealth (often multi-generational wealth and/or family business interests) in the event of divorce or death.
  • Used Internal Revenue Service correction program to address retirement plan issues when controlled groups not timely recognized in order to avoid serious adverse collateral consequences to benefit plan design.
They Found Relatives on 23andMe—and Asked for a Cut of the Inheritance
Carole Bass was quoted in the article "They Found Relatives on 23andMe—and Asked for a Cut of the Inheritance," published by The Wall Street Journal [sub. req'd] on November 29, 2025. The article discusses the impact of DNA testing, such as through popular test kits like 23andMe, on inheritance claims, complicating estate settlements and prompting legal challenges when test results reveal unexpected family connections and surprise heirs. States vary in their laws regarding inheritance claims, with some prioritizing genetic ties and others considering the nature of relationships with the deceased. Creating wills or trusts that explicitly address potential claims from unknown biological children is an important step in preventing future disputes. Such clear estate planning documents can help families navigate the challenges posed by unexpected heirs and ensure intentions are honored, Carole said, overriding state definitions of descendants.
Joel Carpenter Selected for Massachusetts Lawyers Weekly Hall of Fame
BOSTON, MA – Massachusetts Lawyers Weekly has selected Sullivan & Worcester Partner, Joel Carpenter, for its 2025 Hall of Fame. Each year, Massachusetts Lawyers Weekly Hall of Fame recognizes attorneys throughout the state with more than 30 years of experience for career accomplishments, contributions to the bar and to the development of Massachusetts law, and efforts to improve the quality of justice. “I’m honored to be included among this year’s Hall of Fame recipients,” Carpenter said. “I’ve had the good fortune to work with highly talented and skilled attorneys and a great leadership team at Sullivan. This recognition also reflects the strength and capabilities of an outstanding law firm.” As former managing partner and co-managing partner of Sullivan for many years, Carpenter has been a guiding force behind the firm’s growth and resilience. He led the firm through the financial crisis of 2008 and again during the unprecedented challenges of the COVID-19 pandemic and helped ensure Sullivan’s steadfast commitment to its clients and values. “Joel has been a defining force at Sullivan for decades, not only through his steadfast leadership during times of challenge and change, but through the extraordinary clarity and judgment he brings to every situation. He has a rare gift for distilling complex problems into clear, actionable choices or reframing them entirely to reveal the path forward. His impact on our firm and clients has been profound, and this recognition is a fitting tribute to his remarkable career and enduring contributions to the legal profession,” said David Nagle, Sullivan’s managing partner. A respected leader in U.S. tax law, Carpenter has significant experience in the tax structuring of complex business and investment arrangements using partnerships, limited liability companies, and Subchapter S corporations. He advises private and institutional investors, including real estate investment firms, on all aspects of U.S. income tax matters related to fund formation, acquisition and disposition of property, structuring debt and equity investments, equity compensation plans, and tax planning for investors. He also advises companies on tax issues related to corporate mergers and acquisitions, financing for emerging companies, and counsels high net worth individuals on income and estate tax planning matters. Carpenter has received numerous professional accolades, including being named to Best Lawyers in America®, 2007-2025, PLC Which Lawyer? Leading Lawyers in Tax, 2008-2010, and Massachusetts Super Lawyers, 2005-2014 and 2017-2018. In addition to his active practice and firm leadership roles, Carpenter has been dedicated to community service and served as a tax advisor to many of Sullivan’s pro bono clients and nonprofit organizations. He was recently elected to the Board of Directors of Pioneer Law Public Interest Law Center (PLPILC), a nonprofit, nonpartisan legal research and litigation public interest law firm. PLPILC defends and promotes educational options, accountable government and economic opportunity across the Northeast and nationwide. The organization works to preserve and enhance liberties grounded in the Constitution and civil rights laws of the U.S. and the New England states. About Sullivan Sullivan & Worcester (Sullivan) is a global, mid-sized law firm with lawyers in Boston, London, New York, Tel Aviv and Washington, D.C. Sullivan’s clients, including Fortune 500 companies, leading financial services firms and asset managers, boards of directors, real estate companies, and emerging businesses, rely on Sullivan’s ability to navigate complex legal and operational landscapes, the impeccable judgment of its lawyers, and its commitment to best‑in‑class client service.