Leo J. Cushing Esq., CPA, LLM
Leo J. Cushing is the founding Partner of Cushing & Dolan, P.C., a Boston based law firm established in 1984 specializing in closely held businesses, taxation, sophisticated estate planning, elder law and real estate. Leo's practice includes all aspects of sophisticated estate planning techniques, asset protection, trust planning, charitable giving and resolution of tax controversies. Prior to establishing Cushing & Dolan, P.C., Leo earned his certified public accountant designation while working as a tax professional for the international accounting firm of Ernst & Young. Prior to Ernst & Young, Leo served as an Assistant Attorney General for the Commonwealth of Massachusetts where he prosecuted criminal tax cases and defended the Commonwealth of Massachusetts in various civil claims against state agencies.
Leo is a former Director of the Boston Estate Planning Council. He is a member of the Massachusetts Bar Association, the American Institute of Certified Public Accountants, American Association of Attorneys and CPAs, the Boston Estate Tax Council, Boston Bar Association and the National Association of Elder Law Attorneys. Recently, Leo was appointed to the Notre Dame Law Advisory Council for a three-year term beginning in 2011, and has once again been named one of Massachusetts Super Lawyers in 2011. He was also named a Five Star Wealth Manager in Boston in 2010, 2011, and 2012. Leo was recently appointed Lecturer in Law at the Boston University Law School’s Graduate Tax Program.
Leo has written and lectured extensively on all aspects of taxation and estate planning. He served as Editor in Chief and Program Chair of the Massachusetts Continuing Legal Education program (MCLE) entitled, "Preparing Estate Tax Returns." Leo was also a contributing author and lecturer at MCLE's program entitled, "Preparing Fiduciary Income Tax Returns" as well as its "Advanced Issues in LLCs."
Leo is a much sought after speaker as he is able to articulate complex issues in a way that is clear, concise and easy to understand. Recently, Leo chaired MCLE's program entitled, "What Every Lawyer Should Know About Life Insurance Planning for Businesses & Individuals" and "Medicaid Planning & Medicare Set-Asides." In addition, Leo taught "Use of Limited Liability Companies and Family Limited Partnerships In Long Term Care Planning" for Suffolk Law School's Advanced Legal Studies. At the 2010 CPAmerica International Tax Conference, Leo lectured on "Estate, Gift, and Fiduciary Taxes – Recent Developments" and "U.S. Estate and Gift Implications of Foreign Transactions. Leo has also spoken at the American Bankers Association Advanced Trust Forum, the Massachusetts Society of Certified Public Accountants Annual State Tax Meeting, and the Boston Estate Planning Council.
Leo is a graduate of Boston Latin School, and he earned his Bachelors of Science in Accounting at the University of Notre Dame. He also earned his J.D., cum laude, from the New England School of Law, and his Master of Laws in Taxation from the Boston University School of Law. Leo is also a Certified Public Accountant.
Leo is married with two children and currently lives in Lexington, Massachusetts.
Certified Legal Specialties
- Public Accountant, International Accounting Firm of Ernst Whinney
- Public Accountant, American Association of Attorneys and CPAs
- Attorney Cushing concentrates his practice on advising wealthy families and business owners on taxation, business succession, and asset protection
- Massachusetts, 1980
- New Hampshire, 2008
- U.S. District Court, 1981
- U.S. Supreme Court, 1984
- U.S. Tax Court, 1984
- Boston University School of Law, Boston, Massachusetts
- L.L.M. - 1985
- Major: Taxation
- New England School of Law, Boston, Massachusetts
- J.D. cum laude - 1980
- University of Notre Dame
- B.S. - 1975
- Major: Accounting
- Editor in Chief, "Preparing Estate Tax Returns", MCLE
- "Preparation of Fiduciary Income Tax Returns", MCLE Publication
- "New Massachusetts Estate Tax Law; Trouble for Conveyancers", Massachusetts Lawyer's Weekly, December, 2002
- "Lifetime Giving with Intentionally Defective Irrevocable Grantor Trusts", Massachusetts Lawyer's Weekly, December, 1999
- "Knowing Generation Skipping Rules is Key", Massachusetts Lawyer's Weekly, December, 2000
- "Family Limited Partnerships Too Good to be True", Boston Business Journal
- "A Road Map to Successful Split Dollar Arrangements", Journal of Asset Protection, Nov/Dec., 1995
- "Joint Trust Revolutionize Estate Planning for Retirement Assets and Estates Under $3,000,000 for Couples", Massachusetts Society of CPAs, Spring, 2005
- "Preparing Fiduciary Income, Gift, and Estate Tax Returns", MCLE, 2011
- Speaker, Estate Planning, Asset Protection and Elder Law Matters, Continuing Legal Education Programs
- Speaker, Estate Planning, Asset Protection and Elder Law Matters, Tax Institutes
- Speaker, Estate Planning, Asset Protection and Elder Law Matters, Massachusetts Continuing Legal Education (MCLE)
- Speaker, Estate Planning, Asset Protection and Elder Law Matters, Foundation for Continuing Education
- Speaker, Estate Planning, Asset Protection and Elder Law Matters, Boston Estate Planning Council
- Speaker, Estate Planning, Asset Protection and Elder Law Matters, IPE/National Business Institute
- Speaker, Estate Planning, Asset Protection and Elder Law Matters, National Association of Insurance and Financial Advisors (NAIFA)
- Speaker, Estate Planning, Asset Protection and Elder Law Matters, Boston Security Analysts Society
- Speaker, Estate Planning, Asset Protection and Elder Law Matters, Financial Planners Association
- Speaker, Estate Planning, Asset Protection and Elder Law Matters, Massachusetts Rental Housing Authority
- Speaker, Estate Planning, Asset Protection and Elder Law Matters, Boston Bar Association
- Speaker, Estate Planning, Asset Protection and Elder Law Matters, Massachusetts Bar Association
- Speaker, Basic Estate Administration, Massachusetts Paralegal
- Speaker, Annuities, Trusts and Long Term Care Insurance & Medicaid Planning
- Speaker, Advanced LLC Topics: Advising Clients on Complex LLC Operations & Transactions
- Speaker, Zero Estate Tax Planning: The Sale of Assets to an Intentionally Defective Grantor Trust The Ultimate Estate Tax End Game
- Speaker, Income Taxation of Trusts & Estates
- Speaker, Advanced Estate Planning
- Speaker, Effective Wealth Transfer Planning with Family Limited Partnerships
- Speaker, A Survival Guide to Estate Planning in Massachusetts Under the New Massachusetts Act
- Speaker, Tax Practice, Northeastern University Graduate Tax Program
- Speaker, Taxation and Estate Planning
- Speaker, "Advanced Issues in LLC's, covering the topics, "Using an LLC to Consolidate Family Assets to Facilitate Succession Planning and Save on Gift and Estate Taxes"
- Speaker, "Successful Planning for the Family Business - Buy/Sell Agreements, S Corporations and Lifetime Giving & Sales to Intentionally Defective Grantor Trusts"
- Speaker, "A Comparison of Lifetime Giving and Transfer Techniques, including GRATs, GRUTs"
- Speaker, Sales to Intentionally Defective Trusts Using Self-Canceling Notes and Private Life Annuities"
Honors and Awards
- Massachusetts Super Lawyers, 2005 - 2011
- Boston Five Star Wealth Manager, 2010 - 2012
Professional Associations and Memberships
- Notre Dame Law School Advisory Council, Member
- Massachusetts Bar Association, Member
- American Institute of Certified Public Accountants, Member
- American Association of Attorneys and CPA's, Member
- Boston Estate Tax Council, Member
- Boston Bar Association, Member
- Boston Estate Planning Council, Former Director, Member
Past Employment Positions
- International Accounting Firm of Ernst Whinney, Tax Attorney, 1982 - 1984
- Assistant Attorney General Criminal Bureau, Prosecutor, 1980 - 1982
- Attorney General's Office of the Commonwealth of Massachusetts, Forensic Accountant, 1975 - 1980