Leo J. Cushing Esq., CPA, LLM

E-mail MeLeo J. Cushing Esq., CPA, LLM

Waltham, Massachusetts
Direct Line:
(781) 314-1908
Main Line:
(617) 523-1555 Ext. 1908
Toll Free:
(888) 759-5109
Main Fax:
(617) 523-5653
Direct fax:
(781) 314-1054

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 Boston Bar Association, The Massachusetts Bar Association, The National Academy of Elder Law Attorneys, The American Institute of CPAs, The American Academy of Attorney-CPAs, The Boston Tax Council and The Boston Probate and Estate Planning Forum. He is a Co-Chair of The Estate Planning, Trusts & Estate Administration Committee for The Real Estate Bar Association for Massachusetts. He is also on the Board of Directors for The Real Estate Bar Association for Massachusetts. In 2010, Leo was appointed to The Notre Dame Law School Advisory Council. In 2010, Leo was also appointed a Lecturer in Law at Boston University School of Law's Graduate Tax Program.

Leo has written and lectured extensively on all aspects of taxation and estate planning. 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 has been a speaker for The Boston Estate Planning Council, The Massachusetts Bar Association, The Real Estate Bar Association for Massachusetts, The Massachusetts Association of Accountants, The Massachusetts Society of CPAs, The American Institute of CPAs, The National Business Institute, The Foundation For Continuing Education, Avidia Bank and The Community Foundation of North Central Massachusetts and the Montachusett Estate and Retirement 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.

Areas of Practice

  • Estate Planning
  • Business Law
  • Tax
  • Elder Law
  • Real Estate

Bar Admissions

  • 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

Honors and Awards

  • Massachusetts Super Lawyers, 2005 - 2016

Professional Associations and Memberships

Rated by Super Lawyers 
  • 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