Leo

J.

Cushing

Leo J. Cushing is the founding partner of Cushing & Dolan, P.C., a Waltham-based law firm established in 1984. A Boston native, Leo attended Boston Latin School and then the University of Notre Dame, where he earned a Bachelor of Science degree in Accounting. He then attended New England Law Boston, where he obtained his J.D., cum laude, while working full time as a forensic accountant for Attorney General Francis X. Bellotti of the Commonwealth of Massachusetts.

Following law school, Leo was appointed an Assistant Attorney General in the Criminal Bureau where he prosecuted criminal tax cases and defended the Commonwealth of Massachusetts against various claims including post-conviction relief matters and civil rights matters involving state officials.

Following his tenure as an Assistant Attorney General, Leo joined the international accounting firm of Ernst & Young (f/k/a Ernst & Whinney) as a tax professional, where he earned his certification as a Certified Public Accountant. During this time, he also attended the Boston University School of Law Graduate Tax Program, where he earned his Master of Laws in Taxation.

Leo entered private practice in 1984 and founded Cushing & Dolan, P.C. The firm, currently based in Waltham, Massachusetts, employs approximately 20 attorneys and 45 employees overall. Leo's practice includes all aspects of sophisticated estate planning techniques, asset protection, trust planning, charitable giving, and resolution of tax controversies. The firm concentrates on complex estate planning for owners of closely held businesses and wealthy individuals, commercial and residential real estate, elder law, tax planning, corporate transactions, tax representation, and fiduciary litigation involving trusts, estates, probate matters, and shareholder disputes.

A strong advocate for education, Leo has written and lectured extensively on all aspects of taxation and estate planning since 1984.  In 2025, he was inducted into the Massachusetts Lawyers Weekly Hall of Fame. The Hall of Fame selection criteria includes career accomplishments, contributions to the development of the law in Massachusetts, contributions to the bar, and efforts to improve the quality of justice in Massachusetts. 

In 2024 and 2026 Leo was selected as one of Massachusetts Lawyers Weekly's Go To Taxation Lawyers.

In 2018, Leo was awarded the MCLE Scholar Mentor Award for his 30 years of service lecturing in over 80 programs. He has authored numerous textbooks, including the standing volume “Preparing Fiduciary Income, Gift, and Estate Tax Returns," currently in its 2nd Edition.

For over a decade, Leo taught Partnership Taxation and Income Taxation of Decedents Estates and Trusts at Boston University Law School in their Graduate Tax Program. He has been a speaker for REBA, the Massachusetts Bar Association, Boston Estate Planning Council, Massachusetts Association of Accountants, Massachusetts Society of CPAs, American Institute of CPAs, National Business Institute, Foundation for Continuing Education, Avidia Bank, Community Foundation of North Central Massachusetts, and Massachusetts Estate and Retirement Planning Council.

Leo is a former member of REBA's Board of Directors and co-chair of its Estates and Trusts Section, where he reviewed and provided commentary and opinions on pending legislation and case law affecting real estate and trust/probate matters. He is also a former director of the Boston Estate Planning Council.

Leo lives in Lexington, is married and has two children.

For over a decade, Leo taught Partnership Taxation and Income Taxation of Decedents Estates and Trusts at Boston University Law School in their Graduate Tax Program. Leo was a proud and active member of the Massachusetts Real Estate Bar Association (REBA) where he chaired the Estate Planning, Trusts and Estate Administration Section devoted to reviewing and providing commentary and opinions on pending legislation and case law affecting real estate and trust/probate matters.

Leo lives in Lexington, is married and has two children.