Leo

J.

Cushing

Leo is a Boston native who attended Boston Latin School and then the University of Notre Dame where he earned a Bachelor’s Degree in Science/Accounting. Leo then attended New England Law Boston, where he obtained his J.D. 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 became a tax professional at the international accounting firm of Ernst & Young (f/k/a Ernst & Whinney) where he earned his certification as a Certified Public Accountant. During this time, Leo also attended the Boston University Law School Graduate Tax Program where he earned his Masters 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. 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, charitable giving and fiduciary litigation involving trusts, estates, probate matters and shareholder disputes.

Leo has lectured extensively since 1984. In 2018, he was awarded from M.C.L.E. a Scholar Mentor Award for his 30 years of service in lecturing in over 80 programs on behalf of M.C.L.E. and authored numerous textbooks, including the standing volume “Preparing Fiduciary Income, Gift, and Estate Tax Returns” currently in it’s 2nd Edition. Leo currently teaches Partnership Taxation at Boston University Law School in their Graduate Tax Program, having previously taught Income Taxation of Decedents Estates and Trusts for seven years. 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.