Anthony J. Dragga

Overview

Tony Dragga is a highly regarded Partner in the firm’s Estate, Financial & Tax Planning Practice Area, helping clients in Massachusetts with a variety of matters, including the preparation and administration of estates and estate plans. Business owners, distinguished professionals, senior executives, and high net worth individuals turn to Tony to develop personalized plans to reduce or eliminate estate, gift, and income taxes. Clients also rely on Tony in a variety of matters including the investment and division of assets, identification and appraisal of estate and trust assets, preparing and filing federal and state estate tax returns, and collection of life insurance and employee benefits.

Tony approaches each unique situation on a personal level, understanding the client’s specific needs, whether it be financial planning, personal estate planning, post-death tax planning, investment management, and more. Clients value Tony’s listening skills, patience and analytical abilities. “I love to tackle big problems,” he adds, “and my teaching background is an advantage.”

Before Bowditch

Tony’s interest in higher education and experience with issues impacting educational institutions predate his legal career. He was a teacher and administrator at the Nativity Preparatory School of New Bedford, Massachusetts. He also earned a Master of Arts in Higher Education Administration at Boston College’s Lynch School of Education.

During law school, Tony clerked for the General Counsel’s office at Northeastern University. Tony also clerked for Bowditch in 2013 and joined the firm full-time in fall 2014. Prior to joining the firm’s Estate, Financial & Tax Planning group, Tony served over five years in the Business Litigation and Employment Law groups.

Besides work

Tony’s a former high school athlete who lettered in swimming. “Nowadays, I like to run. Otherwise, I follow the Orioles and play along with Jeopardy! in my spare time.”

Affiliations

President & Member, Executive Committee, Central Massachusetts Estate and Business Planning Council
Treasurer, Board of Directors, Blackstone Valley Chamber of Commerce
Board of Directors, ArtsWorcester
Member, Worcester County Bar Association
Member, Leadership Worcester Class of 2016

1st Vice President, Estate and Business Planning Council of Worcester County
Director, Board of Directors, St. Camillus Health Center

Honors

Best Lawyers in America: Ones to Watch, for the field of Trusts and Estates (since 2022)
Community Legal Aid 2020 Pro Bono Honor Roll

Articles + Talks

Tony frequently writes on employment and higher education issues and regularly contributes to the firm’s blog and monthly newsletter about legal issues affecting colleges and universities, Campus Counsel. He recently co-authored an article published in the New England Journal of Higher Education discussing on-campus and online student free speech challenges for institutions of higher education and presented on the topic for the firm’s College & University Roundtable Series. In an article published in Boston Business Journal, Tony investigated workplace drug policies in light of the changing legal landscape and growing social acceptance of medicinal and recreational marijuana use.

Bar Admissions

Massachusetts
United States District Court for the District of Massachusetts

Education

LL.M., Master’s in Taxation, Boston University School of Law
J.D., Boston College Law School
M.A. Higher Education Administration, Boston College
B.A., Boston College

Experience

Represents both fiduciaries and beneficiaries in contested estate and trust administrations. When a loved one passes away, clear communication and transparency are critical in order to minimize costly family conflict. Tony regularly advises trustees and Personal Representatives (as well as non-fiduciary beneficiaries) so that they may better understand their rights and obligations in the estate and trust administration process.
Irrevocable trust modifications, both inside and outside of the probate court setting to achieve favorable income and estate tax objectives. Tony has significant experience in trust modification matters, particularly in instances where there has been a change in relevant tax law or where the trust, as drafted, does not achieve the Grantor’s intent. In a recent case, Tony was retained by a family to modify an irrevocable trust which designated approximately $5M to pass to charity. The trust contained a drafting error, and as drafted, the trust did not qualify for the estate tax charitable deduction, leading to an estate tax assessment of approximately $500,000. Tony successfully petitioned the Court to modify the terms of the trust so that the estate tax charitable deduction could apply, thereby wiping out the estate tax obligation.
Serves as trustee of numerous trusts and as Personal Representative of various estates

Insights + News