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Anthony J Dragga.


Anthony J. Dragga



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.”



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


  • Former Director, Board of Directors, St. Camillus Health Center


  • 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


  • 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

Summary Judgment victory in a difficult contractual claim

When another party failed to build key, agreed-to components of a major construction project, the principal developer turned to Tony and the firm for help. With tens of millions of dollars at stake, our client obtained Summary Judgment on damages, which Tony drafted, thereby avoiding a trial. “There wasn’t much case law to rely upon for the Summary Judgment argument,” Tony noted, “which called for creative legal reasoning, and a certain amount of common sense, to persuade the court.”

Resolving a favorable withdrawal from a professional healthcare services partnership

A member of a health care practice wasn’t getting along with the other two members of their LLC, based on money and personality issues. “We filed a pre-emptive suit to stop her partners from forcing her out,” Tony explained. “That allowed time for us to negotiate a settlement favorable to our client, which included withdrawing from the LLC, resolving compensation issues and coming to an agreement on non-compete terms.” 

Other experience

  • Position statements for filing with the Massachusetts Commission Against Discrimination and Equal Employment Opportunity Commission in employment discrimination and retaliation claims
  • Electricity and gas company as plaintiff in negligence actions
  • Civil engineering firm in its dispute with a local municipality over unpaid bills for services rendered
  • Responses to demand letters sent to employers alleging breach of contract, unlawful termination and tort-based claims
  • Counseled a national employer in the healthcare sector regarding wage and hour and other legal requirements pertaining to working conditions in 32 states, including meal breaks
  • Employee Loan Agreements for a major Massachusetts employer
  • Written Information Security Program Policy (WISP) for a college
  • Assisted with the strategic and preemptive preparation of a complaint and request for injunctive relief to be filed in state court for the firm’s client, a college challenging a proposed Department of Elementary and Secondary Education administrative decision, which would have negatively impacted the accreditation status of the institution’s professional certification programs
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