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Roland Gray III

Photo of LF Boston Attorney Roland Gray

Roland (Rob) Gray III



Boston University School of Law

Stanford University

Bar & Court Admissions

  • Massachusetts
  • Vermont
  • United States Tax Court

Rob has been in legal practice for more than four decades—and he belongs to the ninth unbroken generation of lawyers and trustees in the family. But he is quick to say, “I didn’t know I was going to like the law until I got into it. It’s been—and continues to be—greatly satisfying to provide education and assistance that positively influences people’s lives both economically and personally.”

Indeed, some of his clients from 40 years ago are still with him, as are their children and grandchildren. For them and others, he primarily handles trusts and income and estate tax planning; Medicaid, Medicare, and transitional assistance planning; and professional trustee law.

Rob oversees approximately 375 trusts with a combined market value in excess of $250 million. In his practice, he:

  • Handles estate, income, and gift-tax planning for individuals and families;
  • Acts as a professional trustee of trust funds;
  • Assists clients to qualify for Medicare, Medicaid, and other public assistance benefits (and continue to qualify);
  • Advises on matters including estates, guardianships, and conservatorships;
  • Assists clients and their families in obtaining needed medical and psychiatric intervention services for loved ones.

To help prevent clients from losing their way through such challenges as tax difficulties, addiction, mental illness, disability, or matters of the heart, Rob calls upon an extensive network of multidisciplinary professionals. Acting as a knowledgeable gatekeeper, Rob makes these discreet and expert resources available to caretakers, clients, and their families—providing respectful, individualized counsel throughout the life cycle.

Rob also maintains a strong commitment to accessibility, reserving a portion of each week to seeing first-time clients, providing assessments to ensure that they receive the kind of legal attention appropriate to their needs.