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Jessie A. Gilbert is a Principal in Cummings & Lockwood's Private Clients Group and is based in the Greenwich office. Jessie advises high net worth individuals on estate and tax issues, helping them with succession, generation-skipping and asset protection planning. She also represents executors and trustees with respect to probate, estate and trust administration matters, as well as with estate and fiduciary income taxes.

Jessie is a frequent writer and lecturer on estate planning and administration topics, including business succession planning, fiduciary income tax, and the Principal and Income Act. She has also served as a law clerk with the United States Tax Court in Washington, D.C.

In her spare time, Jessie enjoys acting in community theater productions and practicing karate, in which she has a black belt.


  • Two Greenwich Plaza
    Greenwich, CT 06830-6390


  • New York University, L.L.M., graduated 1986
  • Case Western Reserve University, J.D., graduated 1985
  • Hamilton College, A.B., graduated 1982

Bar Admissions

  • Connecticut, 1989
  • New York, 1986


  • Connecticut Bar Association - Member
  • Estate Planning Council of Lower Fairfield County - Member
  • Greenwich Bar Association - Member
  • Westport Country Playhouse - Board of Trustees
  • Darien Arts Center - Past Board Member

Federal Clerkships

  • United States Tax Court

Recognized in The Best Lawyers® in America 2023 for work in:

  • Trusts and Estates


  • Connecticut and New England Super Lawyers, 2007
  • Martindale-Hubbell, AV Rated

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