MassMutual financial professional.

Gary Sancilioemail

Gary Sancilioemail


Charter Oak Financial: The Holyoke Office

330 Whitney Avenue #600
Holyoke, MA 01040

Professional Story

For more than 34 years, I have helped individuals and families navigate insurance and financial protection planning with a practical, client-focused approach.   My background in law allows me to bring a thoughtful, straightforward perspective to the planning process, particularly for those who have spent years building wealth and want guidance on protecting what they have achieved while preparing responsibly for the future.

I believe meaningful planning begins with understanding people, not products. My priority is building long-term relationships with clients and developing insurance-focused risk management and protection strategies tailored to their unique goals and circumstances. These strategies may include income protection planning, estate planning considerations, and legacy objectives designed to support long-term financial security.

I earned my Juris Doctor degree from St. John’s University School of Law. After being admitted to the New York Bar, I served as an Appellate Court Attorney and later as an Assistant District Attorney in New York City before entering private legal practice. Although I am no longer a practicing attorney, my legal experience continues to provide valuable perspective when working alongside clients’ attorneys and tax professionals on matters involving estate planning, business succession considerations, and wealth transfer strategies. I also remain a member of the Trusts and Estates Section of the New York State Bar Association.

Community involvement has always been important to me. I actively support several local charitable organizations through both volunteer efforts and personal involvement. I am especially proud to support the Make-A-Wish Foundation, an organization dedicated to granting wishes to children facing critical illnesses.


Languages: English


Specialties:Estate Planning, Risk Management Strategies, Insurance Strategies