Caroline F. Trainor
For Caroline, family has always been at the center of life—a value instilled early by parents who emphasized the importance of showing up for one another.
That perspective guided her toward a career in estate planning, where she helps individuals and families navigate both joyful milestones and challenging transitions with clarity, compassion, and foresight.
She represents a broad spectrum of clients, from single individuals and young families to business owners and high-net-worth individuals with complex planning needs. Known for her ability to simplify intricate legal and tax issues, she works closely with clients to design estate plans that not only protect wealth but also preserve family harmony across generations.
Her practice includes advising on wills, trusts, and succession planning for family businesses, as well as ensuring that every detail of a plan is in place to provide peace of mind. She brings particular strength in crafting tax-efficient strategies, blending her affinity for numbers with a deep commitment to helping clients achieve their personal and financial goals.
Above all, she approaches her work with empathy—whether she is guiding a family through the loss of a loved one or helping them prepare for the future. Clients value her ability to combine technical skill with genuine understanding, making the process of estate planning both accessible and reassuring.
Restructuring Family Business to Preserve Wealth Across Generations
Guided a multigenerational family in restructuring business operations across multiple entities, transferring partial ownership to the next generation while allowing parents to retain managerial oversight. Established irrevocable trusts to safeguard children’s business interests, ensuring creditor protection and tax efficiency—ultimately securing an estimated $50 million in estate tax savings.
Supporting Estate Administration Through Personal Loss
Assisted a daughter in administering her parents’ estate following the deaths of her father, brother, and mother within a span of 18 months. Provided not only legal guidance to ensure a smooth administration but also compassionate support during a period of profound personal loss.
Education
- JD, Santa Clara University School of Law, 2019
- Jiao Tong Law School, Chinese and International Business Law, 2017
- BA, Loyola University Maryland, Global Studies, 2016
Bar Admissions
- Massachusetts
- California
Experience recognized
- Massachusetts Super Lawyers, Rising Stars, 2025
- Readdressing Irrevocable Life Insurance Trusts, BASF (February 2023)
- Overview of Irrevocable Life Insurance Trusts (ILITs) for Estate Planning and Gift Tax Return Purposes, SMCBA (February 2023)
Exploring the Great Outdoors
An avid hiker, she finds joy in exploring trails near and far, with memorable treks through the Grand Canyon, Zion National Park, and Australia’s Blue Mountains. Always eager for the next adventure, she hopes to add many more destinations to her hiking list.
A Passion for the Written Word
A dedicated reader, she keeps a growing list of books to finish and never limits herself to a single genre. From musical biographies to fantasy and historical non-fiction, her reading interests reflect a curiosity as wide-ranging as her professional work.
Creative Expression Through Art
With a deep appreciation for artistic expression, she enjoys both creating and observing art. Whether teaching herself painting and pottery or visiting museums to study different mediums, she embraces opportunities to learn, appreciate, and create.