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Jaclyn S. O'Leary

Boston, MA

A Trusted Navigator

Jaclyn O'Leary wanted a career focused on helping others. With many of her family members in law enforcement, Jaclyn considered becoming a lawyer as a pathway to a career as a crime-fighting federal agent. But while working her way through law school as a paralegal at a boutique trusts and estates firm, Jaclyn's interest in that practice area emerged unexpectedly.

She never looked back. While immersed in her studies, Jaclyn found she had a knack for the personal aspect of working closely with the firm's clients. "One of the things I enjoy most about my practice is that you really get to know your clients," she said. "By closely interacting and listening to their concerns, I am able to tailor solutions specific to their individual needs. It's gratifying to provide peace of mind with successful estate planning strategies."

A member of Day Pitney's Trusts and Estates practice, Jaclyn advises high net worth families and individuals on estate planning and tax matters. She works with clients to implement comprehensive estate plans and guides them through estate administration, addressing any complex estate, trust, probate and tax matters that may arise in the process.

Jaclyn joined Day Pitney in its Boston office at the end of 2012, a time when the federal estate tax exemption was expected to drop significantly in a matter of weeks and many clients sought urgent and efficient wealth preservation guidance. She embraced that challenge by adapting quickly to develop solutions for clients and continues to stay ahead of emerging strategies in response to changes in state and federal tax laws.

In addition, Jaclyn serves as a trustee and advises trustees on proper administration of trusts, distribution of trust assets and communications with beneficiaries. She also handles contested probate matters, resolving conflicts by listening to concerns and helping parties understand underlying tax and planning issues that can lead to conflicts.

Clients appreciate Jaclyn's ability to handle legally complex matters, including those rife with delicate interpersonal considerations and emotions. "It's refreshing to work with someone who can navigate it all with a positive attitude, empathy where required, and importantly, a sense of humor," said Mark Andersen, vice president and senior wealth strategist at Wilmington Trust. "Jaclyn brings the perfect blend of technical excellence, attention to detail and strategic thinking to her client engagements. I couldn't ask for more in an attorney."

When she's not practicing law, Jaclyn enjoys running, traveling and devoting time to charitable pursuits. She has served as a volunteer advocate at the Victim Rights Law Center in Boston and helped raise funds for public service projects of the Boston Bar Association. In 2017, Jaclyn ran the Boston Marathon as part of the Dana-Farber Marathon Challenge, raising funds to benefit the Dana-Farber Cancer Institute.