Sydney B. Brady
Sydney focuses her practice on helping clients navigate the emotionally and legally complex world of fiduciary litigation.
She represents individuals—including beneficiaries, trustees, personal representatives, and family members—facing high-stakes disputes involving estates, trusts, and guardianships. With a deep understanding of the sensitive family dynamics that often underlie these matters, Sydney offers practical, strategic guidance that balances her clients’ legal rights with their personal goals.
Sydney’s work spans a wide range of fiduciary matters, from trustee removal and will contests to breach of fiduciary duty and equity actions. She also advises clients in cases where probate and family law intersect—an area that continues to grow in complexity as families become more blended and assets more diverse. In particular, she has extensive experience with disputes involving family trusts, closely held businesses, and the preservation of multi-generational wealth. Sydney is also highly experienced in guardianship matters, regularly working with families navigating the care of minors, young adults with disabilities, individuals impacted by substance use or mental health concerns, and elders.
Known for her clear, candid communication and grounded approach, Sydney partners closely with clients—many acting in a fiduciary role for the first time and feeling overwhelmed. She is a strong litigator and trusted advisor who listens closely, thinks creatively, and keeps the broader picture in focus. Whether negotiating a resolution or litigating in court, Sydney is deeply committed to helping her clients find a path forward that protects both their interests and their relationships. Her collaborative work with financial advisors and other professionals further strengthens her ability to serve clients with complex personal and financial needs.
Trustee Removed Following Trial Victory
Second-chaired a successful trustee removal trial in the Fiduciary Litigation Session, resulting in the court removing the trustee for misconduct. The judgment required the trustee to repay funds misused from the trust and awarded a substantial portion of the petitioner’s legal fees.
Preserving Family Relationships Outside the Courtroom
Advised personal representatives, trustees, and other fiduciaries facing complex family and financial challenges. Helped clients resolve disputes without litigation, protecting family privacy and promoting long-term relationship preservation through thoughtful, proactive counsel.
Education
- JD, Boston University School of Law, 2019
- BA, Smith College, 2014
Bar Admissions
- Massachusetts
Experience recognized
- Best Lawyers Ones to Watch, Family Law, 2024-2026
- Massachusetts Super Lawyers, Rising Stars, 2024-2025
- Social Justice Mediation Certification, Social Justice Mediation Institute, Amherst, MA
- Fiduciary Litigation Year in Review, Social Law Library (January 2025, Presenter)
- Representing Grandparents as Guardians, Massachusetts Continuing Legal Education (October 2024, Speaker)
- Ask the Experts, Jane Does Well (July 2024, Speaker)
- Alimony, Child Support, and Co Parenting, Vesta Divorce Boston (July 2024, Speaker)
- Fiduciary Litigation in the Probate Court, Massachusetts Continuing Legal Education 6th Edition (2024, Co-Author)
- Dating and Introducing the Kids After Divorce, Vesta Divorce Boston (May 2024, Speaker)
- Finding Hidden Assets in Divorce, Vesta Divorce Boston (April 2024, Speaker)
- The Mid-Life Divorce, Vesta Divorce Boston (March 2024, Speaker)
- Trusts and Estates Course – Will Contests, Suffolk University School of Law (March 2024, Guest Lecturer)
- Career Day, Huntington YMCA (February 2024, Panelist)
- How to Successfully Navigate the Divorce Process, Vesta Divorce Boston (February 2024, Speaker)
- Probate and Family Court’s Fiduciary Litigation Session Year-in-Review, Social Law Library (January 2024, Speaker)
- Meet the Small/Midsize Firms, Boston University School of Law First Generation Professionals (November 2023, Panelist)
- Ask the Experts, Jane Does Well (May 2022, Speaker)
- Ask the Experts, Jane Does Well (December 2022, Speaker)
- Friends School Mullica Hill, Board of Trustees, Mullica Hill, NJ
- Boston Bar Association, Senior Associates Forum