Winston Duggan

Attorney, Estate Planning at CunninghamLegal

This compassionate, attentive attorney brings an unfailing sense of calm and understanding to what might otherwise be intimidating, harrowing experiences for his clients.

Winston Duggan loves to solve problems for families going through difficult moments and make their lives easier. Well aware that many of his clients walk through his door for the first time with a sense of worry, panic, and very often grief, he calms their nerves and addresses their fears. Indeed, his innate ability to shepherd people through tough transitions brought this level-headed, communicative, and highly experienced attorney to the field of Estate Planning in the first place.

“I pride myself on being a source of calm, stability, and comfort for our clients, taking care of their estate plan or administering their trust, so that they can spend less time worrying and more time enjoying life with their families.”

Graduating from Santa Clara University School of Law, Winston received a CALI Award in Juvenile Law Seminar, which means he had the highest grade in the class. Before joining the CunninghamLegal team, he worked at several prestigious law firms in the Bay Area and completed an internship with the Northern California Innocence Project. Always seeking ways to help people, he also interned in a division of the Santa Clara County Public Defender’s office that concentrated exclusively in juvenile delinquency. It was a position that allowed him to help “steer kids in the right direction and to learn from their mistakes.” His B.A. was in Political Science (Law and Politics) from Marquette University. With a deep interest in helping children and families, he also has a strong background in family law.

Steady and Supportive

As an Estate Planning attorney, Winston has experience in all areas of the discipline, from drafting complex Living Trust and related documents to administering trusts and representing clients in probate court. Indeed, he calls Estate Planning his “true calling,” as it better enables him to make a difference: how better to make sure clients know their families would be okay if something happened to them?

Recently, for example, a client of Winston’s received sudden and fearful news that he did not have much more time to live. Although there was an Estate Plan, it was woefully out of date—and Winston moved fast, while acting as a stabilizing presence for the whole family in its time of crisis. Working through the client’s complex family issues, Winston made many critical adjustments, including updating the client’s trust beneficiaries to include his newly born grandchildren, and adjusting healthcare documents to ensure the client’s current partner would be able to make healthcare decisions on his behalf when the time came. Of the experience, Winston says, “It was a difficult time for all involved, but we were able to do what we could to help and provide some sense of comfort and relief.”

Another of Winston’s recent accomplishments was drafting an appellate brief that was successful in overturning a $50,000 sanction against his client. Appeals are rarely successful, but he was able to save the client $50,000.

When asked what makes him most proud as an attorney, Winston gives an answer truly indicative of his dedication to his clients and his commitment to the practice of law: “The accomplishments I am most proud of generally come from successful litigation and securing positive outcomes for my clients, but I am genuinely proud any time a client is moved to say thank you and that they appreciate the work I have done.”

Given that answer, it’s not surprising that clients frequently remark on Winston’s consistent ability to carefully listen to all concerns and address every problem, keeping them in the loop every step of the way.

Out and About in His Personal Life

With weekend jaunts to the Wine Country or day trips to Tomales Bay for oysters, Winston and his fiancée love spending time exploring the Northern California area he serves. Lake Merritt and Pt. Reyes are particular favorites, and the two say they love the fact that there is always something new to explore or do here.

From shopping at local farmer’s markets to trying new restaurants, this foodie tempers his love of good cuisine with trail running, golf, and Peloton sessions. An avid sports fan who grew up with season tickets to the Giants, he loves to cheer on area teams like the 49ers, Warriors, and of course, the Giants. Over the years, Winston has also made a point of volunteering at area food banks.

Contact Us Today

Winston Duggan and our full team of attorneys can help you with advanced Estate & Tax Planning from any of our offices throughout Northern and Southern California. We offer in-person, phone, and Zoom appointments. Request an appointment online or call (866) 988-3956.

At CunninghamLegal, we guide savvy, caring families in the protection and transfer of multi-generational wealth.

Attorney Winston Duggan