On January 1, 2025, BW principal Brian T. Silvestro announced his retirement, transitioning his status to of counsel. While Brian will no longer be taking on new matters, he will continue to support the firm in this new capacity for the foreseeable future. To mark the occasion, we invited Brian to reflect on the last 50 years and share his plans for tomorrow.
Q: What motivated you to pursue a career in law and how did that motivation mature over the years?
A: I graduated from Wesleyan University in 1970. I always intended to go to law school believing that a legal education would be valuable no matter where my career choice took me. However, I decided to take a gap year before law school and accepted a sales job at Proctor & Gamble. I enjoyed the competition of sales so much that I continued working there while attending law school at night. My experience in sales proved invaluable long after I left the job. The skills I developed — particularly the ability to connect with people and negotiate transactions — helped me create a successful law practice and a strong client base. As my practice progressed, I realized that the most important part of my work was building relationships based on mutual respect and trust. Closings were not won or lost in my mind. They were successfully accomplished to both parties’ mutual benefit.
Q: How did the legal landscape evolve during your career and how did you adapt to the changes?
A: I have always practiced residential real estate law. The field itself over time has become increasingly adversarial. I miss the old days when transactions felt more collaborative. Technology has also transformed how law is practiced. Within my specific niche, in-person closings which were once the norm are now the exception. The shift toward remote representation and virtual proceedings accelerated during the pandemic, making the process more efficient but less personal. Despite my nostalgia for the old days, I know my clients appreciate the flexibility and conveniences that technology provides today.
Q: Can you discuss a particularly challenging matter or legal issue you encountered and how you navigated it?
A: Spanning the past 50 years, I have navigated countless challenges. The hardest one involved the sale of a waterfront property in Westport owned by a celebrity client and his wife. The transaction was very complex and contentious, made even more difficult for me to handle due to my mother’s health at the time. Yet, my client’s empathy and straightforwardness made all the difference. We got through it together because of the mutual trust and respect we built, which was an overarching focus of my practice. I will always remember his authenticity and kindness. I will cherish the enduring friendship we shared until his passing.
Q: Can you share a memorable milestone or highlight that stands out in your career?
A: There have been many milestones and highlights along the way but perhaps the most meaningful has been the response from peers and clients regarding my recent retirement. Being recognized as a good lawyer who will be missed is both humbling and gratifying.
Q: What advice would you give to aspiring lawyers starting their careers today?
A: My advice would be to never lose sight of a lawyer’s vital role as a counselor and trusted advisor. I often compared my work to that of a family physician — clients relied on me to look out for them, identify potential issues and help resolve their challenges. Striving to meet their expectations not only strengthened those relationships but also contributed to smoother real estate transactions for all parties involved.
Q: What are you planning to do in your “Third Act?”
A: I am excited to put my basketball coaching experience and school counseling license to use! I will be serving as a volunteer assistant for the local high school basketball team, where I previously spent many years coaching. In this new role, I will be working with both varsity and JV student-athletes, helping them develop their technical skills while also providing general counseling to support their growth on and off the court. In addition, I am currently taking some film and history classes as well as volunteering at a local hospital and the local boys and girls club. Most importantly, I am also looking forward to spending more time with my wife, our four sons and our grandchildren, especially.
