CT Patch Candidate Profile: Brian Gaines for Board of Finance

WESTPORT, CT — The 2025 election is heating up in Connecticut and there are plenty of races with candidates eager to serve in elected office.

Connecticut Patch asked local candidates to answer questions about their campaigns and will be publishing candidate profiles as election day draws near.

Candidate's Name:
Brian Gaines

What office are you seeking?
Board of Finance

What town do you live in?
Westport

Party Affiliation:
Republican

Occupation:
Hedge fund manager (23 years)

Family:
Married to Rebecca, Daughters Alexandra (18) and Liv (16) and stepsons William (17) and Sawyer (14)

Does anyone in your family work in politics or government?
No

Previous public office, appointive or elective:
No

Why are you seeking this office?
I’ve lived in Westport for nearly 18 years, and I want to give back to the town that has given so much to my family. With nearly three decades of experience in finance, I believe I can make the greatest impact on the Board of Finance. It’s the place where my professional background aligns directly with the town’s needs — ensuring we make smart investments in our community while maintaining fiscal discipline.

The single most pressing issue facing my constituents is ____, and this is what I intend to do about it:
The single most pressing issue facing my constituents is ensuring Westport remains both financially competitive and highly desirable as a place to live. I intend to address this by keeping our tax rates in check, making smart investments in schools, infrastructure, and public safety, and scrutinizing unnecessary expenses so that every dollar goes toward strengthening the town’s future.

What are the major differences between you and the other candidates seeking this post?
Fortunately for Westport, I believe all the candidates for the Board of Finance are highly qualified and committed to serving our community. Since I am running unopposed, I see my role less in terms of differences and more in terms of responsibility — to use my financial background to support sound budgeting, keep taxes competitive, and ensure resources are directed where they benefit residents most.

What other issues do you intend to address during your campaign?
Because I am running unopposed, I view this campaign less as a contest of issues and more as an opportunity to share how I hope to contribute on the Board of Finance.

What accomplishments in your past would you cite as evidence you can handle this job?
I’ve spent nearly 30 years analyzing companies and making investment decisions based on risks and rewards. That experience translates directly to the work of the Board of Finance, where the goal is to make prudent financial choices that balance fiscal responsibility with the needs of the community.

What is the best advice anyone ever gave you?
Life and success is mostly about getting back up after you fall. Setbacks happen to everyone but the willingness to learn and move forward is what's important.

Is there anything else you would like voters to know about yourself and your positions?
I’m excited to get involved and do my part to help Westport continue to be an outstanding place to live.