CT Patch Candidate Profile: Win Smith, Jr. For Milford Board Of Aldermen

MILFORD, 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 candidates to answer questions about their campaigns and will be publishing candidate profiles as election day draws near.

Win Smith, Jr., a Republican, is a Milford resident running for Board of Aldermen.

Occupation:

attorney for 40 years

Family:
My wife is Debbie Franco Smith, for 43 years. We have 3 children, Catharine (39), Hannah (37), and Win III (35), who lives in Milford. We have two (2) grandchildren, Coco (7) and Lulu (2), who also live in Milford.

Previous public office, appointive or elective:

I have been a Milford Alderman for the last 2 years. I was the state Senator from Milford from 1993 until 2005, serving as assistant Majority Leader and a variety of other positions. I have also served as Milford's City Attorney, a Connecticut State Ethics Commissioner, and a Milford Police Commissioner.

Why are you seeking this office?
I became increasingly concerned about the nature and direction of our local government and became increasingly outspoken about my concerns. My friends and acquaintances challenged me to run for office, so I did. Having served for 2 years on the Board of Aldermen, I have realized that the problems are worse than I thought. The drift in our government is pronounced and powerful. Fiefdoms have developed and are staunchly defended. Dissent is actively and angerly discouraged and repressed. Special interests have a disproportionate influence on our policy making. The voice of the common man and woman is rarely heard and acted upon. There are related reasons but those are the core reasons.

The single most pressing issue facing my constituents is ____, and this is what I intend to do about it:
Taxes. Taxes. Taxes. I am one of only 2 member of the sitting Board of Aldermen (the other being Andrew Fowler in the 1st District) to vote against every tax increase that has come before us. I have argued strenuously against all these tax increases. The arguments appear to be getting heard. The last tax increase was voted through on an 8-7 vote, whereas the 1st tax increase was voted through on a 13-2 vote. The present Mayor offered a series of amendments to eliminate the most recent tax increase and those too were voted down on an 8-7 straight line party vote. I will not give up this struggle against tax increases. And this struggle requires that stands be taken against spending and bonding increases when the same come before the Aldermen. The standard for any such spending increases need to be greater than "that is the way we have always done it", or "that is what is being asked for". Those are excuses, not reasons. Spending taxpayers' money demands far better reasons, in my view. And it takes backbone to stand up to the constant requests for increased spending. THAT is why I am running again.

What are the major differences between you and the other candidates seeking this post?
See my answer in #13 above. Having voted consistently against the "go along to get along" mentality, I will continue to do so. Almost all of the rest of the Alderman who are running for re-election (with the exception of Andrew Fowler), just want to vote so no one will be upset with them, or reasons similar to that. I stand up for the common taxpayer and say "no" to all these spending and bonding requests, and all these tax increases. That is the PRIMARY difference between me and almost every other incumbent Alderman seeking re-election. You can count on me to stand up for you, even when no one is watching. And let me tell you, that is rare in politics.

What other issues do you intend to address during your campaign?
Bonding, density of development in Milford (way too much development crammed into way too small spaces), and local control (our present Aldermanic board has been way to compliant in turning over/conceding our authority and control to other levels of government and/or bureaucrats; that is wrong, I have consistently voted against that (sometimes alone on this Board) and I will continue to do so).

What accomplishments in your past would you cite as evidence you can handle this job?
I would refer to my answers in the previous questions. My record in the past 2 years is clear. I will continue to lead the fight against tax increases (alone, if need be), unwarranted bonding (again, alone if need be (my record shows that that is exactly what I have done), and local control (ditto). I would also note that few, if any of the present Board of Aldermen, actually read the contracts, agreements and "memoranda of understandings" that come before us. They are more than willing to let someone tell us what the documents say rather than reading the documents for themselves, coming up with their own questions and conclusions and then challenging the proponent of the matter. I have shown a consistent willingness to challenge proponents of matters and force them to explain the proposal and, if they cannot defend the proposal adequately, to vote against it. There is a stunning lack of desire to do this. I will continue this effort to force proponents to justify what they are doing.

What is the best advice anyone ever gave you?
Marry the woman you love (which I did 43 years ago to Debbie Franco). It was far and away the best decision I ever made.

Is there anything else you would like voters to know about yourself and your positions?
My family has been in Milford since 1640. I am proud of that fact. My Irish ancestors came here around 1900. I was born and raised here. I went through the Milford Public Schools (MHS Class of '76). This is my home. I live here. We raised our 3 children here. My grandchildren live here. I care deeply about this community, its past and its future. Public service has always been important to my family. My father served in the legislature (I actually served in the same seat that my father had held 20 years earlier), and my family has held a series of leadership and other positions in the First Church, St. Mary's Church (I am a lector), the Milford Rotary Club (6 family members (including myself) have served as Presidents over the last 100 years), the Milford Red Cross, the Masonic Lodge, the Boy Scouts of America (my grandfather ("Pink" Smith) was the 1st Eagle Scout in Milford and at least seven family members (including myself) are Eagle Scouts). My family has run multiple businesses here in Milford, including the Smith Funeral Home, Smith Insurance and George J. Smith Real Estate. My own law office is here in Milford on the Green. We have 7 lawyers (including my son, Win III) and six (6) support staff. In short, Milford means a lot us and me. My family and I are dug in deep here. We are proud to call Milford our home. We will fight for Milford to have the brightest future that it can. And you can count on that.