Jennifer Tooker Makes a Case for Westport First Selectwoman

Westport Selectwoman Jennifer Tooker, a Republican, is running for the job of First Selectwoman, facing off against Democratic State Rep. Jonathan Steinberg for the open seat.

Incumbent First Selectman Jim Marpe, who was first elected in 2013 and most recently won reelection in 2017 with 50 percent of the vote, compared to his Democratic opponent’s 45 percent, is not seeking reelection.

The Connecticut Examiner spoke with Tooker about her campaign and priorities if elected. 

This interview has been edited for clarity.

What inspired you to run for First Selectman of Westport? 

My husband and I moved to Westport 13 years ago, and we both worked in the financial services business, and landed in Westport because the global headquarters of the company we were working for was in Stamford. We knew this would be home for a while, and I’d always wanted to get involved in local government. Within six months of arriving, I joined the conservation commission, and through serving on that commission, I got even more interested in how local government worked. I really saw how the decisions we made affected people’s lives around us. I ran for the Board of Education, won a seat, then ran and won a seat on the Board on Finance, and then ran and won a seat as second selectman alongside Jim Marpe. I couldn’t think of a better way to serve the town. 

To what extent would you want your administration to follow in Jim Marpe’s footsteps? 

I am incredibly proud of the Marpe-Tooker administration and all we’ve accomplished, making long term investments in Westport infrastructure, following a financially conservative annual budget process, and doing all of this with a flat mill rate. I couldn’t be more proud of the way we’ve managed this town, especially through a once-in-a-lifetime global pandemic. In this area of Connecticut, our town had the most net new residents move in out of all surrounding towns. We have a 90 percent occupancy rate on main street, and our local economy is absolutely booming. Jim and I are incredibly similar in our backgrounds, because we both come from senior and executive management positions in financial services. I do think the key to our success is that we do have that management background, which is going to be incredibly important going forward for continued future success in Westport.

Are there any ways in which you would lead Westport differently, or should voters think of this as voting for another term of the Marpe-Tooker administration?  

In leadership and management style, we are very similar, and that’s been key to why the town is run so well. I will say that there is nothing like a global pandemic to potentially change some priorities. We’re not going back to 2019, and our residents have made some lifestyle changes during the pandemic that I think are going to stick around for a while. 

One of the most obvious for us is that I don’t think people are going to go back to commuting five days a week. A large portion of Westport does commute, and this means more people working from home on a more regular basis. That means more people using our beautiful parks and beaches, because they couldn’t before when they were working 14 hours a day. It means more people interacting with our local businesses running out to lunch on a Tuesday where before, they were in New York. Our administration is going to stay very focused on what our town needs to do to pivot to support those. 

I think there will be priorities that will be important for us going forward that probably weren’t priorities back in 2019, like dealing with sidewalk repairs, increased usage of amenities, and increased pedestrian traffic, as well as internet and broadband. We are also a coastal community and also have a tidal river running through the center of town. I don’t have to tell any resident of Connecticut that we are having more frequent and more intense storms. We need to focus our work on infrastructure resiliency when it comes to being able to handle the types of storms that we’ve been seeing more frequently in the last five to ten years. 

Do you see a world where, if you were first selectman, Westport residents might see a raise in local taxes? 

You never say never, but I would say that a consistent mill rate is really the important piece to me. Our steady mill rate continues to be an important piece of what makes our community so interesting from a real estate investment standpoint. My approach will be to start our budget season thinking that we don’t want to raise taxes, and we’ll work backwards from that to figure out how to continue to deliver superior services and make long term capital upgrades without raising the mill rate. 

We’ve done a lot of infrastructure upgrades over the last four to eight years while keeping the mill rate steady, and the secret to our success is that we have a really good balance between commercial and residential tax dollars as part of our grand list. It’s really important to continue to look at and make sure we’re cognizant of that balance so we can continue to be a great place to grow a business. 

What sets you apart from your opponent?

My management and leadership background really is the differentiator between myself and my opponent. I not only have a private sector background in senior management, but in town government. I’ve been in roles where you’re making decisions you need to be held accountable to execute, and that is the fundamental difference between being the chief elected officer of town versus maybe some other roles in government. Westport does not have a professional town manager, so when electing a first selectman, the town is really electing the top leader and operational manager of the town. 

What are some examples of things you’ve taken the lead on as second selectman? 

A big piece of what I’ve worked on in the last four years has been getting to know the local business community and ensuring the administration was responsive to their needs. In the work that I did before the pandemic, those were the days when there were tumbleweeds going down main street, and we did have some commercial real estate occupancy issues in town. I worked very closely with the local business community to ensure that they had a voice in the administration, and that we understood why Westport was the place they chose for their businesses. 

I think that work set us up very well for navigating the pandemic, and I led, as part of the administration, the reopening of the local economy after the shutdown. I made sure that the way we reopened the economy supported them and helped our residents feel safe. As a result, we now have a booming local economy, and I’m really proud of the work I’ve done to make that happen over the last four years. 

Also, before the pandemic, I was instrumental in setting up Westport Together, an alliance between the town and schools and parent-teacher association and any nonprofit in town that does programming focused on the health and well-being of children and families. I was so grateful to have this platform in place pre-pandemic, because as you can imagine, we have been churning out programs and information pretty aggressively for the past 18 months. 

We also launched a website, Facebook page and Instagram account flush with current information around resources and support for all sorts of different social-emotional health and well-being issues. None of that existed before, because the nonprofits, the town, and even the parent-teacher association was putting out their own stuff. Now, they’ve been able to consolidate and combine email distribution lists, which is getting information in front of residents in a more comprehensive way. Our flagship launch was a series on how to raise an adult, and we drew crowds of a couple of hundred parents over multiple different sessions wanting to know more about how to support kids’ goals without adding to their anxiety. 

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