It’s been 3 years since Jen Tooker was elected 1st Selectwoman.
Exactly 3/4 of the way through her term, now is a great time to welcome her back to “06880: The Podcast.”
Last week, she stopped by the Westport Library to chat. Our conversation ranged from the general (what’s surprised you about the job? what have you learned about the town? what are the challenges?) to the specifics: the capital plan (and how to pay for it), affordable housing (and where it will be built), and of course traffic (what can we do about it?).
Click below to hear the town’s top elected official talk about what’s on the top of her mind.

Hmmm… no comments? That’s odd.
Now, Jack, there’s 14 comments and, notably, there is not a SINGLE laudatory one…just sayin’
I thought I’d read your wash/rinse/repeat post crying because the FSW doesn’t reply to your emails
I mean, I can’t imagine why?
I can’t imagine why there are only two comments concerning her interview. Other posts have 30 and 40 comments. I wonder if one can read anything into that?
Victoria, It’s getting lonely here. It’s just me and you. Where do you live in Westport? I’m thinking of coming to Westport Saturday night. If I actually come up, I might invite Dan to the Spotted Horse for dinner and leave the invitation open to anyone. You’ll be invited too.
Well Victoria, DWJ? “Dinner With Jack?” Of course that’s if I come up, although my wife definitely is! Maybe both Dans will be there, and Eric and Scooter and anyone else who wants to come! I could even bring my home movies of Westport from 1941. I think this may be my 5th comment.
Here’s a comment.. we need new leadership in Westport. Photo op’s don’t get things done
Peter, I have an idea. If I come up on Saturday, why don’t I write an e-mail to Ms Tooker and ask her to meet us at the Spotted Horse for dinner? You can bring your camera too. They have great food there too. F.O.T.I.- Feast On The Ingredientes. I’ll write that e-mail!
The lack of comments is odd. She has been utterly useless.
One more year and we’ll be done with her forever. And we hopefully won’t endure much ongoing damage (like the loss of the Community Gardens or much of Jesup Green).
I have not met our First Selectwoman and not really followed her policies. My wife has and says she is a nice person. That said, I spent 30 years in Texas politics including deputy manager for Anne Richards in ’94. And one thing I learned through that exposure was never trust a Dallas Conservative, which Ms. Tooker is. We need a professional city manager in the town to curtail or at least tame some of our radical transformation.
Scooter, Westport has an operations director. His name is Tom Kiely. He’s a good guy actually. I assume he takes care of the daily nuts and bolts stuff. And Ms. Tooker BTW it’s Compo Beach Rd. Not S.Compo Rd.
Thank you Dave. But it seems Mr. Kiely’s major experience is a being a cop despite his degree. Look up Professor Woog’s story on Tim Honey (Staples ’64) who was a true professional city manager.
Will Do Scooter. Tim Honey was a good friend of my brother, Jay. Also Staples ’64…
As was my brother, Duff. Nothing against Mr. Kiely but crime is not one of the many problems facing this town at the present.
Tooker, the most visible Republican in town, has said not a word about Trump’s danger, hateful words or lies…she must be assumed, therefore, to be voting for him. Thus she can’t be worth the cloth in her dress.
Dan (Katz, not Woog) You and Jack have TDS (Tooker, not Trump) Derangement Syndrome. Dan is dreaming of Tooker (without her dress) and Jack is dreaming of Tooker (without FOTI). It’ll never happen fellas. Besides, Tooker still has a year left to MWGA (Make Westport Grout Again). Go to the polls and vote for a real woman.
Great comment, Eric…however, PLEASE keep the dress ON said subject…PLEASE.
Dan, U DA MAN!!!! (U2 Jack) Make Westport Grout Again!!!
I enjoyed the interview. Very informative. Well done Dan and Jen.
I have two comments left (if you include this one). Anybody want 2 buy them?