
By Thane Grauel
WESTPORT — After more than a decade devoted to public service, Jennifer Tooker ascends to the pinnacle of town government when she is sworn in Monday as the town’s first selectwoman.
Before getting involved in Westport government, Tooker had a successful career in insurance, here and abroad. Westport has been home since 2008 to Tooker’s family, including husband Mo and their three children.
Tooker’s public service has included stints on the Board of Finance, Board of Education and Conservation Commission. And, for the last four years, she has been second selectwoman, elected to that post as the running mate of First Selectman Jim Marpe, the fellow Republican who she is succeeding.
Historic hallmarks
When Tooker is inaugurated Monday — the swearing-in ceremony is set for 7:30 p.m. in Town Hall — she becomes the first Republican woman to be the town’s chief executive officer. And with running mate Andrea Moore, they will be the first two women from the same political party to comprise the Board of Selectmen’s majority.
Their Republican team appeared to have an initial disadvantage in the Nov. 2 election, at least according the voter enrollment data. Westport Democrats outnumber Republicans more than two to one, plus there are nearly as many unaffiliated voters as Democrats.
Narrow victory triggers “overwhelming emotion”

In a post-election interview with the Westport Journal, Tooker did not take her victory in stride.
“These voters are very savvy,” she said of Westporters. “To have won the respect and the support of over 50 percent of the people was a big deal. I’m really honored.”
The margin of victory Nov. 2 — 69 votes — over Democrat Jonathan Steinberg was slim, but exciting.
“There is nothing like the adrenaline associated with an election,” Tooker said. “It really is an overwhelming emotion. It is.”
“You stand there and you think, all these people who have really sacrificed a lot over the last couple months, supporting you, talking about you, endorsing you, really believing in you,” she said.
“The enormity of that is pretty overwhelming,” she said. “So, you really want to do right for your supporters, for everybody.”

Getting to work, setting priorities
Tuesday morning, Tooker begins work. That’ll mean turning campaign talking points into action.
Among her goals is forming a local commission to address the growing traffic problems on local roads. The group would consist of people from affected neighborhoods and town experts. Many of the problem areas involve state roads and river crossings, which means that getting cooperation from the state will be crucial.
A master plan for Longshore Park is another priority, Tooker said, as is continuing the rebound of downtown Westport, and supporting the businesses in Saugatuck and elsewhere in town.
Tooker will be working with town departments, elected bodies and volunteer entities. Some communities have trouble filling volunteer positions, but Westport has no shortage of talented people willing to share their expertise.
Why?
“I think because they care,” Tooker said. “They genuinely care about making their community a little bit better tomorrow than it was yesterday.”
Asked about the town’s boards and commissions having a tradition of acting in a non-partisan manner, Tooker noted that agency chairmen from one political party have generally appointed vice chairs from another party.
“I can’t remember a vote, on a board or commission, at least not in my recent memory, that goes on party lines,” Tooker said. “We don’t seem to govern that way in Westport.”
Family supportive of new role
Is her family up for this?
“Too late now,” she said with a laugh, but added yes.
“We absolutely had a series of family discussions prior to me wanting to get the endorsement of my party, prior to me putting my name in the hat,” she said. “To really make sure everybody really felt good about this, not only the campaign process, but once you’re in office, the attention it can attract, and the long nights, the long days.”
“I’ve always been a working mom, so that piece isn’t a surprise … but then again, there is something a little bit different with your mom being the top elected official in town,” she said.
“The family has been 150 percent supportive of me.”
And there’s one other goal:
“I’d like to get a good night’s sleep before starting on the 16th.”



The first “right thing” she ought to do is to follow the law and direct the Third Selectman seat to be filled by TJ Elgin. He was the only other person who ran as First Selectman. He ran as a candidate for a different party, libertarian.
The position does not belong to the democrat party. The law expressly provides that the position belongs to a person who ran as a candidate for that office. No one has any duly authorized appointment powers right now. It would be nice if the Third Selectman position is filled by operation of law, not what democrats or even Jen Tooker thinks they would like the law to be. The fact that our town attorney provides legal guidance, a registered democrat who served as Steinberg’s former campaign manager, only adds yet another deep wrinkle to this potential lawsuit against our town.
The town’s time and resources should be expended in a different and more constructive direction.
We must be very vigilant in keeping Republicans in check, including the two cardboard cutouts that are going to be in Town Hall as of today. Republicans are totally focused on taking over this country, creating one religion, denying the right to vote to a large segment of our citizens, and becoming a cult-like organization. We are witnessing the beginning of a Fascist takeover in the US and we must do everything we can to stop that from happening. Awareness is where we begin.
too much coffee this AM?
Rozanne: How impossibly deluded can one person be? Liberals control just about every form of media in this country, from the TV networks to social media and major newspapers. They are also in control of the house and have a voting majority in the Senate, with Harris. And with that control, Democrats have– in 9 short months– almost singlehandedly destroyed every facet of our country. From inflation at 30-year highs (not an accident), to gasoline prices up 100%, to the southern border crisis where drug cartels and child trafficking are back in business. Fentanyl and opioids pouring over the open border, resulting in the death of 100,000 Americans over the last 12 months. The supply chain disruptions that have resulted in shortages and empty supermarket shelves– wait until rationing starts, that will happen shortly. To the Afghanistan withdrawal, in which we handed over multiple billions in high tech military equipment to the Taliban, stranded many Americans and released the terrorist that killed 13 American service members. To CRT, which is being introduced in K-12 curricula across the country. Yes, it is happening. The NEA has officially endorsed it. To the violence that is skyrocketing not just in major cities, but in every town in America– thanks to the insane “defund the police” movement from progressives. I could go on with a dozen more examples of how the Biden administration– with the backing of a compliant media– is destroying our country one day at a time. The fact is, the world’s largest social media platforms take direction from the Biden administration in choosing what to amplify and what to suppress or remove. This is the union of corporate and state power, one of the classic hallmarks of fascism. Get a clue please.
Rozanne Gates, I’m not sure what you said about Republicans is a bad joke, or if you are serious.
May I make a suggestion:
Stop watching the Fake News and turn on the real news stations FOX NEWS and you will understand
what party in trying to turn America into a Socialist country.
Sincerely,
Gerald F. Romano, Jr.
Rozanne, as always Republicans like myself who have always, and will always support the “values of all people” always appreciate your “Trumpism” comments. Wishing you a great day and hopefully a “stress free” next 4 years in Westport as Jen Tooker will lead and work for “ALL Westporters” like Jim Marpe did over the previous 8 years. I have an idea for you, why don’t you put some pressure on our Democratic Representatives up in Hartford to start prioritizing the needs of Westport instead of the Democratic machine that runs CT?
Roxanne, I know that I and others are not going to convince you to change your mind, but unless responsible citizens moderate comments, we all risk more polarization. Having served Westport for 20 years as a member of the Republican party, I can tell you there were no instances where I thought, “Oh what is the national republican policy on X” before voting or commenting. I know memory fades over time, but a majority of Westport Republicans did not vote for Donald Trump in the primary prior to his election, they voted for John Kasich.
Why did the Westport Republican Town Committee donate $286.15 to the Trump Make American Great Again Committee on August 27, 2020? It’s right there in the election-finance databases. Did you guys have a bake sale or something? Did one member of the RTC make this donation without the rest of the committee knowing? It’s not a good look. Until this is explained, I’ll vote for the party that supports people of color, people who aren’t con men, and books.
Tom Prince: “I’ll vote for the party that supports people of color”?? lol. Why are Democrats consistently in favor of shutting down charter schools– something that is overwhelmingly supported by blacks and latinos? Have you bothered to look at the destructive legacy of LBJ’s The Great Society and what that did to the black family unit? Probably the single most destructive piece of legislation for African Americans in US history. Two parent households among blacks is now around 30%, down from 70-75% pre The Great Society. Is defunding the police a good idea? How about open borders? Or the war against traditional marriage? How about the plight of blacks in urban America today? Crime is skyrocketing due to the defund police movements. Democrats have had control of most major cities for decades, and the record speaks for itself– incredibly high crime rates (Chicago!), awful public schools, where a small percentage graduate and those that do are basically illiterate. You think that Democrats– who support all of this– really care about “people of color”? Think again. Thankfully African Americans are finally starting to wake up and realize that Democrats only care about their vote.
Scared Anonymous Person: Sit back with some Tito’s. Tucker’s on soon!
Nice comeback…not. “Scared”? lol. But Art Leftko gets it. It is sad that I live in the same town as people as disconnected from reality as you appear to be. Do enjoy the Tito’s though, thanks!
Rozanne, what is most frightening about your delusional screed is that a large chunk of Westport likely shares your opinions. Democrats are the ones who have created this Republican bogeyman in order to justify their own extreme policies. You clearly have no concept of what Fascism is. I’m fairly confident the road to perdition does not begin with Jen Tooker. It is somewhat frightening to me that I shop in the same grocery stores and drive on the same roads as people as disconnected from reality and inflamed with misdirected emotion as you appear to be. People like you are causing me to lose faith in this country. We will get the leaders we deserve.
Roxanne:
Don’t you think that referring to Jen and Andrea as cardboard cutouts is unnecessarily disparaging? Both are proven intelligent and articulate accomplished women in their own right, and volunteering to serve our Town is extraordinarily commendable. At least give them an opportunity to lead, address problems, and engage with the community as they intend to do from day one.
And providing them your support will go much further than unwarranted premature criticism.
Dr J
Roseanne, you hate trump, but why do you act like him? Always taking to the internet, calling people out from behind your keyboard, spewing divisive comments from your contaminated far political views that are everything your party apparently calls out and campaigns on, “diversity, equity inclusion,” and “hate has no home here.”
I do not let your opinions and words represent Democrats. In fact, my friends who are Democrats and republicans are great people and they get along. Except you.
Well, hate has no home in Westport. Leave and take your hate with you. Your attitude and approach is what’s the problem today. And what we try to not teach our kids.
“Leave and take your hate with you.” Did you just banish someone for expressing an opinion? How long does she have? Until sundown?