By John Schwing

WESTPORT — Elections for town offices, among them the chief executive post of first selectman, are this year’s marquee political event.

There is, however, speculation that one of the expected contenders for the town’s top job — the current holder, First Selectwoman Jennifer Tooker — may instead have her eyes on a bigger prize: the governor’s office in 2026.

That, at least, is the topic of a post by state politics blogger Kevin Rennie, who in an item posted Wednesday in his “Daily Ructions” blog, states, Tooker “is preparing to seek the Republican nomination for governor.”

The post, which has no comments by Tooker or any other sources, alludes to her cross-over appeal, saying: “Tooker has held on in Westport as the once reliably Republican town has become a Democratic stronghold, demonstrating cross-party appeal that is essential for any Republican to have a chance in a statewide contest.”

Tooker, elected first selectwoman in 2021, won in a squeaker over Democratic state Rep. Jonathan Steinberg, 4,237 to 4,168. She succeeded fellow Republican Jim Marpe, having won a seat on the Board of Selectmen as his running mate in 2017. She previously was a member of the Boards of Education and Finance, the Conservation Commission and the Audit Subcommittee.

Tooker did not immediately respond to questions about her election plans from the Westport Journal on Wednesday morning.

(This article will be updated if she responds.)

Open field for first selectman’s office

If Tooker does decide to make a bid for the Republican nomination to run for governor next year, she presumably does not plan to seek re-election as first selectwoman this Nov. 4.

That development would spark a scramble in both major political parties to field contenders for the town’s top job.

Contender already in GOP race

Meanwhile, if Tooker seeks the GOP’s gubernatorial nod she would face a contender who has already made her intentions known.

Erin Stewart, the 37-year-old mayor of New Britain, on Tuesday announced she has launched an exploratory committee to start fundraising for a gubernatorial campaign.

“It’s a big day, because we’re kicking off the first leg of what could be an almost two-year journey to usher in a new generation of leadership to the state of Connecticut,” Stewart said at a press conference in New Britain City Hall, according to a report by the CTMirror.

Both Stewart and Tooker are considered “moderate” Republicans, an increasingly small faction of today’s Republican Party under the sway of newly re-elected President Donald Trump and his MAGA allies.

Tooker, for instance, has been a firm supporter of TEAM Westport, the town’s multi-cultural and diversity committee, while such DEI (diversity, equity, inclusion) initiatives have been slashed at the federal level since Trump and his appointees took office two weeks ago.

A more conservative contender is also expected to enter the field for the GOP’s gubernatorial nomination, such as Matthew Corey, according to Rennie, who is also a Hartford Courant columnist. Corey lost two contests, in 2024 and 2018, to U.S. Sen. Chris Murphy.

GOP standard-bearer will face long odds

The eventual Republican nomination faces steep odds against whoever the Democratic candidate is. No Republican has won statewide office since Jodi Rell won the governor’s race in 2006.

Gov. Ned Lamont, the incumbent Democrat, has not indicated whether he plans to run for a third term next year.

But in winning his 2022 re-election race, Lamont proved his appeal among suburban voters, such as those in Westport, where he overwhelmed Bob Stefanowski, the Republican standard-bearer, with 8,776 votes to 3,416.

If Lamont runs for re-election, he also has formidable personal wealth to self-fund his campaign. He spent $25.7 million on his 2022 election campaign, CTMirror reported.

Tooker, if she wants to qualify for Connecticut’s Citizens Election Program, a source of public funding for state candidates, initially would need to raise $350,000.

John Schwing, interim editor of the Westport Journal, has held senior editorial and writing posts at southwestern Connecticut media outlets for four decades. Learn more about us here.