By John Schwing
WESTPORT — One of First Selectwoman Jennifer Tooker’s rivals for next year’s Republican gubernatorial nomination claims to have the support of the party’s kingmaker, President Donald Trump.
Stewart, the 38-year-old, six-term mayor of New Britain, reportedly told a meeting of the Republican State Central Committee on Thursday, “We are going to get endorsed by President Trump,” according to the “Daily Ructions” state politics blog by Kevin Rennie. In January, Rennie also was the first to report Tooker’s planned pursuit of the GOP nod for governor in 2026.
Stewart flips on “Trump is a flop”
Stewart said the anticipated endorsement, according to Rennie’s report, will be “great,” adding that she would not “allow the left into thinking, believing that is a bad thing for us. That that is going to lead to us not being able to be successful.”
That assertion is contradicted by Trump’s dismal electoral record in Connecticut.
In his three campaigns for president, Trump has been roundly rejected by state voters in favor of Democrats Hillary Clinton, Joe Biden and Kamala Harris.
Stewart, in fact, took a diametrically opposed stance in 2018 when she made a brief, unsuccessful bid for the GOP gubernatorial nod, and after switching to seek the nomination for lieutenant governor, was defeated in a primary.
“Anybody who is coming out with the ‘Go Trump!’ sign is not going to win the hearts of Connecticut voters, for sure,” Stewart said in a 2018 CT Mirror report. “Look how badly he lost the state. That’s a fact.”
Tooker appears to be trying to have it both ways when asked about the sharply divisive president. In interviews with out-of-town media outlets since she declared her candidacy, Tooker has given the same answer about Trump each time — she agrees with him on some issues and disagrees with him on others.
“Moderates” typically not to Trump’s taste
Stewart, like Tooker, has a moderate record on social issues, an increasingly rare breed of candidate in the MAGA dominant, aggressively conservative GOP under Trump’s leadership.
Tooker has been a firm supporter of TEAM Westport, the town’s multi-cultural and diversity committee, while DEI (diversity, equity, inclusion) initiatives have been slashed at the federal level since Trump and his appointees took office, compounded by additional threats to cut aid to state and local governments that continue DEI policies.
She also refused to support the Board of Education candidacy of outspoken conservative and fellow Republican Camilo Riano when he ran for the Board of Education in 2023.
Neither Stewart nor Tooker is the kind of candidate who traditionally wins Trump’s blessing. In terms of ideology, two lesser known potential candidates are much more closely aligned with the president — Matthew Corey, who lost in a landslide to incumbent Democratic U.S. Sen. Chris Murphy last November, and Peter Lumaj, who has sought the GOP’s backing for several statewide offices in the last decade.
Despite Trump being strongly rejected by Connecticut’s general electorate, the Trump brand still carries significant weight among hard-core GOP activists. In 2022, for instance, his late endorsement of Leora Levy propelled the first-time candidate from Greenwich to a primary win over the GOP state House leader Themis Klarides, who had the state party’s backing for the U.S. Senate nomination.
If Trump does support Stewart’s candidacy, it would be a steep hurdle for Tooker to overcome.
Stewart amassing bigger war chest
Another early hurdle for Tooker is the large gap in fundraising between her campaign and Stewart’s, which officially is an “exploratory” committee since the New Britain mayor has yet to formally declare her candidacy.
Stewart, according to her Facebook page, raised $132,668 in 63 days so far this year, while Tooker collected roughly half that amount at $66,182 from March 6-31, according to a post on her “tooker4ctgov” Instagram page.
That gives Stewart a big advantage in gaining access to financing under the state’s Citizens Election Program, which sets a $350,000 threshold before qualifying for support.
Nonetheless, Tooker said she is “extremely grateful” to donors, and said in her Instagram post that her “incredible” fundraising so far “shows without a doubt that the people of this state are craving something new and something better.”
John Schwing, consulting 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.
And so it begins.
As our first selectwoman focuses on fundraising for her gubernatorial campaign, who is running the town at this critical juncture of a $100 million school project, a ridiculously supersized Hamlet development, lagging progress on our Longshore and Parks and Recreation master plans, and acrimony among merchants on a viable downtown parking plan …. shall I go on?
I bumped into a longstanding state-level GOP elected official today (4/12/25), who opined that Tooker was assured defeat on a second term in Westport, so running for governor was a way to save face. I don’t know, but I sure am glad we’ll have a better choice for Westport this fall.
Westport citizens need to step up and pay attention to town matters these next few months of lame-duck leadership.
And now we know (from the State) that FS Tooker was told about the plans around Post & Sherwood (where the clear-cutting has occurred) and did nothing to step in and offer any concerns about the impact on the neighbors (or let the neighborhood know).
She’s doing her own Oppo.
RINO Tooker will never win a primary in the Republican Party.
Not even in Westport, where registered Republicans overwhelmingly voted for the true Republican principles that I represented in the 2023 race for the Board of Education.
If her interest in running for CT Governor is just an excuse not to face the local electorate, she would do better running as an Independent. She might get some Democrat votes, plus the vote of fellow RINO, Robert Harrington.