Jennifer Tooker in the bullpen. Westport Republican readies a bid for governor.

Westport First Selectwoman Jennifer Tooker is preparing to seek the Republican nomination for governor, Daily Ructions has learned. Tooker has been a steady winner in vote-rich Fairfield County as fellow Republicans have been knocked over like ninepins since 2017.

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. No Republican has won a statewide Connecticut election since incumbent Jodi Rell’s historic 2006 victory for a full term as governor.

Tooker will face Erin Stewart, the Republican mayor of New Britain serving her sixth and final term. Stewart on Tuesday announced to a gathering of well wishers that she intends to explore a race for governor. The early going will be the contest to raise $350,000 in small donations. This is always harder than it looks and requires a high tolerance for drudgery. Stewart learned in 2018 how difficult it was to raise $250,000 in qualifying contributions that a candidate for governor needed that year. She made a convention eve switch to the race for lieutenant governor, losing the convention endorsement and primary to Southington Republican Joe Markley.

Former volunteer soccer coach Tooker enjoys a loyal cadre of supporters in Westport, a town thick with campaign givers. Her husband, Mo, is connected in state business circles, though it can be difficult to squeeze even a few bucks out of the state’s politically timid corporate community. The state’s University of Notre Dame graduates may also pony up for fellow alum Tooker.

Four of the state’s five most recent governors have been from Fairfield County.

Both Stewart and Tooker will need to steer clear of soliciting local contractors for campaign dough. Republican Matthew Corey, a frequent candidate for high office, is also considering joining the race for governor.

The first campaign finance reports are due in April. The math tells the tale, as does a candidate’s array of ideas to share at local party committee meetings, where the questions can be unexpectedly penetrating.

Published January 28, 2025.