Bobby Valentine, a former Major League Baseball player, and manager laughs at the suggestion that he may be running for mayor of Stamford in Connecticut’s second-largest and fastest-growing municipality.

The 71-year-old rookie mayoral candidate listed a number of achievements, including his time managing baseball in Japan and MLB to owning a restaurant chain and serving as Stamford’s public safety director.

“I have passion for this city. I have a skill set that meets the requirements of leadership, management, of team building,” Valentine said in an interview. “I mean, I would think if there was a job description out there for a mayor, those things would be in it.”

The Nov. 2 general elections are fast approaching and the former Republican, who submitted 188 signatures in order to be on the ballot as an independent candidate, finds himself in a competitive race against Caroline Simmons. Simmons is a Harvard-educated state representative, 35, who upset the two-term mayor of the shoreline city in September’s Democratic primary.

This race attracted national attention. Former Republican President George W. Bush was a managing partner in the Texas Rangers when Valentine was fired as its manager. He contributed $500 to the former skipper. Former Democratic President Barack Obama endorsed Simmons’ campaign, which has attracted contributions from stars like Michael Douglas and Bette Midler.

Valentine, who oversaw the New York Mets, Boston Red Sox, and the Japanese Pacific League’s Chiba Lotte Marines in his career, outperformed Simmons in campaign fundraising. He raised more than $520,000 compared to the nearly $430,000 she raised this month. In a city where Democrats are more than two to one, each candidate has been supported by organized labor. Simmons is being supported by local maintenance and service workers, firefighters, and police unions. Valentine has been endorsed by the city’s teachers.

The Republican candidate for the race, an ex-city police officer, withdrew last week and now supports Valentine.

Simmons has accused Valentine of abandoning the city in his capacity as public safety director. He left the city in 2011, to broadcast a Texas baseball game. This has caused some heated exchanges between the two races. He retorted that Simmons would have known that it was “one the most dangerous situations that ever happened” if he had been there — an attack on her for moving to Stamford in 2013.

Simmons, who was born in Greenwich Connecticut, is co-chair of the General Assembly’s Commerce Committee. She also works at Yale University to address maternal mental health policy. She spent 4 1/2 years previously at the U.S. Department of Homeland Security, where she worked on domestic and international terrorist issues. She also traveled to Afghanistan several times.

She believes Stamford voters need someone with her past who is “ready on day one.”

“They have appreciated our message of wanting to make our city work better for people,” Simmons said of voters in an interview. “And I think people recognize that he may be a great baseball player and have that celebrity status, but they don’t necessarily want him as mayor or don’t think that translates into being a good mayor.”

The influx of New Yorkers, particularly New Yorkers, who came to Stamford at the height of the pandemic has created both benefits and problems for a city of over 135,000. However, soaring property prices have made it difficult to find affordable housing.

The Rev. Winton Hill, a Stamford resident for many years and former pastor at Bethel AME Church said Simmons has communicated a vision better than Valentine. Hill attended last week’s final mayoral debate and acknowledged Valentine’s appeal, but stated that he is someone who represents the past.

“He’s an older white male who’s been very successful in life and whose personality is charismatic, and (Simmons is) a young lady who still has a lot to learn, but has a whole life in front of her and who is much more representative of the future,” said Hill, who is 73. “And so, my gut feeling is to invest in the future.”

Valentine insists that he is “not an average old white guy.” He points out his time in Japan as a team manager and in Venezuela as a young player.

“There’s no chance of a 35-year-old girl who grew up in a private setting, going to a private school in Greenwich, Connecticut, could possibly relate to the diverse culture of Stamford, Connecticut, better than I do, no matter what the age is,” he said. “It’s an absolute impossibility in my mind.”

Linda Berkoff is a retired woman who lives in Stamford. She said that she hasn’t yet decided which candidate she will support for Election Day. Berkoff, a retired woman who voted Democratic all her life, said that she may vote for Valentine due to his diverse experience on and off the field.

“He seems to have enough history in managing things … and to me, that makes a difference,” she said. “I’m really interested in someone who will manage the city without going to one side or the other. … Think of all of us. You’re not a Democrat or you’re not a Republican. You’re the leader of Stamford. You’re the manager.”