Former MLB Manager Valentine Runs for Mayor in Hometown

Former Major League Baseball manager and player Bobby Valentine scoffs at any suggestion he might be out of his league running for mayor in his hometown of Stamford, Connecticut’s second-largest and fastest-growing city.

The 71-year-old rookie mayoral candidate rattled off a list of accomplishments, from his years managing baseball in the MLB and Japan to owning a chain of restaurants 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.”

With the Nov. 2 general election looming, the former Republican who submitted 188 signatures to get on the ballot as an unaffiliated candidate finds himself in a closely watched, competitive race against Caroline Simmons, a 35-year-old Harvard-educated state representative who already upset the shoreline city’s two-term mayor in the Democratic primary in September.

The race has attracted national attention, with former Republican President George W. Bush, who was a managing partner of the Texas Rangers when the team fired Valentine as its manager, contributing $500 to the former skipper. Simmons, whose campaign has received contributions from famous performers such as Michael Douglas and Bette Midler, was endorsed by former Democratic President Barack Obama.

Valentine, who managed the New York Mets, Boston Red Sox and the Japanese Pacific League’s Chiba Lotte Marines during his career, has outpaced Simmons in campaign fundraising, amassing more than $520,000, compared with nearly $430,000 she raised as of this month. Each has received endorsements from organized labor in a city where Democrats outnumber Republicans by more than 2 to 1. The maintenance and service workers and local firefighters are backing Simmons while the city’s teachers and police unions have endorsed Valentine.

The Republican candidate in the race, a former city police officer, withdrew last month and is backing Valentine.

The race has gotten testy at times, with Simmons accusing Valentine of “abandoning” the city when he was the public safety director and left town before Hurricane Irene hit in 2011 to broadcast a baseball game in Texas. He shot back that Simmons would have known it was “one of the most safe situations that ever occurred” if she had been in the city — a dig at her for having moved to Stamford in 2013.

Simmons, who grew up in Greenwich, Connecticut, co-chairs the General Assembly’s Commerce Committee and works at Yale University on maternal mental health policy. She previously worked 4 1/2 years at the U.S. Department of Homeland Security on domestic and international terrorism issues, traveling to Afghanistan multiple times.

She says Stamford voters want someone with her background 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.”

A surge of newcomers, especially New Yorkers who moved to Stamford during the height of the pandemic, has brought benefits and complications to a city of more than 135,000 where soaring property values have exacerbated a dearth of affordable housing.

The Rev. Winton Hill, a longtime Stamford resident and former pastor of Bethel AME Church, said Simmons has articulated a vision for the city more clearly than Valentine, who seems to be “just an individual celebrity running for office.” Hill, after attending last week’s final mayoral debate, acknowledged Valentine’s appeal but said he’s 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 he’s “not an ordinary old white guy.” He points to his time as a team manager living in Japan and as a young player living in the Dominican Republic and Venezuela.

“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, a retiree who lives in Stamford, said she hasn’t decided which candidate to support on Election Day. While she’s always voted Democratic, Berkoff said she might end up voting for Valentine because of his varied experience, on and off the baseball 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.”