The mayor’s race in Stamford has been flooded with money and intrigue, thanks largely to the flamboyant presence of Bobby Valentine, a first-time candidate and former Mets and Red Sox manager.In Stamford, the second-largest city in Connecticut, a province of mixed baseball loyalties lying between New York and Boston, one of the last remaining names on the ballot for mayor this fall is more familiar to sports fans than to municipal policy wonks: Bobby Valentine.It’s a name that needs little introduction in this city of 135,000 people, which has emerged from its 20th-century role as a financial services exurb to become a magnet for apartment developers and tech companies. All through Stamford, lawns and traffic islands are carpeted with the campaign signs of Mr. Valentine, who managed the New York Mets from 1996 to 2002, including a World Series loss to the Yankees, and lasted one tumultuous season as the skipper of the Boston Red Sox.That Bobby Valentine, the former ESPN commentator whose managerial career took him from the employ of George W. Bush with the Texas Rangers to the Chiba Lotte Marines in Japan. And yes, the same Bobby Valentine who once disguised himself with a fake mustache in the Mets dugout after being ejected from a game. He also claims to have invented the sandwich wrap.His outsize presence as a first-time candidate who circumvented the party establishment (he will appear on the ballot as a “petitioning candidate”) has generated intrigue in the race far beyond Stamford and made it one of Connecticut’s most expensive municipal races this year. As of the start of October, the candidates had raised close to $1 million and already spent more than four times what was spent on the mayor’s race in 2017. This puts them on pace to break the $1.3 million record set in 2013.This has brought a great deal of attention, especially to Mr. Valentine, who has never held an elective office but is trying to pull together disparate voter blocs in Stamford, where Democrats outnumber Republicans more than 2 to 1 but there are nearly as many unaffiliated voters as registered Democrats.There are doubters, as Mr. Valentine, 71, a longtime Stamford restaurant owner, acknowledged on Oct. 12 in the first mayoral debate, saying that people told him he was trying to do the impossible.“I said, ‘Again?’” Mr. Valentine recounted to an audience of about 150 people at a banquet hall for the debate. “When I was told there was no way of winning in Stamford, Conn., because the voters were dumb and they were lazy, that was my call to action, to make something happen. What I want to make happen is to bring our community together. Not that our potholes are red or they’re blue. Not that our schools are D’s or they’re R’s.”His opponent is Caroline Simmons, a four-term state representative who defeated the mayor, David Martin, in the Democratic primary in September. Ms. Simmons, 35, who graduated from Harvard, previously worked on the Women’s Business Development Council in Stamford and was a special projects director for the Department of Homeland Security before that.Caroline Simmons, center, the Democratic candidate for mayor, canvassing in North Stamford this month.Desiree Rios for The New York TimesYet despite her résumé, Ms. Simmons finds herself battling a celebrity candidate with high name recognition.“It’s definitely a challenge,” Ms. Simmons said on a recent Saturday while knocking on doors and introducing herself to voters in North Stamford. “I have some friends in Boston, and they’re like, ‘What, you’re running against Bobby V?’ ”In the 2020 census, Stamford surpassed New Haven in population having attracted millennials to turnkey apartment buildings along its once-industrial waterfront and tech companies, like the job-search giant Indeed.But with growth has come high housing prices, on top of aging infrastructure and a mold crisis in public schools, all of which has been amplified during the mayoral contest.Ms. Simmons, despite her youth, is clearly the establishment candidate. She doesn’t have Mr. Valentine’s profile or history, but does have the Democratic machine in her corner. Gov. Ned Lamont of Connecticut campaigned in September for Ms. Simmons, whom he endorsed. On Thursday, Ms. Simmons announced that Barack Obama had given her his endorsement.Ms. Simmons also has the upper hand when it comes to ballot placement. Her name will appear on the top line as the Democratic nominee and also the third line, having been cross-endorsed by the Independent Party.Mr. Valentine’s name will appear on Line F, the equivalent to batting sixth on a lineup card, because he is not affiliated with a political party.Famous donors have gravitated toward both candidates. Bette Midler, Michael Douglas and Rita Wilson gave to Ms. Simmons. So did Larry Summers, the former Treasury secretary.Two of Mr. Valentine’s most prominent donors also dismissed him as a baseball manager: Mr. Bush with the Rangers and Larry Lucchino, the former president and chief executive of the Red Sox. The former baseball commissioner Fay Vincent gave to Mr. Valentine, who received the endorsement of police union leaders and the Republican candidate, who dropped out of the race in September.In Stamford, Democrats have controlled the mayor’s office for all but four of the past 26 years. For 14 of those years, the office was held by Dannel P. Malloy, who went on to become a two-term Connecticut governor.But Chris Russo, a former WFAN radio host who has his own channel on SiriusSM satellite radio, Mad Dog Sports Radio, thinks Mr. Valentine has the edge.“I’d be surprised if he didn’t win,” Mr. Russo, who lives in neighboring New Canaan, Conn., said in an interview. “He is Mr. Stamford, and he has been here forever. He’s got a lot to lose. If he goes in there and doesn’t do a good job, it’s going to hurt his legacy.”Mr. Valentine appeared on Mr. Russo’s show on Sept. 11 to reflect on the 20th anniversary of the terrorist attacks, which occurred when he was managing the Mets. Mr. Russo described Mr. Valentine as “glib,” smart and a “young 70,” but acknowledged that people’s perceptions may differ, especially for those not from Stamford.“He can be a little over the top,” Mr. Russo said. “Again, Bobby’s quirky.”Bobby Valentine in 1998 during his tenure as the manager of the New York Mets.Al Bello/Getty ImagesIn one video that emerged online this year, Mr. Valentine appeared to inadvertently record himself while his dog defecated on someone’s lawn and he hurried away. The video has since been removed from YouTube.Ellen Ashkin, 70, a retired public-school teacher who lives in North Stamford and is a registered Democrat, told Ms. Simmons that she would vote for her. As she greeted Ms. Simmons on her doorstep, Ms. Ashkin was snide about Mr. Valentine’s qualifications and his ubiquitous campaign paraphernalia.“Bobby Valentine, really?” Ms. Ashkin said. “Honest to God. The signs are everywhere.”Ms. Ashkin added in an interview that Ms. Simmons faced a unique challenge.“The name recognition of Valentine is kind of scary,” she said.Ms. Simmons is married to Art Linares, a former Republican state senator who proposed to her in a full-page ad in The Stamford Advocate. She is campaigning while pregnant with their third child. She was raised in Greenwich — which the rest of the state regards as somewhat patrician — and moved to Stamford as an adult, which Mr. Valentine’s campaign has sought to exploit. Mr. Valentine frequently tells voters that his family arrived in Stamford in 1910.“I don’t think we consider her a Stamfordite,” Daniel M. McCabe, a lawyer and former longtime Stamford G.O.P. chairman, said before Mr. Valentine and Ms. Simmons debated for the first time.Ms. Simmons said in an interview that she has a proven track record of delivering results for Stamford in the Legislature.“I’ve known my constituents for years, and the issues that they care about,” she said.Early this month, Mr. Valentine regaled about 60 residents of Edgehill, a luxury retirement community, with stories about growing up as a star athlete in Stamford and being the first foreigner to manage a Japan Series winner. He called himself the “protruding nail” that the Japanese “wanted to hammer down.”Mr. Valentine making his case this month at Edgehill, a retirement community in Stamford.Desiree Rios for The New York Times“I was the manager of the year, and I was replaced as manager,” Mr. Valentine said of his career.Before entering the mayor’s race in May, Mr. Valentine spent eight years as the executive director of athletics at Sacred Heart University in Fairfield, which had grown from a commuter school to the second-largest Catholic university in New England after Boston College. He boasted that he had presided over a $25 million budget at the university — a fraction of Stamford’s $615 million city and school budget. He has taken a leave of absence from the job to campaign.Mr. Valentine also emphasized his tenure a decade ago as Stamford’s public safety director in the administration of Mayor Michael Pavia, a Republican. Mr. Valentine likes to tell the story of how, when a major sewer pipe broke in 2011, inundating part of the city with millions of gallons of sewage, he went door to door, telling residents to evacuate to hotels.But Ms. Simmons has seized on Mr. Valentine’s absence from Stamford during Tropical Storm Irene in 2011 — he traveled to Texas for his “Sunday Night Baseball” broadcasting duties on ESPN, a job he kept while being public safety director. A campaign mailer for Ms. Simmons noted, “When Stamford needed Bobby Valentine, he looked out for himself instead.”Dan Miller, Mr. Valentine’s campaign manager, rejected the criticism in an interview, saying that Mr. Valentine was in constant communication with city officials during the storm and had been transparent about his weekend broadcasting commitments when he took the job. Mr. Valentine offered to take no salary, but when that was not allowed donated his entire $10,000 pay to the Boys & Girls Club, Mr. Miller said.Ms. Simmons stood by her criticism.“He abandoned the people of Stamford to go to a baseball game,” she said.Still, this is as heated as it gets between the two candidates. They exchanged few barbs in the first debate, where they vowed to eradicate mold in the schools, fix potholes, cut red tape and recruit new businesses to the city.Ann Mandel, an Edgehill resident who helped to organize Mr. Valentine’s visit there, escorted him through a temperature-screening kiosk and into a community room where dozens of seniors in masks sat spaced apart. Ms. Mandel, a former elected official in Darien, Conn., told him that he could “work the crowd.”“Stamford,” Ms. Mandel told audience, “has never seen a mayoral race like this.” More
