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Now, after a lifelong career in sports, Major League Baseball legend Bobby Valentine wants to be Stamford's mayor for real.
In a week, on Tuesday, Nov. 2, voters will make the call in a race that has drawn national attention and even seen each candidate endorsed by a past United States president.
"Tommy Lasorda would introduce me either as the mayor of Stamford or ambassador of Stamford," Valentine says, referring to the late Los Angeles Dodgers manager.
The 71-year-old Valentine can't pinpoint the exact date he decided to run for the actual office but said it happened sometime early this year.
"It came over dinner when there was a conversation that the current mayor (David Martin) served two terms as a Democrat, served 35 years on boards in the city, and that he was being primaried by his own party," Valentine said. "The candidate (State Rep. Caroline Simmons, a Stamford resident) kind of got dropped in our area to win a seat."
Valentine said the discussion about a potential run was with two Stamford residents.
"I was with a guy I grew up in Stamford with and a friend of his who lives in the same apartment building in downtown Stamford," Valentine said.
Valentine said it took that encouragement to push him to run.
He officially announced his candidacy on Friday, May 7, saying he was running not as a Republican, Democrat, or even as an Independent.
"Running as 'Unaffiliated' - not to be confused as an Independent - is something people are excited about," he said.
Valentine said his family first arrived in Stamford in 1910, and he cited his years as a businessman in the city (the owner of Bobby V's Restaurant and Bar).
He also served in then-Stamford Mayor Michael Pavia's Cabinet as Stamford Public Safety Chief for part of 2011 before leaving the position when he was named Boston Red Sox manager at the end of that year.
"My main takeaway of the last five-plus months of campaigning is that for the most part people are really tired of the partisan divide that the two-party system has created here in the city and in the nation," Valentine said.
"The candidate that is running has divided the Democratic party in Stamford," Valentine said. "The party itself is divisive in most everything they do. People are tired of that political divide, especially in a city as diverse as we are and as successful a city. They want a unified effort moving forward."
Simmons has been endorsed by former President Barack Obama, and posted a photo with him on Twitter, saying "President Obama understands what is at stake for our community on November 2 and I'm incredibly honored to receive his endorsement."
"I never saw the photo," Valentine said. "I'm not sure what to take out of it."
Valentine, meanwhile, has been endorsed by former President George W. Bush, who was managing partner of the Texas Rangers when Valentine served as their manager from 1985 to 1992. In addition to the Red Sox, he also managed the Mets from 1996 to 2002.
He's also been endorsed by former White House communications director Anthony Scaramucci, and Greenwich resident Linda McMahon, who served as administrator of the Small Business Administration in the Trump administration.
Beyond those big names, Valentine says he's "swayed thousands of Democrats" in Stamford to support him.
"I remember growing up my mom would tell my dad who she voted for and he would tell her who he voted for," he said. "I think they were from opposite parties. The idea of hate was not part of the vernacular of being a politician. If you did something during the campaign that seemed to be negative, it worked against you."
Despite being on both sides of thousands of wins and losses during his time as a player, manager, and as athletic director at Sacred Heart University in Fairfield, Valentine has no prediction on what the result will be on Nov. 2.
"I have no idea," he said. "This is my first time testing these waters.
"But I can tell you about the eyes and ears test when I'm walking the streets. I get a really good feeling."
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