Home Fairfield Bobby vs. Caroline: 2021 Stamford Mayoral Race

Bobby vs. Caroline: 2021 Stamford Mayoral Race

The 2021 Stamford mayoral race is shaping up to be one of the most exciting in recent history, thanks in no small part to a celebrity candidate with high-name recognition, Bobby Valentine.

The former Major League Baseball player and manager is facing off against 35-year-old Harvard graduate and four-term state representative, Caroline Simmons.

While the 71-year-old Valentine might have the name recognition, Simmons firmly has the Democratic machine behind her.  Connecticut Gov. Ned Lamont campaigned for Simmons in September, and just last week Barack Obama – for whom she served in the Department of Homeland Security — endorsed her candidacy for mayor. Simmons was also endorsed by the Independent Party. Democrats have controlled the mayor’s office for all but 4 of the past 26 years.

Valentine is running unaffiliated and will appear on the ballot as a “petitioning candidate”; he has never held an elective office before.

As of the 2020 census, Stamford has surpassed New Haven to become the second-largest city in the state behind Hartford — and as a result its mayoral election has garnered attention far beyond the city limits. Both candidates have received donations from bold-faced names in entertainment, sports and business.

I sat with Caroline and Bobby to learn more about the individuals behind the personas and what policy agendas matter most to them.



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