GCDS News - Magazine

For Caroline Simmons ’01, election night came down to the wire. “My family and I were at my house all huddled around a computer in the kitchen, waiting for the results to come back. It was neck-and-neck the whole time,” recalled the GCDS alumna. “We were waiting to hear from 20 polling stations—in one poll, we would win by a couple of hundred votes and in another we would lose by that much.” 

It wasn’t until midnight as Ms. Simmons and her family were making their way to campaign headquarters that she found out that she had won the election to be the new Mayor of Stamford, CT—the first woman elected to that position in the city’s history.

In the end, 1,500 absentee ballots put her over the top. 

On Jan. 24, two months into her term, Mayor Simmons joined Head of School Adam Rohdie and Taylor Glasebrook ’97, Chair of the Alumni Advisory Council (AAC), from her office in City Hall for a Masterclass Zoom conversation. Alumni, students, faculty, and parents, past and present, logged on to the program sponsored by the AAC, to learn about her priorities as mayor, her life in public service, and her memories of Old Church Road. 

Ms. Simmons is humbled by the historic nature of her election. 

“To all of the women and girls in our city, today is for you,” she said at her swearing-in ceremony at the Stamford Government Center. “I know today as I take this oath that I’m just picking up a torch that many of you have been carrying for a long time and that the young girls watching today will be picking up long after me.”

During the campaign, Ms. Simmons encountered skepticism about whether a 35-year-old mother could run the city. She noted that only 20 percent of U.S. mayors are female. Since she has been on the job, however, she has been pleasantly surprised. “In office, I haven’t really experienced many gender-related issues. I just concentrate on the work with my great team. But I’m not naive to think that it may not resurface at different times.”

In her two months as mayor, she has been doing what she promised—staying focused on improving people’s lives in Stamford. 

“We have the ability to touch constituents’ lives directly on issues, whether it’s their roads, schools, or the quality of their neighborhoods. As mayor, I take that task really seriously and ask myself daily: What did I do to help people today?”

When Ms. Simmons is not addressing the city’s immediate needs, such as COVID and weather-related issues, she and her eight-member cabinet are tackling their five 100-day strategic priorities: 1) improving the city’s infrastructure 2) better investing in city schools 3) enhancing economic prosperity for residents 4) making the city more affordable and equitable 5) improving constituent services and responsiveness. 
Ms. Simmons’ road to City Hall was preceded by a career in federal and state government—first at the Department of Homeland Security and then as the State Representative for the 144th House District. 

“I felt that there was this shift in policy making taking place from the federal government to state and local governments,” she said pointing to the gridlock in Washington. 

Like many others in her generation, she was drawn to public service because of 9/11. “In the aftermath of that tragedy, I was very inspired by the ability to do good, watching the firefighters, first responders, and volunteers at Ground Zero. That led me to study and pursue international affairs and counter-terrorism work, ending up at the Department of Homeland Security.”

Ms. Simmons remembers feeling frustrated by the lack of urgency regarding gun violence in Washington, a cause about which she cares deeply, especially after the shooting in Newtown, CT. She saw that state governments were making progress  around this issue. This prompted her to run for state representative.

Ms. Simmons’s passion for public service and politics started early around the dinner table with her parents and four siblings, Sara Simmons Bartow ’98, Julia Simmons ’03, Nick Simmons ’04, Cliff Simmons ’07, all GCDS alumni. 

“I’ve always loved politics. I grew up in a political family. My dad was a Republican and my mom’s a Democrat. My siblings and I would hear them debating politics at the dinner table and they would take us to national political conventions. This sparked an early interest.” 

She credits Country Day for teaching her how to be a good public speaker and writer, skills that she uses every day in her role as mayor.

“Country Day provides this incredible foundational education for communication skills, both speaking and writing. I’ve used them throughout my career and they’re so important no matter what you decide to go into,” she said, recalling Ms. Harris’ grammar lessons and Mr. Kelly’s help with speeches. 

Despite a divided two party political system, Ms. Simmons, a Democrat, believes that bi-partisanship is essential. 

“The best policy making comes out of collaboration. I’ve always believed in reaching across the aisle. Instead of attacking each other, let’s attack the problem,” she said. “Things may still get heated, and we don’t always get to a perfect solution, but I think if we can remember to put people first and try to put politics aside, we’ll all be better off.”

Not only does Ms. Simmons reach across party lines, but she also reaches out to her colleagues in Hartford. In fact, she is in regular touch with GCDS alumnus 
station, roads, and bridges and we need to be shovel-ready and prepared,” said Ms. Simmons. 
“So much of what we encounter on a day-to-day basis, whether it’s navigating the COVID pandemic or education issues, requires collaboration with state and federal partners to advance our city.”

During the Q&A portion of the interview, a student participating on the webinar asked for advice about working in government. Ms. Simmons said that it’s never too early to get involved and educated. 

“Get yourself acquainted with the issues and see what you are passionate about. Don’t give up the first time you try and run for office, putting your name on a ballot is an incredibly rewarding experience. And remember, there are a lot of ways of getting involved behind the scenes, at the non-profit level, working on policy.”

She remembered running for Class Rep in ninth grade and losing. “It wasn’t even close,” she recalled with a laugh. 

Ms. Simmons praised GCDS for its cross-disciplinary, collaborative approach to education, particularly in the new high school. “It lays the groundwork for a set of skills that is going to be very beneficial to the students in the future, in college and in their careers. It’s definitely the way we try to work in City Hall.”