I’m Chris Massicotte, and I’m running to be your next Key West City Commissioner for District 5.
I believe Key West deserves honest, responsible leadership that puts residents first.
I was born and raised in central Massachusetts and built a career grounded in accountability and problem-solving. I earned my bachelor’s degree in Accounting with a minor in Computer Science from Villanova University, and began my career as an IT auditor with PricewaterhouseCoopers. I went on to earn a Master’s in Government Administration from the University of Pennsylvania’s Fels School of Government.
That mix of financial discipline and public-sector experience led me to Washington, DC, where I helped modernize political technology. As a founding executive and later Chief Financial Officer of DSPolitical, I brought data accountability and digital innovation to campaigns nationwide.
In 2017, a quick vacation to Key West changed everything. I fell in love with the island’s energy, inclusivity, and creativity and decided to make it home. I co-founded Duval Street Media, a local marketing firm that helps small businesses in the Keys grow through smart digital strategy.
Today, I channel my professional experience into public service:
President of Keys Last Stand, leading efforts to protect water quality, coral reefs, and the character of the Keys.
Board member of Fair Insurance Rates for Monroe (FIRM) and the Key West AIDS Memorial.
Graduate of Leadership Monroe County and the Key West Ambassador Program, where I deepened my understanding of how our local government works — and sometimes, how it doesn’t.
I’ve already proven that I’ll fight for fiscal responsibility. When I urged the City Commission to move a costly special election intended to extend mayoral terms from two years to four from August 2025 to November 2026, the Commission agreed. That single change saved Key West taxpayers $76,000. Imagine what I’ll do when I’m on the dais.
At home in the Casa Marina neighborhood, I live with my husband, Eric, and our rescue dog, Harper. I’m running to make sure Key West remains a community where neighbors look out for one another, not turn their backs when it’s inconvenient — a city where local voices matter more than political pressure, and where our leaders have the courage to do what’s right, even when it’s not easy. Because Key West’s strength has always come from its people — and that’s who I’ll always stand up for.
