Chris Drago grew up in Dutchess County, NY, and graduated from Millbrook in 1992. Following high school, he served as an Assistant Teacher with AmeriCorps before attending Vassar College.

Over the course of his 20+ year career, Chris rose to become a business executive in digital marketing, leading teams at top-tier agencies such as Interpublic, OMD, and Ogilvy, and also at global brands like HP/Hewlett Packard Enterprise, Mailchimp, and Airtable. In these roles, he oversaw budgets exceeding $100 million and negotiated partnerships with Fortune 500 companies.

In 2023, after a year-long campaign, Chris was elected as a Dutchess County Legislator, representing a 170-square-mile district that includes Stanford, North East, Pine Plains, Eastern Red Hook, and the Village of Millerton. As a Legislator, he serves on the Public Safety and Family & Human Services subcommittees and is an advocate for a more affordable Dutchess County. His priorities include improving access to emergency services, mental health resources, transportation, and affordable housing in Northern Dutchess.

Chris also serves on the Board of Directors of the Sharon Playhouse in Sharon, CT, where he contributes to fostering the arts and community engagement. He lives in the Town of Stanford with his partner, Eric, and their two Labrador Retrievers, Tia and Sasha—just a few miles from where it all began at Millbrook.