Henry Roberts holds a law degree from Yale Law School and attended Yale University and Columbia University. He spent several years in leadership roles within the private sector, notably as President of the Hartford Woven Wire Mattress Company. Roberts transitioned into public service, holding various positions including Alderman, State Representative, State Senator, Lieutenant Governor, and Governor of Connecticut. Post-governorship, he served on the Hartford Water Board and as a Trustee for the Slater Industrial School.

Henry Roberts's political identity is marked by a blend of progressive economic regulations and idiosyncratic public safety measures. His legislative record includes banning basement bakeries and regulating automobiles, revealing an unexpected focus on public health and safety standards. Roberts's approach to family law, with jail sentences for non-support of wives, shows a surprising rigidity in personal responsibility. These positions, coupled with his business background, suggest a highly calculated strategy to balance industrial interests with public welfare.