After completing his education, Roberts practiced law for several years, then entered his father's manufacturing business, the Hartford Woven Wire Mattress Company, and served as company's president from 1886 to 1907. He was also involved in several other business activities.
Roberts became alderman of Hartford, Connecticut in 1897. He became a member of the Connecticut House of Representatives in 1899. He held that position till 1901. He also was a member of the Connecticut Senate from 1901 to 1902. He served as President pro tempore of the Connecticut Senate. He became lieutenant governor of Connecticut in 1903. He held that position till 1905.
Winning the 1904 gubernatorial nomination, Roberts was elected, and became the Governor of Connecticut on January 4, 1905. During his term, several legislations were passed. The bakeries were banned from operating below ground level and a bill was launched that regulated the operation of automobiles. Also enacted during Robert's administration was fortification of the public's safety from fraudulent practices, and the non-support of wives was met with jail sentences.
Roberts left office on January 9, 1907, and returned to his several business activities. He served as president of the Hartford Water Board. He was also a trustee of the Slater Industrial School in North Carolina.[3]
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