Rollin Woodruff began his career with a significant role in the state militia, later serving as an aide-de-camp to a governor. He held a position in the Connecticut State Senate, where he was chosen as President pro tempore. Woodruff also served as Lieutenant Governor of Connecticut before becoming Governor. Throughout his career, he balanced public service with a successful business career, holding leadership roles in various banks and corporations, as well as serving as president of New Haven's Chamber of Commerce.

Rollin Woodruff's political identity is marked by a distinctive blend of fiscal conservatism and civic engagement, with an unexpected alignment on environmental regulations that suggests a calculated approach to regional economic interests. His tenure as Governor saw him veto several legislative acts as overly expensive, revealing a stringent fiscal stance. Woodruff's deep roots in the state militia and his business acumen, including leadership roles in various banks and corporations, underscore a pragmatic yet principled approach to governance. His membership in historical and civic organizations hints at a commitment to tradition and community, yet his legislative actions reveal a willingness to challenge conventional wisdom.