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My passionate hobby is studying art history, particularly American antebellum portraiture. I am absolutely certain that your portrait image of William E. Woodruff (1795-1885) was painted by Kentucky painter Alexander Bradford (1791-1827). That would also change the apparent date from "ca. 1830" to something like "ca. 1826." He was engaged much of 1825-26 painting the eight members of the Prewitt family, several of whose portraits bear a very close resemblance to this portrait (for example, Levi Prewitt).
Your article on Woodruff mentions the printer Thomas Bradford. The Bradford family in this part of America was headed by John Bradford (1747-1830), who set up the first newspaper west of the Alleghenies and whose several sons followed in the business. This family also had two portrait painters (John V. & Alexander Bradford) who worked in the 1820s.

Jon Bernard
Kilauea, HI