Richard was married to Lydia Trowbridge (born 1666), daughter of Thomas and Sarah (Rutherford) Trowbridge II. Governor Benjamin Fletcher of New York stated in 1693 that: “Major Palmer, Mr. Bulkely, the two Rosewells (Richard and William) and Mr. Trowbridge are gentlemen of the best education sense and estates among them” (referring to people of Connecticut).
Richard and Lydia were married in 1681, when Richard was 29 and Lydia was “less than 16 years of age.” He was described in an early history of Yale University as “a newly settled West India merchant in James Pierpont’s distant New Haven congregation.” In 1701 he was appointed treasurer of the newly founded “Colony Collegiate School” in Saybrook–now better known as Yale College. (There is an earlier treasurer listed on the roster for the founding year of 1701, Nathaniel Lynde, but there is speculation he either turned down the office or immediately resigned.) After his death in 1702, he was succeeded by John Alling of the Alling family.