Osborne rose to prominence during the Northumberland régime, then fell out of favour under Mary, when his sympathies were with his relative Sir John Cheke and the protestant reforming group. He may have been imprisoned. He is not known to have been a Marian exile. At Elizabeth’s accession he was reinstated at the Exchequer, where he was employed in 1560 in connexion with the new coinage. A number of letters to his master and marriage relation Sir William Cecil survive, mainly on the subjects of general foreign trade, customs duties and commercial treaties. On 9 Oct. 1572 Osborne sent him a resumé of the personnel of the Exchequer and their responsibilities, and in the same year he was making a collection of statutes, letters patent and charters relating to English trade since the reign of Henry III. The friendship between the two men outlasted Osborne’s death, for Burghley looked after Osborne’s son John, for whom he had already secured the reversion of the remembwrancer’s office, ‘the stay of his house, his wife and children after him’, until 1698 in fact. Though Osborne bought a small amount of landed property, unusually for the period he refrained from speculating with public money, and his estates were not extensive. He bought South Fambridge in 1561 and Chicksands priory, Bedfordshire in 1576. The family remained at Chicksands, and were in the royal service at least until 1812, and MPs until 1824.
Osborne owed all his parliamentary seats to Cecil. A letter is extant
By 1587 Osborne was suffering from the stone, and in the spring of 1591 he was ‘at more leisure from Westminster and going abroad, by reason of my lameness and sickliness, than heretofore’. He died 7 June 1592, and was buried at St. Faith’s under St. Paul’s. No will has been found.
