Dictionary of National Biography, 1885-1900/Sinclair, Oliver
SINCLAIR, OLIVER (fl. 1537–1560), Scottish general at Solway Moss, was the second son of Sir Oliver Sinclair of Roslin [see under Sinclair, William, third Earl of Orkney, and first Earl of Caithness]. Henry Sinclair [q. v.], bishop of Ross, and John Sinclair (d. 1566) [q. v.], bishop of Brechin, were his brothers. He was a member of the household of James V, and is mentioned in the treasurer's accounts in June 1537 as receiving 120l. to pay the king's gentlemen with, and in July as receiving 20l. in ‘complete payment of his livery clothes’ (note by David Laing in Knox's Works, i. 88). On 14 June the king conceded to him and his wife, Catherine Bellenden, the lands of Pitcairnis (i.e. Pitcairn) in the county of Perth (Reg. Mag. Sig. Scot. 1513–1546, No. 1743). According to Lindsay of Pitscottie he was, after the fall of the Douglas family, appointed governor of Tantallon Castle on the coast of Berwick, and on 6 Oct. he received at the king's command a grant for the repair of the castle (note by Laing in Knox's Works, i. 88). He is referred to by Knox as in 1540 ‘a pensioner of the priests,’ and one of the chief in ‘pressing’ and ‘pushing’ the king in his ‘fury’ against the reformers (Works, i. 67). On 3 Sept. 1541 he strongly opposed in the privy council the proposal that James should go to meet his uncle in England, and in August 1542 he came to Jedburgh and seized Sir Robert Bowes, whom he carried a prisoner to Edinburgh (Hamilton State Papers, p. 166).
When at the close of the year the king resolved on a raid into England, he secretly determined that Sinclair should be appointed lieutenant-general. The choice is somewhat unaccountable, for Sinclair, though descended from an illustrious line, was not himself of sufficiently high rank to entitle him to command the higher nobles. It has been attributed to mere favouritism, but it is probable that the king cherished a high opinion of Sinclair's abilities, while he may have thought that his selection was the least likely of any possible one to occasion jealousy. If so, it was not justified by the result, although no other choice might have materially altered it. Letters were sent out to the southern nobles to meet the king on an appointed day at Lochmaben, ‘no man knowing of one another, neither yet did the multitude know anything of the purpose until after midnight’ (Knox, Works, i. 85). Then the ‘trumpet blew and commanded all men to march forward and follow the king, who was supposed to have been in the host,’ but remained at Lochmaben (ib.) The Scots crossed the border into Cumberland, and just before they engaged the enemy (25 Nov. 1542) Sinclair was hoisted on spears ‘upon men's shoulders, and there with sound of trumpet was he proclaimed general-lieutenant and all men commanded to obey him’ (ib. p. 86). But the proclamation seems rather to have caused confusion than inspired confidence. The Scots, now on the banks of the Esk, were apparently unable to agree as to how an attack was to be made, and, as Knox puts it, ‘every man called his own sloghorn’ (slogan) (ib. p. 87). In the rout that soon became general in the direction of Solway Moss, Sinclair, says Knox, ‘was without shot taken fleeing full manfully’ (ib. p. 88).
Sinclair arrived a prisoner at Newcastle on 3 Dec. (Hamilton State Papers, i. xcviii) and reached London on the 19th (ib. p. 335). While a prisoner in London he agreed to an article requiring the king of England to take the young princess of Scotland into his own hands and government (ib. p. 367), and also, with certain others, subscribed a secret article that in case of the young princess's death the king of England should take on him the government (ib. p. 368). He also promised the delivery of Tantallon Castle to Angus (ib.) On these conditions, and that he might aid in furthering the purposes of the king of England, he was allowed to return to Scotland on parole. But on 19 June 1543 Sadler, English ambassador in Scotland, wrote that Sinclair was ‘fourscore miles northward,’ and that he saw not how he could keep his day (ib. p. 545; Sadler State Papers, i. 220). Sinclair was then, it seems, in Orkney, for a summons was about this time issued against him at the instance of the queen mother to deliver up the castle of Orkney (Acta Parl. Scot. ii. 431a, 432b, 442b). Sadler also stated in his letter that he could not find that since Sinclair's return to Scotland ‘he was either well dedicate to the king's majesty, or to the advancement of any of his highness's godly purposes, or yet to the wealth and surety of the governor’ (Sadler State Papers, i. 220). On 22 Nov. Sadler, who had been compelled for safety to take refuge in Tantallon, wrote that he was informed that Sinclair ‘lay at a little house within two miles of Tantallon with three score horsemen’ to catch up him or any of his servants ‘if we stray too far out of the bounds of this castle’ (ib. p. 333). On 12 Jan. 1544–5 he was ordered to enter himself a prisoner into England (Hamilton State Papers, ii. 193), and to this he replied, 16 Feb. 1544–5, that he would, but neglected to say when (ib. p. 553). There is no further account of him, but Knox while writing his ‘History’ refers to him as ‘still remaining enemy to God’ (Works, i. 67).[Reg. Mag. Sig. Scot. 1513–46; Hamilton State Papers; Sadler State Papers; Knox's Works; Froude's Hist. of England, iii. 530.]