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 according to William Maitland of Lethington—who recommended him to Lady Cecil, on his way through London, as a ‘near relative of his own’—for the recovery of certain debts due to him from the late queen-regent (Cal. Hatfield MSS. i. 250). Not improbably he was employed by Maitland on some private political mission; and he seems to have remained in France until after the death of Queen Mary's husband, Francis II. That he won the special confidence of Queen Mary may be inferred from the fact that he was chosen one of her commissioners on 12 Jan. 1561 to intimate the death of the king to the privy council of Scotland (, Lettres de Maria Stuart, i. 85; Cal. State Papers, For. Ser. 1560–1, entry 880).

When Queen Mary arrived in Scotland, Preston became one of her most trusted friends, and she made him captain of the important stronghold of Dunbar (ib. 1564–5, entry 181). On the outbreak of the rebellion of the Earl of Moray and others after the queen's marriage to Darnley, the queen on 23 Aug. 1565 sent a letter to the bailies and town council of Edinburgh ordering them to displace Archibald Douglas of Kilspindie and to ‘elect, admit, and own our lovit Symon Preston as provost’ (Letter in Extracts from the Records of the Burgh of Edinburgh, 1557–1571, p. 199, and in Hist. of Edinburgh, p. 26). When, on 31 Aug., the forces of the rebels, under Moray, advanced towards Edinburgh, Preston caused the common bell to be rung to summon the inhabitants to resist his entrance; and, although he did not succeed in preventing this, the attitude of the inhabitants was so hostile, that Moray, failing to obtain any support either in soldiers or money, was compelled to depart as soon as news reached him of the approach of the queen's forces. In order to raise money for payment of the Queen's troops, Preston, after several of the principal inhabitants had declined to raise the loan, effected an agreement by which the city undertook to pay immediately ten thousand merks sterling, and to have the superiority of Leith in pledge, upon condition of redemption (Extracts from the Records of the Burgh of Edinburgh, 1557–71, pp. 207–8). By this bargain Edinburgh retained the superiority of Leith for nearly three hundred years. Randolph refers to Preston as ‘a rank papist’(Cal. State Papers, For. Ser. 1564–5, entry 181); but Knox, although denouncing Preston as ‘a right epicurean’ for his adherence to the queen after the murder of Riccio (Works, i. 236), admits that after the crisis following the marriage to Darnley he ‘showed himself most willing to set forward religion, to punish vice, and to maintain the commonwealth’ (ib. ii. 511). On 5 Nov. 1565 he was elected a member of the privy council (Reg. P. C. Scotl. i. 389), and in the same month he was also appointed one of a commission to take order for the proper mounting of the artillery of the realm (ib. pp. 402–403). After the murder of Riccio on 9 March 1565–6, Preston, as provost of the city, caused the common bell to be rung, and passed to Holyrood Palace with four or five hundred armed men; but, on being commanded by Darnley to return home with his company, immediately retired (, ii. 522). On 2 Aug. 1566 the bailies and council, in recompense of his services to the burgh during the past year, conferred on him the gift of the goods of Thomas Hoppringill, which had been escheated (Extracts from the Records of the Burgh of Edinburgh, 1557–71, p. 216). Subsequently Preston was in close alliance with Bothwell and the queen. Mary was staying at Craigmillar Castle when the scheme was mooted for ridding her of Darnley; and she also at first proposed, or professed to propose, to bring Darnley to Craigmillar for change of air, when he accompanied her from Glasgow. After the queen's marriage to Bothwell, however, Preston supported the lords; and in the name of the magistrates of Edinburgh, he, on 10 June 1567, signed the band for the deliverance of the queen from Bothwell and revenge of the murder (ib. p. 233; Reg. P. C. Scotl. i. 527). When the queen was convoyed by the lords into Edinburgh after the surrender at Carberry Hill, she was lodged, until the evening of the following day, ‘in the Provests loging [or town house], fornent the croce, upon the north syd of the gait’ (letter of Archbishop Beaton in Hist. ii. 113). On 8 May 1568 Preston entered into a bond with Sir William Kirkcaldy [q. v.] of Grange to maintain the cause of the king and regent (, ii. 412–3; Cal. State Papers, For. Ser. 1572–4, entry 944). In 1569 he was succeeded in the provostship by Kirkcaldy. On 2 June of the same year the king conceded to David Preston, son and heir-apparent of Simon Preston, the lands and barony of Craigmillar, with the fortalice, &c., which Simon resigned (Reg. Mag. Sig. Scot. 1543–80, entry 1860). In June 1570 he was in Paris, whence, on the 12th, he wrote a letter to Cecil, informing him of a proposal made to the French king on behalf of the Queen of Scots (Cal. State Papers, Scott. Ser. i. 291). He died some time before 8 March 1574–5 (Reg. P. C. Scotl. ii. 436).

By his first wife, Elizabeth, daughter of