Matt. Paris, Chron. Maj. iv. 7 and 44 note). On 13 Oct. 1260 he was knighted, with his brother Henry [q. v.], by the king's son Edward. At the opening of the barons' war (1264) he defended Northampton against the king, but was captured after a gallant fight on 5 April, and imprisoned at Windsor.
Released by his father's victory at Lewes, 14 May 1265, he was made 'custos pacis' in Surrey and Sussex (June) and constable of Porchester (24 Dec.) In September-November 1264 he unsuccessfully blockaded an alien garrison in Pevensey Castle; he was at the same task again in June 1265 when called away to help his father in the west. After wasting a month in collecting fresh troops in London, plundering Winchester, and making a triumphal progress to Oxford and Northampton, he reached Kenilworth on 31 July, only to be surprised and routed by Edward next morning. On 3 Aug. he set out again to join his father, but, owing to an unlucky halt at Alcester, he only reached Evesham in time to see from afar his father's head borne off on a spear-point as a trophy of the royalists' victory (4 Aug.) He withdrew again to Kenilworth; there the garrison, in their thirst to avenge the earl, were for slaughtering the king's brother Richard [see Richard, Earl of Cornwall], who was a prisoner in Simon's custody; Simon, however, withstood their demand, and on 6 Sept. set Richard at liberty. On 23 Nov., having fortified and victualled Kenilworth for a long siege, he went to join some of his father's friends who were entrenched in the Isle of Axholme. There, at Christmas, he was forced to accept Edward's terms, and submit himself to the judgment of king and council at Northampton. They pardoned him on condition that he would surrender Kenilworth and quit England for life, with a yearly pension of 400l. He was taken in the king's train to Kenilworth, but when he called upon the garrison to surrender, they refused, clearly with his connivance; he was led back to London, and thence, on the night of 10 Feb. 1266, escaped to Winchelsea. After acting for a time as leader of the Cinque Port pirates, he went over sea. On 18 May a proclamation was issued against his expected attempt to re-enter England by force, and he kept up a correspondence with Kenilworth till the eve of its surrender in December. In September 1267 King Louis of France was negotiating with Henry III for Simon's return to England, but he was still in France on 26 March 1268 (Bémont, Simon de Montfort, p. 251, note 4). Bartholomew Cotton (p. 146, Rolls ed.) says that Simon came over in 1271 to visit the graves of his father and eldest brother; the visit, if it took place, must have been a hasty and stolen one. On 13 March of that year he was at Viterbo, taking part with his brother Guy [q. v.] in the murder of Henry of Cornwall [q. v.], and was only saved from justice by his death in the same year, at a castle near Siena.
[Annales Monastici, vols. ii. iii. iv.; Flores Historiarum ('Matt. Westminster'), vol. iii.; Robert of Gloucester, vol. ii.; Royal Letters, vol. ii. (all in Rolls Series); Chronica Majorum Londoniarum, ed. Stapleton (with Liber de Antiquis Legibus), and Rishanger's Chronicle, ed. Halliwell (Camden Soc.); Rymer's Fœdera, vol. i. pt. i.; Patent Rolls 48 & 49 Hen. III; see also J. R. Green's article on the Ban of Kenilworth in Archæol. Journ. xxi. 277 et seq.]
MONTGOMERIE, Sir ALEXANDER de, of Ardrossan, first Lord Montgomerie (d. 1470?), was the eldest son of Sir John Montgomerie of Eaglesham, Eglinton, and Ardrossan, by his wife Agnes, daughter of Alexander, earl of Ross, lord of the Isles. His grandfather, Sir John Montgomerie (d. 1398?), is separately noticed. The father was a hostage for the Earl of Douglas in 1408, a hostage for James I in 1423, and one of the jury on the trial of Murdac, duke of Albany, in 1425. In 1425 the son was chosen a member of the privy council of James I. He succeeded his father some time before 22 Nov. 1429, and in August 1430 he was, jointly with his brother-in-law, Sir Robert Cunningham of Kilmaurs, appointed governor of Cantyre and Knapdale. On 30 Nov. 1436 he was appointed a commissioner to conclude a treaty with England (Cal. Documents relating to Scotland, iv. 1103), and he was one of the conservators of the truce concluded on 31 March for nine years (ib. p. 1111). With the other Scottish commissioners he received the present of a silver cup from Henry VI (ib. p. 1109). On 5 Feb. 1444 he had a safe-conduct to go to Durham to treat for the extension of the truce and the return of the Scottish hostages (ib. p. 1162).
In 1444 Montgomerie was appointed keeper of Brodick Castle in the Isle of Arran (Exchequer Rolls of Scotland, v. 163). He was one of those who set their seals to instruments passed by the parliament held at Perth on 9 June 1445 against those lords who had rebelled against James II. He was created a lord of parliament by the title of Lord Montgomerie some time before 3 July 1445 (Acta Parl. Scot. ii. 59; Hist. MSS. Comm. 11th Rep. pt. vi. p. 16). On 31 Jan. 1448-9 he had a grant of the office of bailiary of Cunningham. On 14 Aug. 1451 he was a conservator for a truce with England (Cal.
