Passing over the quarrel between King James II. of Scotland and the eighth Earl of Douglas, in which the latter was stabbed by teh King; and the battle of Arkenholme in 1454, when James, ninth Earl of Douglas, was defeated chiefly through the defection of Lord Hamilton, we come to the forfeiture of the Douglas family, which was resolved upon by parliament in the year 1455.  Four years subsequent to that event, viz, in 1458, Sir Walter Scott of Kirkurde, received a grant, under the Great Seal, of the lands of Abbingtoun and Glengouar, in Crawfordjohn, for his good service at Arkinholme, and in 1464 these lands, forming half of the barony of Crawfordjohn,were bestowed upon James, Lord Hamilton, for his services on that occasion.  (Reg. Mag. Sig., vii. 253.)    James, second Lord Hamilton and Earl of Arran, obtained in 1512 a confirmation of this grant to his father, with remainder to his legitimate heirs-male, whom failing ot Sir James Hamilton of Fynnart, his illegitimate son.  (Ibid., xviii.)   It is probable that James, first Lord Hamilton, had obtained possession of Draffan, as he did the half of Crawfordjohn, on the forfeiture of the Douglases, although it is remarkable that such fact should not clearly appear in any public document.

The date of his appointment has heritable bailie to the monks over the barony of Lesmahagow, in 1456-7, as given by Hamilton of Wishaw, corresponds with the date of the Douglas forfeiture, but there is nothing in the chartulary of Kelso to warrant the statment made by Wishaw, that he held these lands of Draffan from the monks.  Lord Hamilton had a gran of the lands of Fynnart, in Renfrewshire, forfeited by the Earl of Douglas, from James II., in 1457 and of part of Bothwell in 1471 and 1473.   (Anderson's "History of Hamilton," p.61; and "R.M.S., " vi. 3 and vii. 133.)

The career of Sir James Hamilton of Finnart, his natural son, is remarkable, but being so fully detailed in history, the notices of him in this work must be brief.

In 1532 he was appointed baron-bailie of Lesmahagow, and in 1538 he received a grant of the Castre de Nauthane (Nethan Castle) and the lands thereof, also of Crossford.  (Reg. Mag. Sig., xiv. 483 and xxvi 210)  The castle, of which some idea may be formed from the interesting ruins which remain, was probably a reconstrucion, and it is possible that the site may have been that of a still earlier residence, and of the chapel granted to Lambyn Asa on the lands of Draffan, where there was service three days a week.   That Sir James Hamilton had a chapel is manifest from a curious entry in the treasurer's accounts, immediately after his forfeiture in 1540, which is subsequently given in this book.

Sir Jame's mother was daughter of Lord Boyd, or as some affirm, of Boyd of Bonshaw, in Renfrewshire.  A charter to Finnart, by his father, was confirmed under the Great Seal in 1507, and his legitimation passed the Great Seal in1512.  In 1520 we find him at the head of 400 Merse men, against the Earl of Angus, in a quarrel between that nobleman, then governor of the kingdom of Scotland, and Ker of Phairniehurst, regarding jurisdiction connected with the Jedburgh forest, which was claimed by the latter as seneschal or bailie of the monastery of Dryburgh.  The men of the Merse deserted Hamilton in the beginning of the conflict, and five of his horsemen being killed and thirty taken prisoners, he was forced to fly for safety to Home Castle, which he reached with difficulty, being closely pursued by John Somerville of Cambusnethan, to whom some accounts attribute the whole frame both of the attack and pursuit.  ("History of the Somervillis.")

In April of the same year, when Parliament had assembled to deliberated upon the dangerous power which the Douglases had acquired, Sir James became involved in a street brawl, between the Angus and Arran parties; the object being to apprehend and control Angus, whom the Hamiltons dreaded.  Sir Patrick Hamilton, Arrans brother, having rushed out with the Arran party upon the Earl of Angus, fell during the scuffle.   The Earl of Arran and Sir James fought their way through the combatants, and retreated down a wynd on the north side of the High Street of Edinburg, where, finding a coal horse standing, they threw off his burden and rode through the North Loch at a narrow place, no one thinking of pursuing them that way.  (Anderson's House of Hamilton.")  Tytler remarks upon this unfortunate affair, that Hamilton of Finnart was a man distinguished for his ferocity, and by upbraiding Sir Patrick Hamilton for cowardice, he prevented Gavin Douglas, the celebrated Bishop of Dunkeld, from being successful as a peacemaker between the contending parties.

The name of Sir James Hamilton occurs in a respite, dated 1st July 1523, to several noblemen, "for treasonable arraying of battle, insurrection, and fielding, against John, Duke of Albany, and for other treasons, slaughters, etc., during the space of nineteen years."

In September of same year, a battle took place at Linlithgow, between the united followers of the Earls of Angus and Arran and the adherents of the Earl of Lennox, who was so great a favourite with the King, that it was proposed to make him Regent and heir to the crown, in prejudice of the rights of the Hamilton family.  During the heat of the action, Lennox was wounded and taken prisoner, and was being conveyed to a place of safety, when Sir James Hamilton, to his lasting disgrace, slaughtered him in cold blood.

In the following year the good understanding between the Douglas and Hamilton families was nearly interrupted by the following incident, which occurred at Holyrood.  During a review of the Hamiltons and Douglases in the court-yard, a groom of the deceased Earl of Lennox, to revenge his master's death, resolved to assassinate Sir James Hamilton, and attacking him on the stairs of the Palace, inflicted upon him six wounds.  Great confusion ensued, and the Hamiltons, thinking that the deed had been done at the instigation of the Douglas party, were preparing to avenge it when the assassin was recognised and apprehended.  Sir James, as some atonement for the cruel deed which had occasioned this difficulty, and in accordance with the customs of the times, granted ten merks yearly from his lands of Strathaven, to the preaching friars of Glasgow, to say masses for the soul of the murdered Lennox.  His interest at Court continued, and in the following year he was appointed captain of Dumbarton Castle.

In 1535 it was the leading feature of Henry VIII. of England's policy ot induce his nephew, the Scottish King, to throw off the yoke of Rome, and establish the Reformation in Scotland; and to this end he made an earnest proposal for a marriage between his daughter, the Princess Mary, and James V.  The latter acting by the advice of his Privy Council, who were mostly composed of ecclesiastics, and described as "the Pope's pestilent creatures,"  refused both proposals; and an embassy was despatched to France for the purpose of concluding a matrimonial alliance with that Crown, but so effectually was English interest exerted, both at the courts of France and Scotland, in creating obstacles to the alliance, that in 1536 the King secretly resolved to leave his dominions in disguise and sue in person the hand of Marie of Bourbon.  H was accompanied by Sir James Hamilton, but the vesses having encountered a gale, the King, who had fallen asleep, found on awaking that he was landed on the coast of Scotland.    Some of our historians have ascribed this result, not to the gale, but to the jealousy of Hamilton, who, in common with the rest of that family, were opposed to the match, as being likely to defeat their expectations of succeeding to the throne.    Tytler remarks that it may be questioned wheter they would thus publicly expose their ambition.