Iain Stuart MacDonald was born on the island of Skye off the Western coast of Scotland in 1330. He was the illegitimate son of John MacDonald of Islay, the Lord of the Isles[1]. Named Iain (John) after his father, and Stewart (or Stuart), in honor of Walter the Stewart, a great friend of his father, he was reared by his mother’s family until the age of 12, when his mother died. He was then taken to his father’s court. At his father’s insistence he adopts the last name MacDonald, and begins using “Stewart”, or “Stuart” (spellings vary) as a first name to avoid confusion with his father.

Stuart thereafter lived at his father’s court on the island of Islay. Due to his father’s extensive connections with the continent and in England, he was given the traditional European education in arms, but because of his illegitimate status was never fostered upon a noble family. As part of his military education, he frequently traveled with his father on the raids and punitive expeditions that John of the Isles used to cement his control of the Hebridies. Being an acknowledged bastard, he seems to at times have been used as a confidential courier for his father, for matters when his father did not wish to make a public political statement by appearing in person.

In 1347 Stuart was appointed an Esquire to Edward Baliol[2], the English backed pretender to the throne of Scotland. This is seen by many to be an extension of his father’s political machinations. At this time “Good John” of Islay, was in correspondence with both claimants to the throne of Scotland, as well as King Edward III of England[3]. Stuart served Baliol on his campaign into the Galloway[4] district of Scotland following the defeat of a Bruce faction led Army at the battle of Neville’s Cross[5]. Stuart’s service was evidently well received, as he was knighted by Baliol in 1348. Stuart continued in Balliol’s retinue for a further two years, gaining valuable experience in the clashes between the Baliol and Bruce factions along the Scottish border.

In 1350, probably with the political connivance of his father and King Edward III of England, Stuart was hired into the retinue of Sir Thomas Beauchamp, 3^rd Earl of Warwick[6]. This allowed Stuart, and by extension his father, to disassociate from the unpopular and unsuccessful Edward Baliol. Stuart was paid 2 Shillings a day[7] as well as an £18 Regard[8] payment (a sort of signing bonus) by Warwick. Sir Stuart’s war horse, listed in the Restoro Equoram[9] rolls as a Courser, was valued at £19, 6 shillings, 8 pence, about average for a horse in Warwick’s retinue.[10] Stuart served in Warwick’s retinue for the next 5 years, making frequent trips to France to participate in the Chevaunchees of King Edward and his son Prince Edward of Woodstock. (later known as “The Black Prince”) Thus began Sir Stuart’s service in the series of conflicts that would eventually come to be called the Hundred Years War.

In the Summer of 1355 Sir Stuart accepted another indenture from the Earl of Warwick, this time to provide 5 Men at Arms and 10 Mounted Archers for the Earl’s retinue. This is a significant step up for an un-landed knight, indicating that Sir Stuart had done well in the wars, attaining at least enough wealth to support the upfront cost of arming and equipping 15 men for the upcoming campaign in southern France. This promotion would make Stuart a Captain in his own right, rather than just a landless knight serving in another knight’s retinue. It would also entitle Sir Stuart to collect a share of ransoms and plunder from the men who served under him. The traditional split appears to have depended upon whether the captain supplied the man with a horse or not. Those who supplied their own horse, owed the Captain 1/3 of their loot, while those who rode horses belonging to the captain owed him ½. By the same rule, Sir Stuart would in turn relinquish 1/3 of all his winnings to the Earl of Warwick, who will give 1/3 of his ransoms and booty to his commander.[11]

Starting in October of 1355, Stuart, riding in the Van with the Earl of Warwick, participates in Prince Edward of Woodstock’s great chevaunchee of 1355 into the Languedoc region of southern France.[12] This raid was unopposed by the French and pillaged its way to the Mediterranean coast at Narbonne on November 8^th. Here the Prince reversed his course and marched along a different route back to his capital at Bordeaux, having ridden a total of 675 miles.[13] He had deprived the French of inestimable wealth, and shown that once again the French were unwilling to meet him in open battle. Stuart’s share of the plunder from this raid (estimated to have been around £420) far exceeds his pay, and bring him his first taste of real wealth.

Sir Stuart, along with the rest of The Earl of Warwick’s retinue, remained under arms throughout the winter of 1355-1356, quartered in the Bastide of La Reole[14]. Frequent small raids kept them busy harassing the French border throughout the winter. Stuart’s familiarity with this region would later influence his decision to purchase estates here.

The following year finds Stuart still in the employ of The Earl of Warwick, now leading 12 Men at Arms, and a full “Vintaine” of 20 Archers[15], all of whom are mounted. On September 17, 1356, at a farm called La Chavoterie, an English scouting party is overtaken by a French force led by Raoul de Coucy, Sieur de Montmirail.[16] They engage and, though outnumbered the English route the French and take several captives. [17]Sir Stuart captures Raoul, a very wealthy knight who is the uncle of the Lord Enguerrand VII de Coucy,[18] one of the richest nobles in France.

The next day, September 18, 1356, Sir Stuart fought in the Vanguard of the English army at the battle of Poitier.[19] During the heavy fighting on the English Left, he captured 3 French Knights, to hold for ransom. He later sold these prisoners to The Earl of Warwick for the sum of £800. He also took booty from the French camp worth about £200. Taken together with the enormous ransom of Raoul de Coucy, (which was rumored to be in excess of £1,200) and his share of his men’s plunder, Stuart became a moderately wealthy man. In 1357, Sir Stuart used part of his new found wealth to purchase a small castle with estates in the Gascony, from Jean de Grailly, the Captal de Buch[20], a Gascon Count. For the first time Sir Stuart became a landed knight. In addition to the obvious advantage of having a steady income from his estates between campaigns, the social advantage of being landed nobility cannot be overstated. Ownership of lands elevated him to the ranks of the minor nobility. For the next few years he seems to have applied himself to the management of his estates which were wine producing lands in the Gers region on the borders of Gascony.

From 1362 to early 1365, Stuart Crusades to Lithuania with Thomas Beauchamp[21] where he joins the Teutonic Knights in their campaigns against the Pagan Lithuanians. Stuart lodges at Malbork (Marienburg) Castle[22] when not in the field. On the Earl’s return to England in 1365, Stuart is granted estates in Warwickshire for his loyal service. (Partly in lieu of back pay) The lands being vacant since the Pestilence, Stuart hires a Bailiff to run the estates, peasants who work directly for wages and housing, and raises sheep for wool and meat. He will later transfer some of his horse breeding stock to these estates due to the instability of French/English relations in Gascony. These estates bring in about £90 per annum.

In 1362, Stuart’s father arranges the marriage of Sir Stuart to Lady Edain Ingen Raghailligh, an Irish girl who was the daughter of the Lord of Breifne, a powerful noble from central Ireland. Since Stuart was away on crusade, the wedding was held by proxy at his father’s court on Islay. Edain, with her small entourage, moved into Stuart’s Gascon estates while he was away.

In September 1365, shortly after returning from Lithuania, Sir Stuart takes service with the French knight Sir Bertrand Du Guesclin for a campaign into Spain in support of Henry of Trastamera, one of the two contenders for the throne of Castile. In 1366 during Pedro the Cruel’s retreat from Toledo[23], Stuart captures a Spanish knight. Stuart keeps the Knight’s Destrier, and invests the ransom money in buying Spanish mares for breeding stock. He returns to his estates in Gascony, where he begins raising and training warhorses from his Spanish stock. Due to the end of Restoro Equoram[24] payments for English troops serving in the Aquitaine, demand for trained warhorses in the region is at an all time high. (Horses shipped from England to Gascony had to be rested for at least a week before being used on campaign, to avoid a fatal condition known as “the strangles”[25]. Combined with losses at sea from piracy, sickness and shipwreck, many English men-at-arms chose to take their increased Regard payments and use them to buy horses once they were safely landed in Gascony) The business venture thrived, adding considerably to Stuart’s income.

In 1367 Stuart accepts an indenture from Sir William Beauchamp (son of Thomas Beauchamp) as a favor to his old friend and commander, for the campaign into Spain under Prince Edward of Woodstock. Ironically, Stuart will fight on the opposite side in the same war he fought with Du Guesclin in 1365 and 1366. On April 3 of 1367 Stuart fights in the vanguard at the Battle of Najera[26], commanded by John of Gaunt, Duke of Lancaster. He captures a Spanish Knight and paroles him to gather his ransom, which Stuart never collects. While he collects his daily pay and a double regard payment, it does not make up for the loss in horses that he and his retinue suffered crossing the Pyrenees Mountains in winter.

In 1369, Stuart once again indentures with Thomas Beauchamp, the Earl of Warwick, for an expedition to France, again for 12 men at arms and 20 mounted Archers. On November 13, 1369, Thomas Beauchamp, 3^rd Earl of Warwick, dies of the Pestilence while at Calais[27]. Stuart escorts his friend’s body back to England and is present at his funeral and burial at St. Mary’s Church in the town of Warwick. Sir Stuart is pictured as one of the “Weepers” on Earl Thomas’s tomb. After doing homage for his lands in Warwickshire to Thomas Beauchamp, 4th Earl of Warwick, Sir Stuart returns immediately to his Gascon estates due to renewed fighting with the French.

In 1370, French forces renew their campaign to retake formerly French portions of the Aquitaine. Stuart evacuates his wife and the non-military members of his household to Bordeaux and later to his estates in Warwickshire. He also removes the majority of his Spanish horse breeding operation to England and prepares his castle for siege. Sir Stuart plays an active role in the fighting, under his Lord, the Captal de Buch, from whom he holds his Gascon estates. He is present at the death of Sir John Chandos, an old friend and comrade, on the bridge at Lussac in January[28]. In July of 1372 Stuart’s castle comes under siege by French forces. Ironically these forces are commanded by Sir Bertrand du Guesclin, now the Marshal of France.[29] After a siege of 7 weeks, Stuart is forced to surrender due to overwhelming French numbers and dwindling supplies. His castle is “slighted”, and Stuart is released to gather his ransom, set at £480. In 1373, after paying his ransom, Stuart returns to France, this time at Calais, where he participates in a chevaunchee led by John of Gaunt, the Duke of Lancaster into the heart of France. It captures no towns or castles, and accomplishes nothing but killing thousands of English soldiers and horses by starvation[30]. Stuart retires in disgust to his Warwickshire estates vowing to “fight in France no more.”

Stuart seems to have kept his vow, and never returned to France. He continued to serve The Earl of Warwick, and spends the next several years improving his estates and building on the wealth he had gained in the French Wars. In 1381, he seems to have been with the Earl of Warwick in an expedition to London to help put down the Peasants Rebellion, which was effectively over by the time Warwick and his men arrived.

In December of 1387, The Earl of Warwick, one of the “Lords Appellant”, orders Stuart to lead a contingent of men at arms and archers to reinforce Henry of Bolingbroke, the Earl of Derby, who is marching toward London to suppress King Richard’s favorite, Robert de Vere, the Earl of Oxford. While Stuart thinks such an aggressive move unwise, he has no choice but to perform his feudal duty to his lord. While Warwick sends Stuart to battle, he himself does not go. On December 19, the two armies meet at Radcot Bridge [31] on the South Branch of the Thames. The short but hard fought battle ends in a victory for Bolingbroke and the Lords Appellant, but De Vere escapes and remains at large. Sir Stuart is wounded in the right shoulder by an arrow, and returns to Warwickshire to recuperate. Nearing 60, Stuart does not heal well and he loses much of the mobility in his right arm. Moreover, Stuart is increasingly disenchanted with serving a Lord who sends his vassals to battle, but does not go himself. He also comes to believe that his presence at Radcot Bridge will eventually return to haunt him unless he removes himself from the reach of a King he sees as both greedy and vengeful.

In early 1389, Stuart sells his Warwickshire estates, and purchases a large tract of land in the Lochaber region of Scotland. Stuart moves his household and his horses to the new estate, and builds a modest castle-house, where he lives out his days in comparative quiet.

Brittania Biographies. Thomas Beauchamp, 3rd Earl of Warwick. http://www.britannia.com/bios/lords/warwick3tb.html (accessed December 5, 2010).

Castles in Poland. Malbork Castle. http://www.castles.info/poland/malbork/ (accessed December 5, 2010).

Everything2. Battle of Radcot Bridge. 9 6, 2007. http://everything2.com/title/Battle+of+Radcot+Bridge (accessed 12 6, 2010).

La Belle Compagnie . 1381, The Peel Affinity. Harrisburg: Schumacher Publishing, 2007.

Seward, Desmond. The Hundred YEars War, England in France 1337-1453. New York: McMillan, 1978.

Undiscovered Scotland. Edward Balliol. 2000-2010. http://www.undiscoveredscotland.co.uk/usbiography/monarchs/edwardballiol.html (accessed 12 5, 2010).

Warwick, The Countess of. Warwick Castle and it's Earls. London: Hutchinson & Co., 1903.

Wikipedia. Jean III de Grailly, captal de Buch. http://en.wikipedia.org/wiki/Jean_III_de_Grailly,_captal_de_Buch (accessed 12 5, 2010).

—. War of the Two Peters. http://en.wikipedia.org/wiki/War_of_the_Two_Peters (accessed 12 5, 2010).

[1] (Paterson 2001, 25)

[2] (Paterson 2001, 24-26)

[3] (Paterson 2001, 25)

[4] (Undiscovered Scotland 2000-2010)

[5] (Neilands 1990, 107)

[6] (Warwick 1903, 88-98)

[7] (Gravett 2002, 11)

[8] (Ayton 1994, 229,231,241)

[9] (Ayton 1994, 109)

[10] (Ayton 1994, 231)

[11] (Ayton 1994, 128-130)

[12] (Seward 1978, 84-85)

[13] (Burne 1955, 248)

[14] (Nicolle 2004, 12)

[15] (La Belle Compagnie 2007, 119)

[16] (Nicolle 2004, 43)

[17] (Froissart 1968, 126-127)

[18] (Tuchman 1978, 143)

[19] (Neilands 1990, 126)

[20] (Wikipedia n.d.)

[21] (Brittania Biographies n.d.)

[22] (Castles in Poland n.d.)

[23] (Wikipedia n.d.)

[24] (Ayton 1994, 123-127)

[25] (Nicolle 2004, 11)

[26] (Neilands 1990, 164-166)

[27] (Brittania Biographies n.d.)

[28] (Tuchman 1978, 262-263)

[29] (Seward 1978, 111-115)

[30] (Seward 1978, 115)

[31] (Everything2 2007)

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