Mediterranean Southwest Europe (1360–1371 CE): Dynastic Struggles, Mercenary Warfare, and Literary Advances

The era 1360–1371 CE in Mediterranean Southwest Europe is characterized by intricate dynastic struggles in Granada, the prominent role of mercenary forces in Italy, and significant literary and intellectual developments.

Dynastic Struggles in Granada

Muhammed V of Granada, having initially inherited the throne from Yusuf I, faces turbulent political challenges. Overthrown by his half-brother Ismail II in 1359, Muhammed seeks refuge with the Marinid Sultan of Fez, where he is exposed to influential architectural innovations. Ismail II is quickly overthrown and killed by his brother-in-law Abu Said (Muhammed VI) in 1360. Muhammed V capitalizes on political opportunities, ultimately regaining the throne in 1362 after Muhammed VI is lured to Seville by King Peter I of Castile (Pedro el Cruel) and assassinated. Muhammed V secures diplomatic ties through the marriage of his eldest son, Yusuf II, to the Marinid Sultan’s daughter and completes the construction of an important hospital in Granada in 1366. He employs the renowned scholar and diplomat Ibn Khaldun in negotiations with Pedro the Cruel.

Sir John Hawkwood and Mercenary Warfare in Italy

The cessation of Anglo-French hostilities in 1360 provides an opportunity for Sir John Hawkwood, an English soldier of fortune, to lead his mercenary force, the White Company, into Italy. Hawkwood’s background, obscured by legends, suggests humble beginnings in Essex, with experience gained through service in the early stages of the Hundred Years' War. By the 1360s, Hawkwood commands the White Company, engaging in various military actions across Italy. His forces fight under multiple banners, including those of Milan, Florence, Pisa, Perugia, and the papacy. Notable engagements include battles against the Green Count in Lanzo Torinese, conflicts with Milan, warfare between Pisa and Florence in 1364, and supporting Perugia against Papal forces in 1369. In 1370, Hawkwood aligns with Bernabò Visconti in a conflict involving Pisa, Florence, and other city-states.

Literary and Intellectual Advances: Boccaccio

Giovanni Boccaccio completes a decade-long project, his encyclopedic work On the Genealogy of the Gentile Gods, an influential mythological reference and vigorous defense of poetry. Boccaccio's shift in literary style during this period results from declining health, personal disappointments, and an evolving worldview, partly influenced by interactions with Petrarch. After a crisis of faith in 1362, during which he nearly destroys his literary works, Boccaccio is dissuaded by Petrarch. He retires to Certaldo in 1363, turning from imaginative literature to critical studies, biographies, and geographical works, notably producing the satirical and misogynistic work Il Corbaccio in 1365.

Castilian Civil War

The Castilian civil war from 1366 to 1369 emerges as part of the broader conflict between England and France, the Hundred Years' War. Primarily fought between King Peter I (Pedro el Cruel) and his illegitimate brother Henry of Trastámara, this conflict significantly influences regional politics and involves extensive fighting throughout the Kingdom of Castile and its coastal waters.

Legacy of the Era

The era 1360–1371 CE profoundly impacts Mediterranean Southwest Europe through political upheavals in Granada, the strategic deployment of mercenary forces in Italian warfare, and critical advancements in literature and intellectual thought. Collectively, these developments shape regional dynamics, influencing subsequent cultural, political, and military trajectories

King Peter I of Castile—Peter the Cruel, as he is called by his subjects—abandons and imprisons his wife, arousing the opposition of the nobility led by his illegitimate half brother, Count Henry of Trastamara, who, with Aragonese backing, challenges Peter’s right to rule.

Charles V of France also sends troops into Spain in support of Trastamara, who overthrows Peter.

Peter then turns to English king Edward III, who dispatches an expeditionary force led by his son Edward, the Black Prince.

Edward defeats the Franco-Aragonese-Castilian forces at Nájera in 1367, then departs for England; Trastamara promptly starts a new round of civil war.

Peter of Castile's forces are pitched against those of his half-brother Henry of Trastámara in the civil war of succession in Castile,.

The English crown supports Peter and the French, Henry.

French forces are led by Bertrand du Guesclin, a Breton, who had risen from relatively humble beginnings to prominence as one of France's war leaders.

Charles V has provided a force of twelve thousand, with du Guesclin at their head, to support Trastámara in his invasion of Castile.

Peter appeals to England and Aquitaine's Black Prince for help, but none is forthcoming, forcing Peter into exile in Aquitaine.

The Black Prince had previously agreed to support Peter's claims, but concerns over the terms of the treaty of Brétigny had led him to assist Peter as a representative of Aquitaine, rather than England.

He then leads an Anglo-Gascon army into Castille.

Jean III de Grailly, after his release from imprisonment in 1365, had defected to the French side and had been made lord of Nemours by Charles V of France.

However, he had soon reestablished his loyalty to the English, and in 1367 he goes to Spain with the Black Prince, fighting on April 3 at the Battle of Nájera.

Here he again faces Bertrand du Guesclin, but this time it is du Guesclin who is captured, and the Captal is put in charge of the prisoner.

After Trastámara's army is defeated at the Battle of Nájera, Peter is restored to power.

Olivier de Clisson and the Battle of Nájera (1367)

Olivier de Clisson, a Breton noble and military leader, fought alongside the English under the Black Prince at the Battle of Nájera in 1367, a key engagement in the Castilian Civil War. His forces, under Robert Knolles, faced the French army led by Constable Bertrand du Guesclin, who was captured for the second time after the battle.

The Context: The Castilian Civil War (1366–1369)

• The war was fought between King Peter of Castile ("Peter the Cruel") and his half-brother Henry of Trastámara, who challenged him for the throne.
• Peter of Castile was allied with England under Edward, the Black Prince, while Henry was supported by France and du Guesclin’s forces.
• In April 1367, at Nájera, the Black Prince and his Anglo-Gascon army, supported by Breton and Portuguese contingents, won a decisive victory, briefly restoring Peter to power.

Olivier de Clisson’s Role in Breton Diplomacy (1366)

• Prior to the battle, Olivier de Clisson was sent as an ambassador to Paris in 1366 to ensure that King Charles V of France honored Brittany’s independence.
• Upon his arrival in Paris on May 22, 1366, he was received with great fanfare, reflecting his prominent status in both Brittany and France.
• Despite his diplomatic role, he remained a loyal ally to England in the conflict.

Aftermath and Legacy

• Though victorious at Nájera, the English failed to maintain their influence in Castile, and Peter was ultimately defeated and killed in 1369.
• Olivier de Clisson later changed allegiances, becoming a staunch supporter of France, and was eventually appointed Constable of France in 1380, succeeding his former adversary, du Guesclin.

His dual role as a diplomat and warrior made Olivier de Clisson one of the most influential figures in the Hundred Years’ War, navigating the complex Anglo-French-Breton alliances of the 14th century.

The Moors retake Algeciras from Castile in 1368.

The city is destroyed on the orders of Muhammed V of Granada and will subsequently be abandoned.

The Black Prince’s Taxation Crisis and the Renewal of the Hundred Years’ War (1367–1369)

Following his victory at the Battle of Nájera (1367) during the Castilian Civil War, Edward, the Black Prince, found himself deeply in debt due to the failure of his Castilian ally, King Peter I ("the Cruel"), to provide the promised financial support. Suffering from ill health, Edward returned to Aquitaine, where he imposed a hearth tax to cover his expenses. This unpopular taxation policy alienated his Gascon vassals, leading them to appeal to King Charles V of France, ultimately sparking the renewal of the Hundred Years’ War in 1369.

The Black Prince’s Governance and Financial Troubles

• Since 1362, Edward had ruled Aquitaine in grand style, treating it as an English royal principality rather than a French fief.
• His lavish court and military campaigns placed a severe financial burden on the province.
• The Castilian expedition (1367), though militarily successful, had left him heavily in debt, as King Peter I of Castile had failed to provide the promised funds.

The Hearth Tax and Gascon Resistance

• To pay off his war debts, Edward instituted a hearth tax, requiring every household in Aquitaine to pay a fixed sum.
• This tax was highly unpopular, as it fell heavily on the lower nobility and peasantry, who had already suffered years of war-related hardship.
• Among those who resisted was Arnaud-Amanieu VIII, Lord of Albret, a former supporter of the Black Prince who had grown resentful of the influx of English administrators into Aquitaine.

The Gascon Lords Appeal to Charles V (1368–1369)

• Albret and other discontented Gascon lords refused to allow tax collection in their lands and sought relief from King Charles V of France.
• Charles, known for his legalistic approach to statecraft, declared that:
  • The Treaty of Brétigny (1360) was invalid, as mutual renunciations of suzerainty had never been carried out.
  • Therefore, Aquitaine was still legally a French fief, and Edward was still bound to obey the French Crown.
• Charles V summoned one of the Gascon lords and the Black Prince to Paris to appear before the Parlementand justify their actions.

The Black Prince’s Defiant Response

• In a famous reply, Edward rejected Charles V’s authority, stating that:
  • He would go to Paris with 60,000 men behind him, implying war rather than submission.
• This response gave Charles the pretext he needed to declare Edward a rebellious vassal and to reignite the war.

The Renewal of the Hundred Years’ War (1369)

• Charles V declared war on England, leading to a new phase of the Hundred Years’ War.
• The Gascon lords who had once supported Edward now rebelled, forcing the English to defend their territories in France.
• This conflict would reverse many of England’s territorial gains, marking the beginning of a major French resurgence under Charles V and his military commander Bertrand du Guesclin.

The Black Prince’s harsh taxation policies and defiance of Charles V reignited the war in 1369, leading to the gradual collapse of English rule in Aquitaine and a major turning point in the Hundred Years’ War.

Henry de Trastámara, with the Black Prince gone from Castile, leads a second invasion with French help.

Bertrand du Guesclin had won renown in May, 1364, for winning the battle of Cocherel in Normandy against the opponents of Charles V. Except for this victory, he is unsuccessful in pitched battles, having lost at Auray in 1364 and Nájera in 1367; although eventually celebrated as a symbol of chivalry, he is most successful at such unchivalrous pursuits as brigandage and guerrilla warfare Respected by—and thus able to control—the fierce warriors who are the scourge of the countryside when undisciplined, du Guesclin leads such troops in successfully installing the pro-French Trastamara on the throne of Castile (and León) as Henry II after he defeats his half-brother Peter of Castile and León at Montiel, and murders him on March 23, 1369.

The new Castilian regime will provide naval support to French campaigns against Aquitaine and England.