CHAPTER 8

'Tan graue cosa es veuir omne en tierra de su sennor et auer se a guardar del, commo meter la mano en el fuego e non se quemar.'

Relations between Juan Manuel and his monarch Alfonso XI would remain strained for an extended period. Two major issues, both already known to us, kept them at odds. The first was the matter of Juan's personal security. Having seen the leading aristocrats Juan el tuerto and Alvar Núñez de Osorio dispatched at royal command, the lord of Villena was convinced that he was next on Alfonso XI's death list and could not shake this fear.¹ The second problem was one of honour. Alfonso had wed Juan's daughter Constanza only to later reject her. Until the king made amends for this disgrace, the prospect of a lasting reconciliation was remote.

In the final weeks of 1330 Juan Manuel, no longer distracted with military operations against Granada, sent an embassy to Seville to press Alfonso XI to secure an attractive and worthy marriage for Constanza.² To this end, the king of Castile revived conversations with the Aragonese court about the match between the Infant Pere and Constanza (mooted originally in the summer of 1329). But Alfons IV of Aragon now had other plans for his heir, and stated as much in correspondence of 17 February 1331.³ There were limited other options. A marriage into the Portuguese line was possible. But the king of Castile at that moment was disinclined to engage with his in-laws, for he had recently begun an illicit relationship with a wealthy Sevillian widow by the name of Leonor de Guzmán.⁴

Alfonso XI evidently did not prioritise the finding a marriage for Constanza Manuel over the next few months, for by the summer of 1331 her father Juan had begun a new campaign of destruction against Crown lands.⁵ Such recalcitrance, however, did not provoke any significant reaction from the king of Castile who, keen probably to be with his paramour, remained in Andalusia long beyond the end of the war against Granada. The lord of Villena changed tactics, dispatching that autumn the prior of San Juan, Fernán Rodríguez, to the Portuguese court to flag up the shame which Alfonso XI was bringing upon the House of Portugal with his immoral activities, and to offer Afonso military help against the Crown of Castile in return for his own dynastic marriage. The king of Portugal was amenable to the offer, and a union between Constanza Manuel and the Infante Pedro, heir to the Portuguese throne, was contracted.⁶

On learning of this dangerous alliance, the king of Castile sought to reach an accommodation with Juan Manuel. There must have been conciliatory words or gestures from the latter, for on 27 November Alfonso XI wrote to inform the concejo of Murcia that 'Don Johan fijo del infante Don Manuel mio vassallo e mio Adelantado mayor de la frontera e del regno de Murcia es abenido conmigo et a mio serviçio'.⁷ But there was clearly no sincerity in the lord of Villena’s behaviour, for at that very time his household was covertly negotiating a new military alliance with the king of Granada;⁸ and, remarkably, was taking steps toward the minting of his own currency, presumably both to help finance his military objectives and to highlight his increasing disaffection with the kingdom of Castile.⁹

Alfonso XI’s situation became decidedly worse when the powerful Juan Núñez de Lara, vexed by the refusal of the Crown to cede to him the estates of his late father-in-law Juan el tuerto,¹⁰ joined the international alliance against the House of Castile. Though the political situation in the kingdom at this moment was without doubt particularly tense and precarious, there is no evidence that war broke out. Fernán Sánchez, not one to suppress stories of aristocratic malfeasance, records little beyond Juan Manuel’s push to build new castles and fortify his strongpoints.¹¹ However, since the surviving evidence for this period is sparse, it is very hard to be sure about exactly what went on.

By the autumn of 1332, the unrest remained unresolved. Alfonso XI, it is reported, continued his efforts to placate Juan Manuel, but these were supposedly undermined by the aristocrat Alvar Díaz de Haro, 'que fué decir á Don Joan, quel Rey le mandára que le matase, non seyendo verdad'. This is yet another reported instance (most coming from the Crónica de Alfonso XI) of individuals – usually courtiers – warning Juan that the king of Castile was plotting his assassination. Correspondence from the lord of Villena to the Aragonese court confirms that he had heard this rumour,¹² but we have no way of knowing for sure whether there was any foundation to it. Gautier Dalché declares that 'si le roi de Castille avait voulu obtenir la mort de Don Juan Manuel, il y serait parvenue d'une façon ou d'une autre;¹³ but this is not necessarily true. Given the fates of other leading opponents of Alfonso XI, it seems obvious that this king would have given serious consideration to murdering his unruly kinsman, but that does not mean that every single rumour of such a plot was true. The truth is that there were often individuals within the royal court who did not want to see Alfonso XI and Juan Manuel on good terms, and the easiest way to keep them apart was to sow doubt in the mind of the latter over his personal safety.

Around the close of 1332 Juan Núñez de Lara – assisted by the disaffected courtier Juan Martínez de Leiva and other notables – began to wage war from Lerma on Crown territories.¹⁴ The assault could not have come at a more inopportune time for Alfonso XI, as he had just received three disturbing items of news. First, a powerful Marinid army under Abu Malik, son of the sultan of Morocco Abu'l-Hasan, had just crossed the Straits and established a siege at Gibraltar. Second, the king of Granada’s army was attacking the kingdom of Murcia. And third, Afonso IV of Portugal was readying a force to attack.¹⁵ The Castilian monarch now found himself in a most precarious situation. Arguably he was reaping what he had sown, at last facing the repercussions of his own conduct. His seven years of rule to that point had been punctuated by unscrupulous and often barbarous behaviour, with little care for consequences. Now, many of those whom he had wronged over that period were turned against him. The pivotal figure in this unfolding crisis was, of course, Juan Manuel: Juan Núñez was his brother-in-law, the kings of Portugal and Granada his allies. Alfonso XI was sufficiently astute to recognise that he could very probably temper the enmity of many of his powerful foes simply by improving his relationship with the lord of Villena.

According to the royal chronicle, the young king, cognizant of the fact that Juan Manuel was an avid hunter ('era muy cazador'), sent to him the royal falconer Sancho Martinez:

et envióle decir con él, que quisiese sesegar [Don Joan] en el su servicio; et que fablase con Don Joan Nuñez que feciese aquello mesmo; et que fuesen con el Rey á desercar la villa et el castiello de Gibraltar; et que de todas las cosas que ellos dixiesen, en que el Rey estaba en culpa á Don Joan Nunez, que los emendaria en la manera que Don Joan dixiese que lo debia facer: et que eso de su fija Doña Costanza: et que por esto faria ayuda et merced a Doña Costanza, porque oviese casamiento honrado; et desto que daria rehenes, et les faria seguros por qual manera ellos quisiesen.¹⁶

It is claimed in the same source that Juan Manuel responded positively to this embassy, answering that he would be pleased to return to the service of the Crown and would do what he could to persuade Juan Núñez de Lara to come to terms also, such that they could assist in the liberation of Gibraltar. Tripartite conversations, it appears, took place at Villaumbrales (Palencia). It is reported that Juan Manuel and Juan Núñez asked to be pardoned for past errors and offered to serve their monarch faithfully henceforward 'en guisa que todos los del mundo viesen que ningun Rey nunca fuera tambien mejor servido de tales dos vasallos como él seria dellos'. But, it is alleged, just as the pair were about to put their reconciliation into writing, Juan Martínez de Leiva told Juan Núñez 'que si él et Don Joan fijo del Infante Don Manuel fuesen comer con el Rey en Villumbrales, que fuesen ciertos que el Rey tenia acordado de los mandar matar'.¹⁷ Thus the negotiations collapsed.¹⁸ Once again, Alfonso XI’s brutal reputation had prevented – or been used to prevent – the settling of aristocratic unrest.

In the first weeks of 1333 Alfonso XI received word from the governor of the castle of Gibraltar that 'los Moros afincaban mucho de cada dia la villa de Gibraltar, combatiendola con engeños, et con muy grand poder de ballesteros que el Infante Abomelique tenia y; et que avian comenzado á derribar con los engeños dos torres, et la villa que estaba en afincamiento'.¹⁹ According to one contemporary account, the sultan of Morocco was so confident of success that he had instructed his son Abu Malik 'que no talasse arboles ni viñas, ca tenia que en poco tiempo por toda suya'.²⁰ As reported by a Castilian eye-witness, the inhabitants of Gibraltar could scarcely believe that their king had not yet come to their aid: '[los de la frontera] an tomado tan grand desmayo que se tienen por perdidos todos ca disen que nunca omne oyo desir que Rey de Castiella touiese su logar çercado que sabiendo lo ques non acorriesse'.²¹ Alfonso XI, of course, had delayed his departure to Andalusia because he feared that '[don Joan et don Joan, que] le facian grand daño en la tierra [...] que le farian muy mayor en lo que podiessen desque él allá fuese'.²² If we are to trust the royal chronicle, the king of Castile travelled twice to Peñafiel to persuade Juan Manuel to join the royal army, failing in this endeavour only because 'algunos de los que estaban con el Rey, le enviáran decir [á don Joan] que el Rey lo queria matar'.²³ A familiar story.

By late May 1333, Alfonso XI had secured the involvement of both Juan Manuel and Juan Núñez in the fight against the Muslims, although the lord of Villena – forever concerned about his personal security – was prepared only to wage war on a separate front: from the diocese of Jaén. Alfonso accepted this compromise (in truth, his primary wish was simply that his cousin would not foment unrest in his absence) and around the last days of May the royal host set off for Andalusia.²⁴ The Castilian army arrived in Seville no later than 10 June.²⁵ The assault against Christian property in the South had begun six months earlier and Gibraltar had already fallen, a direct upshot of Alfonso XI’s failure to keep his aristocracy under control. The king of Castile sought to recover Gibraltar, but the Muslims had provisioned the town well and installed and a strong garrison.²⁶ In October he effectively conceded defeat, arranging truces with Abu Malik and the king of Granada.²⁷

Neither Juan Manuel nor Juan Núñez de Lara had made good on their promises to take the fight to the infidel. Instead, they had journeyed to Aragon to present before Alfons IV their grievances against the Alfonso XI. The king of Aragon was able to placate Juan Manuel by declaring Villena (hitherto under Aragonese jurisdiction) a principality, effectively giving it autonomous status.²⁸ But Juan Núñez could not be mollified, and on his return to Castile 'ayunto [en Lerma] todas las mas gentes que pudo aver de malfechores et de encartados, et fué por tierra de Treviño, et dende á Campos robando et tomando todo quanto podia aver'. On top of this, he renounced his vassalage with Alfonso XI.²⁹ The diplomatic energy which the king of Castile had expended through the first half of 1333 had ultimately proven futile. Worse than that, it had cost him Gibraltar.

Alfonso resolved to wage a cruel war against Núñez. Juan Manuel, jaded perhaps by the extended period of political quarrelling, did what he could to quell the enmity between his brother-in-law and the king of Castile. Some time between 16-22 April 1334 he spoke to the former in Peñafiel, convincing him to refrain from attacking Crown property for a period of fifteen days in order to facilitate peace negotiations. And a few days later the lord of Villena met Alfonso XI to discuss the theme of reconciliation.³⁰ The king, however, was intent on subjugating his unruly vassal, and no later than 12 May turned to force, murdering Núñez's powerful friend Juan Alfonso de Haro and establishing sieges at the Laran properties of Lerma and Ferrera.³¹

This outcome was not what Juan Manuel had hoped for, and may have led to new strain in the relationship with his monarch. Around this time the alcalde of Lorca, Pedro Martínez Calvillo, reported to the king of Aragon his suspicion that Alfonso XI had not included Manueline territories in his recent truce with the Muslims, and believed that 'don Joan [...] que non se querra deseretar abra de faser alguna cosa de lo que non querria'.³² Calvillo's doubts, it seemed, were confirmed when on 4 June, Sancho Manuel revealed in a letter to Alfons IV that 'algunos moros nuestros amigos en como el Rey de Granada con todo su poder que viene sobre esta villa [de Lorca]'.³³ Concerned, the king of Aragon pressed his Castilian counterpart on the matter. The latter, at the siege of Lerma, responded reassuringly on 7 July:

Don Joan fijo del infante Don Manuel tiene a Lorca la villa et el castiello es nuestra et tienela por nos como otros nuestros vasallos tienen otras villas et castiellos de nos. Et don Johan es nuestro vassallo et el et toda la su tierra entro en la tregua que nos pusiemos con los moros. Pero nos enbiamos luego nuestras cartas al Rey de Granada et al infante [Abu Malic] sobresto.³⁴

That Juan Manuel was placated by this reply is implied by the royal chronicle, which, never shy to flag up his misdeeds, has no record of him misbehaving through the remainder of the year. Moreover, Alfonso XI would report in a letter to the consejo of Murcia toward the end of 1334 that 'Don Johan fijo del infante Don Manuel nuestro vassallo e nuestro Adelantado maior en la frontera et en el rregno de Murcia es a la nuestra merçed e en nuestro servicio'.³⁵ The chronicle asserts that Alfonso kept Juan Manuel obedient by sanctioning the marriage of Constanza Manuel to the Infante Pedro of Portugal, and there is no reason to disbelieve this.³⁶

By the start of 1335, Alfonso XI's war against Juan Núñez de Lara had run its course. If we are again to trust the opinion of Fernán Sánchez, then Alfonso made a truce with Núñez because 'los de las sus villas [del Rey] estaban en muy grand afincamiento de pobreza por los muchos pechos que avian dado para las guerras que él avia avido con los Moros et con los Christianos del su regno'.³⁷ A more likely factor, perhaps, was that his operations against Laran strongholds were not especially successful and, moreover, becoming a burden on the royal coffers. We may presume from the silence of the royal chronicle that Juan Manuel and his brother-in-law remained obedient for the remainder of this year, although we cannot be completely sure about this due to the puacity of alternative testimony.³⁸

If 1335 was uneventful, the following year was anything but. In early 1336 Afonso IV of Portugal, inflamed by Alfonso XI's reluctance to forswear his extra-marital relationship with Leonor de Guzmán and his refusal to allow Constanza Manuel to travel to marry the Infante Pedro, sent messengers to Juan Manuel, Juan Núñez, Pedro Fernández de Castro and Juan Alfonso de Alburquerque (a high ranking nobleman with close ties to the Portuguese royal house) asking that use their military might to pressure the Castilian king to atone for his misconduct. Juan Manuel agreed to help – no surprise for he must have been as frustrated as the king of Portugal over Alfonso XI's prevarications in respect of the marriage between Pedro and Constanza – and in March he sent his vassal Clemente Sánchez to seek the support of the new king of Aragon, Pere IV, in this endeavour. Pere, predisposed against the Castilian royal family by reason of his poor relationship with his stepmother Leonor of Castile (Alfonso XI's sister), agreed to participate, and on 17 March an alliance of mutual friendship and defence was contracted between the houses of Manuel and Aragon.³⁹ In May, Pere cemented his formal amity with Juan Manuel by conferring upon him the title of 'Duke of Villena'.⁴⁰ On learning of the alliance against him, Alfonso XI established no later than 14 June a new siege at Lerma,⁴¹ and began separate operations against the Laran properties of Busto, Villafranca de Monte de Oca, and Torre de Lobatón. The sheer scale of the operation shocked Juan Alfonso de Alburquerque, part of Afonso IV of Portugal’s alliance, and he defected to Alfonso XI.⁴² Correctly suspecting that Juan Manuel would, this time round, come to the defence of his embattled brother-in-law Juan Núñez, the king of Castile arranged that:

Don Vasco Rodriguez Maestre de Sanctiago, et Don Joan Nuñez Maestre de Calatrava, con mill omes á caballo á costa de las Ordenes, estidiesen fronteros en el castiello de Garci Muñoz et de Alarcon, et de los otros logares que Don Joan avia en esta comarca dó el estaba, et que le vedarian que non levase su fija Doña Costanza á Portogal entre tanto que estaba el Rey en aquella cerca: et otrosí que le non dexarian andar por la tierra á facer guerra.⁴³

Scandalized by this siege, Juan Manuel decided to break his bond of vassalage with Alfonso XI. In a letter dated 30 July to Pere IV of Aragon, he gave his reasons why: the king of Castile had sequestrated his lands; attempted in many deceitful ways to kill him; obstructed the marriage of Constanza Manuel to the Infante Pedro of Portugal; refused to lift the siege of Lerma; treated Queen María dishonourably; and furnished the bastard children of 'aquella mala muger' (Leonor de Guzmán) with lands appropriated from the greater aristocracy. The lord of Villena requested that the Aragonese chancery make a formal record of his renouncing of fealty, for he had decided against sending a vassal to Alfonso XI for this purpose, because 'en Villa real mando matar e cortar las manos e los piedes al escudero que embio don Johan Nunnez a despedirle e denaturarle del'.⁴⁴ For the reign of Alfonso XI, it would difficult to find an activity more dangerous than delivering unwelcome news to the Castilian court.

On 10 August 1336 Alfonso XI, having learnt of his cousin's denaturalization, warned the concejo of Murcia that since:

la su voluntad [de Don Johan] es para faser mal e danno en la tierra [...] que pongades buen rrecabdo en esa villa et que la fagades guardar et asy mismo en las fortalesas que avedes en vuestro termino e que alçedes los ganados e guardedes vuestros terminos e lo al que avedes porque non reçibades danno. Et sy Don Johan et sus compannas fisiesen guerra o mal en la nuestra tierra quel fagades guerra a el e a todo lo suyo la mas crua que podieredes.⁴⁵

Six days later the king of Castile directed Alfonso Fernández de Saavedra, an adelantado in the kingdom of Murcia, to take control of Alhama and Cartagena, properties which Juan Manuel held in benefice by virtue of the adelantamiento of Murcia.⁴⁶

On an uncertain date in August, Juan Manuel, eager to give some support to his brother-in-law Juan Núñez, succeeded in evading the masters of Santiago and Calatrava – who were 'en un lugar que dicen las Chozas, para estar fronteros á Don Joan' – by leaving Garcimuñoz 'por lugares encubiertos'. As soon as Alfonso XI learnt of this, he hurried to Peñafiel, leaving Juan Alfonso de Alburquerque in charge of the siege of Lerma. Juan Manuel, however, could not be persuaded to present battle, and thus the king of Castile repaired to Coriel. Alfonso took his men once more to Peñafiel not long after, but again failed to draw his cousin into battle.⁴⁷ Fearing for his life, Juan Manuel wrote to the king of Aragon soliciting 'homes a cauallo e de ballesteros'. Pere replied before the close of the month that he was assembling a relief army in the kingdom of Valencia.⁴⁸

Alfonso XI seemed to have the upper hand in a conflict that had quickly morphed from an aristocratic rebellion into a fully-fledged Peninsula war. Whilst Pere IV of Aragon was readying a force to attack the king of Castile, Afonso IV of Portugal sent a powerful army against Badajoz and ordered his vassals to wage war against Castilian properties near the Portuguese border. Alfonso XI dispatched a force led by the powerful Galician aristocrat Pedro Fernández de Castro to counter the Portuguese threat. Castro routed the Portuguese army at Villanueva de Barcarrota and managed to raise the siege of Badajoz, but was unable to prevent incursions from Portugal.⁴⁹ Pere IV of Aragon became actively involved in October, sending after the 23^rd of that month a force to battle the Aragonese dissident Pere de Xérica 'et algunos otros que son en conuiniença con el Rey de Castella [...] et puede seer razon quel dito Rey de Castiella se haya de partir del sitio de Lerma'.⁵⁰ But the efforts of Pere’s men cannot have seriously troubled Alfonso XI, for in the late autumn Juan Manuel felt compelled to flee to Aragon, fearing we are told 'que cobraria el Rey la villa de Lerma, et que tomaria á Don Joan Núñez, et que iria luego cercar á Peñafiel, ó do quier que estidiese'.⁵¹ The king of Castile sought immediately to appropriate all Manueline territories in Castile.⁵²

Juan Manuel’s departure was a setback from which Juan Núñez de Lara, trapped in Lerma and likely short of provisions,⁵³ felt he could not recover, and around the close of November he offered to return into the service of Alfonso XI. The king of Castile agreed to receive him into favour on condition that he weaken his strongholds and hand over the castles of Vizcaya as rehenes. Juan Núñez pledged to do this and on 4 December the pair were formally reconciled.⁵⁴

Thereafter, the Lara family sought to negotiate a rapprochement between Alfonso XI and Juan Manuel. Around March 1337 the matriarch Juana Núñez, who had kept in touch with her exiled son-in-law Juan Manuel, wrote to tell Alfonso XI that:

Don Joan fijo del Infante Don Manuel que estaba en Aragon, [...] que queria venir á la su merced del Rey, et que le serviria bien et lealmente dó el quisiese. Et porque el Rey fuese cierto desto, que le daria Don Joan en rehenes la villa et el alcázar de Cartagena, et [...] uno de los castiellos que avia en Peñafiel.

She added that Juan was prepared to allow the Crown to take the abovementioned pledged properties and, moreover, destroy the castles of Peñafiel, Galbe, and three other Manueline forts should he violate the terms of any new peace agreement. Alfonso XI considered this a reasonable arrangement, and in April ratified it.⁵⁵ Juana Núñez communicated this to Juan Manuel and requested that he meet his sovereign. According to the royal chronicle, the ageing Castilian prince, now fifty-six, travelled from Aragon with his wife Blanca to Cuenca for that purpose. 'Et el Rey acogióles muy bien, et fizoles mucha honra, et mostró buen talante á Don Joan, et fabló con el muy bien, de manera que Don Joan fincó bien asosegado en la su merced'.⁵⁶

The long-running dispute between Juan Manuel and Alfonso XI had finally run its course. The kingdom of Castile, as far as we can tell, remained internally relatively tranquil for the remaining years of Alfonso XI's reign. Sánchez-Arcilla Bernal characterised the resolution of this dispute as a triumph of monarchical authority.⁵⁷ Paradoxically, however, it was the misuse of monarchical authority which fuelled in large part the political turmoil of the preceding decade. Modern scholarship often blames Juan Manuel for the interior turmoil of 1327-36 in Castile, but that view is shaped by an over-reliance on the testimony of Alfonso’s hagiographic biographer Fernán Sánchez.

On 3 May, Pere IV of Aragon wrote to congratulate Juan Manuel on his reconciliation. However, Pere was himself now on the edge of war with the king of Castile due to difficulties with the latter's sister Leonor, and so would remind Juan of their political agreement of the previous year: 'quanto mas de bien et de honra ayades tanto mayor conta podremos fazer de vos que creyemos que tendredes bien equello que es puesto entre uos et nos'.⁵⁸ Fatigued by years of conflict, Juan had little desire to see war break out between Castile and Aragon, and no later than 22 July he began work to reconcile the two young kings.⁵⁹ The negotiations were difficult, and it took until the following year to achieve a formal accord.⁶⁰

Precious little is known about the final decade of Juan Manuel's life. It seems probable that he remained broadly obedient over that term. Fernán Sánchez, a zealous documenter of aristocratic misdeeds, is almost silent on him. And Juan’s name consistently appears in the witness lists of royal charters. The little we do know concerns his involvement in two major military campaigns in the South between 1340-44.

In 1338 Alfonso XI was engaged in peace negotiations not just with Aragon but with Portugal also,⁶¹ for there was word that the Banu Marin were planning a new, and large-scale, military operation against Christian property in the South. Pere IV, concerned also by Marinid plans, agreed with Castile a treaty of military cooperation and defence, including the defence of the Strait with their respective fleets (May 1339).⁶² Abu Malik, the Marinid prince in charge of the invasion of Castile, bided his time, deliberately delaying his attack until his full army had been deployed in al-Andalus. In the opening weeks of 1340, the Moroccan prince made his move, dispatching small companies to engage in skirmishes and moving thereafter against Medina Sidonia and Jerez. Malik then took on a Castilian force at Arcos (Seville). His army was routed and he lost his life. The Marinid sultan Abu al-Hasan, father of the slain prince, crossed the Strait to avenge his death, leading a substantial army against the Castilian royal host on the banks of the River Salado near Tarifa.⁶³

According to the testimony of the Crónica de Alfonso XI, Juan Manuel and several other eminent aristocrats leading the Castilian army refused to cross the Salado to engage the enemy. We are told that Alfonso XI sent his naval commander Garci Jufre de Tenorio to find out why:

Et Garci Jufre Tenoyro [...] dixo á este Don Joan, que la espada lobera, que él dicia era de virtud, que mas debia á hacer en aquel dia. Et por lo que el Rey le envió decir, nin por lo que le dixo aquel escudero, Don Juan non quiso facer ninguna cosa, nin acució la pasada: et el su alferez deste Don Johan desque oyó lo que el Rey le enviára decir, et otrosí lo que aquel escudero le dixo, quisiera mover con el pendon para pasar el rio: et Don Joan dióle una mazada que lo oviera á derribar del caballo. Et por esto los de la delantera estidieron que non pasaron el rio.⁶⁴

The authenticity of this story is, of course, difficult to determine. Those disinclined to trust the testimony of Fernán Sánchez would think it quite natural that the royal chronicler should attempt to denigrate Juan Manuel on the grandest stage, and they might note the resemblance between the phrase 'la su espada lobera, que él dicia que era de virtud' and the dying words attributed to Fernando III in El Libro de las Armas – a work to which Sánchez probably had access when composing his chronicles and that was certainly available to later redactors of his original autograph:

Fijo [Manuel], vos sodes el postremer fijo que yo ou de la reyna donna Beatriz, que fue muy santa et muy buena mugier, et se que vos amaua mucho; otrosi [vos amo yo), pero non vos puedo dar heredad ninguna, mas douos la mi espada Lobera, que es cosa de muy grant virtud, et con.que me fizo Dios a.mi mucho [bien].⁶⁵

Anecdotes and hearsay are common in the chronicles of the Castilian kings of this period, and, as we have seen over the course of this account of the political life of Juan Manuel, it is occasionally possible to confirm them with other source material. When we cannot do that, it is incumbent upon us to handle such stories with caution.

At Salado, Alfonso XI and his Christian coalition scored a famous victory over the Muslim invading forces. Fernán Sánchez claims that over two hundred thousand Moors may have been killed at this battle, with Christian fatalities numbering no more than twenty. But these figures seem far-fetched.⁶⁶ Nevertheless, the triumph was genuinely decisive. Never again would the Banu Marin, or any other North African army for that matter, dare to invade the Iberian Peninsula.

Two years later Alfonso XI sought to reconquer Algeciras. Juan Manuel played an active part in the lengthy siege of this strategically important port. Although many Castilians are reported to have deserted, and Juan is not named among them, the royal chronicle still manages to find fault with his conduct, criticizing him (and others) for failing to intervene when two knights were cut down by the Muslims in a skirmish outside his camp.⁶⁷ Alfonso XI seemingly saw no fault in his kinsman's performance at Algeciras, for he bestowed upon the lord of Villena the honour of carrying the Castilian standard into the town upon its surrender.⁶⁸

On Friday 13 June 1348, Juan Manuel, aged sixty-six, breathed his last. He may have died of old age, or possibly of the Plague, which entered the Peninsula through Mediterranean ports during that year and spread rapidly. Juan Manuel’s original biographer Giménez Soler was unable to give a precise date for his death, establishing only that it must have occurred between 10 March and 24 July.⁶⁹ Derek Lomax, however, found the precise date of Juan Manuel's demise in the Kalendar of Uclés, a list of deceased friars and benefactors of the Order of Santiago for the repose of whose souls its members were obliged to pray.⁷⁰

Juan Manuel was buried, in accordance with his wishes, in the Dominican monastery he himself had founded at Peñafiel in 1318. Two of his wills are extant: one produced on 31 May 1339; the other on 14 August 1340 (shortly before he entered into battle with the Marinids near Tarifa). Giménez Soler and Gaibrois de Ballesteros are adamant that the second document is Juan's final will and testament, although it is conceivable that the death in childbirth of the unfortunate Constanza Manuel (1345) might have provoked a further revision. According to the articles of the 1340 will, Juan Manuel's heir Fernando (born seemingly in or close to 1332) inherited the bulk of his father's estate, and his famous 'Lobera' sword. His sister Juana Manuel (whose date of birth is unknown) received Escalona, although with certain pre-nuptial constraints. The illegitimate Sancho Manuel received 50,000 maravedís but no property. No provision was made for Juan Manuel's third wife Blanca. It may be that she had died shortly before the 1340 will was drafted, as provisions concerning her appear in the first will but are absent from the second.⁷¹

Juan Manuel proudly asserted in El Libro de las Armas that his grandfather Fernando III had predicted that 'nunca en este linaje falleciese heredero legítimo'. But Juan’s heir Fernando would die in 1350. The latter’s daughter Blanca (by Juana d’Espina, daughter of Ramón Berenguer of Aragon) would perish in 1360 unmarried, and consequently the line of Manuel was extinguished. Juan Manuel, nevertheless, would have some illustrious descendants. Fernando, the only son of Constanza Manuel and Pedro I of Portugal, succeeded to the Portuguese throne in 1367 as Fernando I. Another grandson, Juan (the son of Juana Manuel and Enrique de Trastamara, eldest of Alfonso XI’s illegitimate sons and later Enrique II) would ascend the Castilian throne in 1379.

It is an abiding irony that Juan Manuel – grandson of the great Fernando III, grandfather of Juan I, and arguably the most eminent Castilian prince of his generation – should have spent so much of his life in conflict with the very bloodline to which he belonged.