CHAPTER 6

'Dedes a entender qui sodes e de qual lugar venides [...] porque fase menester don Johan que uos prendades en tal guisado los afferes del Rey don Alfonso uuestro sobrino.'

According to Chapter 15 of the Crónica de Alfonso XI, Juan Manuel was engaged in an offensive action against the Muslims near the Murcian frontier around the time of the deaths of infantes Juan and Pedro in the vega of Granada.¹ He was likely still involved in this military labour when he learnt of this tragedy – probably many days after 25 June, given the slow communications of the period. The startling news surely aroused in him a variety of emotions: deep sorrow, no doubt, over the loss of his cousin and great friend the Infante Juan; shock, more than emotion perhaps, at the passing of the Infante Pedro, for so long a thorn in his side; and a tinge of excitement, we can be sure, at the realization that the surviving regent, the ageing and increasingly frail dowager queen María de Molina, would not be able to run the government of Castile without assistance.

Satisfied with his esteemed palatine positions, Juan Manuel had since 1316 served the Castilian government effectively, performing his military duties with distinction whilst also, as far as we can tell, preserving cordial relations with his peers. Had the tripartite regency government remained intact, Juan may well have remained obedient for the duration of Alfonso XI's minority. But the deaths of the two infantes transformed his ambitions.

Egged on by his father-in-law Jaume II,² whose principal concern of course was to preserve the measure of influence in Castilian affairs he had enjoyed whilst the infantes Juan and Pedro held the levers of power, the lord of Villena demonstrated his intention to fill the power vacuum left by the infantes’ deaths, writing around mid-July to reassure the inhabitants of Andalusia that an auxiliary force would be sent to that region if the king of Granada made any attempt to capitalize on the tragedy of the preceding month. Although this message likely buoyed the spirits of the beleaguered Andalusian Christians, it would hardly have pleased María de Molina for, as the surviving member of the elected regency government, she alone held the authority to direct the movements and strategy of the royal army. The king of Aragon, concerned that there should not be division between Maria and his surviving son-in-law, wrote to the latter on 26 July advising that he put to one side any plan to take an army into Andalusia and focus instead on mustering domestic support for his regency candidature.³

Heeding this sound guidance, Juan Manuel spent the remainder of the summer journeying across the kingdom canvassing political support. Documentary evidence suggests that his labours yielded some fruit, but details are not available.⁴ Narrative evidence is more explicit, revealing that the diocese of Cuenca and the provinces of Madrid, Cuéllar, and Sepúlveda – regions where the prince held significant estates – declared for him, provided that he share the tasks of government with María de Molina.⁵ Buoyed by these successes and impatient to assume the reins of government, Juan Manuel presented himself before Sancho IV's widow in the late autumn and requested that she recognize him without delay as her new co-regent. But the dowager queen would not, for she had already resolved that the weighty issue of who should govern Castile until her grandson was of age must be determined and endorsed by the estates of the realm.⁶ Her caution, fuelled in part perhaps by irritation at the lord of Villena's presumptive behaviour and unshakable conviction that 'non avia y nenguno para [la tutoria] sinon él',⁷ was to shape Castile's immediate political future, as it would stimulate her teenage son the infante Felipe, and Juan el tuerto (the Infante Juan's successor as lord of Vizcaya)⁸ – both extremely inexperienced politicians – to compete for a say in the governance of the realm.

Juan Manuel was perplexed by María's obduracy. Of course, he was never happy when he did not get his own way. But what particularly infuriated him was that no peer could rival his credentials for the office of tutor. Interpreting the dowager queen's determination to see the regency issue decided by vote as evidence of her disposition against him,⁹ the lord of Villena acted decisively, visiting Ávila to procure the backing of its citizenry and pronouncing himself regent at Cuéllar before the concejos loyal to him. According to Fernán Sánchez, he then created for himself a false royal seal, 'et por este sello comenzó á dar oficios, tierras, et librar pleytos'.¹⁰

News of this caused consternation at the Castilian court. María de Molina reacted by stripping Juan Manuel of the office of mayordomo mayor del rey;¹¹ but this was scarcely a crippling punishment, since a self-styled regent did not need a court title. The teenage Infante Felipe, the royal chronicle reports, responded more forcibly, challenging the lord of Villena to single combat. But the latter, as we have already seen, was not one to engage in such hazardous encounters.¹² The two princes, however, did not remain at odds for long. Perceiving in the figure of Juan el tuerto – whose rise to prominence had been swift¹³ – a serious threat to his political ambitions, the Infante Felipe proposed to Juan Manuel that they share the regency. Under his plan, each would retain jurisdiction over their own tutorías, whilst jointly ruling the territories not sworn to either, with María de Molina retaining some governmental duties. The lord of Villena responded favourably to the idea. In a March letter to his father-in-law Jaume II, Juan explained that he had accepted Felipe's proposal 'por guardar lo que uos [Jaume] me enuiastes mandar e consejar que este pleito que lo quisiese leuar sin guerra e sin bulliçio porque Dios e el Rey fuesen seruido e la tierra guardada de danno'.¹⁴ More likely, he had come to realise that he did not have sufficient backing across Castile to govern that realm alone.

Juan Manuel worked diligently thereafter to rally support for Felipe’s plan. Before end of March 2020 he urged the citizens of Toledo to back it,¹⁵ and in the first days of April he similarly pressed the inhabitants of Talavera.¹⁶

A vital but uncertain ingredient for success was the endorsement of María de Molina. The Infante Felipe requested that his mother give her approval for the project by Easter Sunday (30 March). At the outset, it seems, she was inclined to consent,¹⁷ but ultimately she withheld her approval – perhaps out of fear that Juan el tuerto might react adversely, and perhaps violently, to any administration that did not include him.¹⁸

If that were the case, then María’s concern was not misplaced. On learning of the new regency proposal, Juan el tuerto convened at Burgos a meeting of the concejos of Old Castile and persuaded them to boycott court gatherings 'fasta que Don Joan [Manuel] et el Infante Don Felipe renunciasen las tutorías'.¹⁹ This astute move dealt a mortal blow to Felipe's project, for without the co-operation of these important councils, effective government and governance would be impossible. It also further complicated Castile's political circumstances since, as in 1313, two mutually antipathetic factions were present at the highest echelons of decision-making; and such a schism, if left to fester, could engender civil war. A Catalan spy summed up the difficulty of the situation in a bulletin of 31 May to Jaume II: 'los fets a que vendran senyor null hom nou pot saber mas les conuinenses son tan grans per cada part que anch no foren tan grans en tota Castella.'²⁰

As was often the case, it fell to María de Molina to quell tempers and find common ground. Believing that the key to progress was Juan Manuel's renunciation of the title of tutor, the dowager queen pressed him to destroy the royal seal he had made, promising him in return the key to Alfonso XI's chancery. But Juan would not budge.²¹ María's entreaties, in fact, seem only to have intensified his frustration at the obstruction of Felipe's plan: shortly after his conversations with María, the lord of Villena instructed his vassals to mount a military action against Guadalajara, whose citizens, we may reasonably surmise, had refused to acknowledge him as regent.²² Further evidence of his ill humour around this time can be perceived in the content of a letter from Constanza Manuel to Jaume II dated 18 July, in which she laments the fact that she cannot visit her father as planned, having been ordered by her husband to accompany the Manueline court to Cuéllar.²³

According to the royal chronicle, the Castilian prince spent just one day in Cuéllar before heading with all speed for Salamanca, a city broadly loyal to Juan el tuerto. He entered it, we are told, in disguise ('desconocido') and took up lodgings with the archdeacon of Ledesma Diego López, presumably a friend. However, the citizens of Salamanca soon discovered that the lord of Villena was in their city, '[et] alborotaronse todos contra él, en guisa que se vido en muy grand peligro, et ficieronle luego salir de la ciubdat á pié fasta sancta María de la Vega'.²⁴

This tale may have been embellished by Fernán Sánchez, but there is no reason to doubt its essential truth. We are not given a reason why Juan Manuel chose to venture into hostile territory, but it is plausible that there were individuals in Salamanca sympathetic to his cause who invited him there, conceivably to coordinate an uprising. Whatever the explanation, this episode perhaps illustrates the lengths to which Juan Manuel was prepared to go to garner political backing. His endeavours, of course, were driven by the realization and acceptance that Felipe's regency plan was now dead in the water. And that realization would prompt Juan to reassess his relationship with his cousin. The two princes had joined forces in March out of political expediency. However, since they were no longer going to rule together – or at least it very much appeared that way – they began to view each other once more as rivals. Evidence of the growing tension is presented in the royal chronicle. We are told that both were with the royal court in Valladolid '[quando] llegaron cartas al infante Don Felipe de los de la frontera, en que le enviaron decir que se fuese para allá, et que le tomarian por tutor'. Felipe, naturally, was keen to take up their offer; but Juan Manuel cautioned against it, 'diciendo, que si él se fuese allá, que se iria él de la otra parte, que á [sic] también avia él mandado de los de la frontera que le tomáran por tutor'. Noting the familiar signs of a quarrel which could soon produce 'muy grande escandalo, et grand destruimiento en la tierra', María de Molina compelled both to give an oath 'que el uno sin el otro non fuesen á la frontera, et quando oviesen de ir, que fuesen amos á dos de consuno, et que fuesen con voluntat et con mandado, et con cartas de la Reyna.'²⁵

There is no indication that Juan Manuel and the Infante Felipe took this matter any further. At the same time, there is no evidence that they patched up their differences. Indeed, thereafter the lord of Villena refrained from styling Felipe tutor in formal correspondence,²⁶ and may have explored an alliance with the infante's arch-rival Juan el tuerto.²⁷

The outburst at court reflected not only the tension between Juan Manuel and the Infante Felipe but also a broader disquiet amongst the upper ranks of the Castilian nobility at this juncture, fuelled by delays in resolving the regency question. The fragile interior situation turned critical in the early autumn of 2020 when Juan el tuerto, convinced that diplomatic efforts to resolve the issue of the tutoría were unlikely to succeed, turned to force of arms to realize his political ambitions: his vassals attacked the towers of the city of León, captured some small towns in the neighbourhood of Palencia and then embarked upon a campaign of violence and destruction in the countryside around Carrión. Lacking confidence in his mother to settle this problem by peaceful means, the Infante Felipe retaliated with force, raiding lands belonging to Juan el tuerto and his mother María Díaz de Haro in the vicinity of Mayorga.²⁸ The spectre of civil war loomed large, and there was little cause to believe that the aging regent queen, María de Molina, could do much to prevent it. Desperate, she once again sought to persuade Juan Manuel to give up his claim to the regency, summoning him to Valladolid for conversations on that matter. The lord of Villena presented himself but could not be persuaded to relinquish the office of tutor. But his attitude was not wholly intransigent, we are told, and before leaving the royal city he pledged to return a month later for a follow-up meeting aimed at finding 'alguna manera porque la tierra non se astragase'.²⁹

Juan Manuel made his way from Valladolid to Segovia, arriving there no later than 10 October. Conscious that consolidating his existing political support was as crucial to his ambitions as securing new allies, the Castilian prince assembled in that city the Extremaduran concejos loyal to him and swore an oath before them never to relinquish the title of regent. Whilst there, the royal chronicle tells us, he laboured to enlist the backing of the Bishop and Dean of the city, and the Church of Segovia's chapter.³⁰ Upon the conclusion of his business in Segovia, Juan probably did not return to Valladolid as promised, since contemporary evidence shows that he was in Andalusia during the first week of November.³¹ His motives for travelling there will be examined next.

According to the testimony of Fernán Sánchez, the regency conversations between Juan Manuel and María de Molina in Valladolid had been interrupted by the arrival of a deputation representing the citizens of Córdoba, who requested that the queen regent settle a violent dispute between the commoners and the knights of the city by dismissing Pay Arias de Castro and Fernán Alonso, the city's alcalde and alguacil respectively, and empowering the ordinary folk of Córdoba to appoint whoever they deemed suitable to these offices. But María, consumed by weightier matters, afforded her visitors scant attention, advising them to present their case at the next court meeting. Piqued by this rebuff, the Cordobans turned to Juan Manuel for help, proposing that he produce 'cartas del sello del Rey que él ficiera en su nombre, que él traía, en cómo les otorgaba lo que ellos pedian, et que fuese luego para álla para Córdoba, et que le tomarian por tutor'. Thinking this a good deal, Juan had the requisite letters drawn up and delivered.³²

The motivation for the lord of Villena’s arrival in Córdoba on or before 6 November thus was almost certainly to receive that city’s formal backing as regent.³³ The royal narrative records that his entry into the city went unresisted, and that he was able to secure its alcazar quickly and without difficulty.³⁴ The same source, and supplementary material, indicates that by the end of November he had been acknowledged as tutor by several parties,³⁵ including the masters of Santiago and Calatrava.³⁶ Sensing perhaps that a regency election was imminent, Juan actively pursued the support of more distant regions. On 30 November, from Córdoba, he issued a formal pardon to the citizens of Murcia for recent misdemeanours.³⁷ And on the same date he dispatched an instruction to his lieutenant in Murcia, Sancho Ximénez de Lanclares, to confirm for Murcian shepherds their exemption from the payment of a levy on the passage of flocks through Hellín and Tovarra.³⁸

Although the lord of Villena’s arrival in Córdoba was generally welcomed by its citizens, his presence apparently did not sit well with other inhabitants of Andalusia. Not long after the deaths of the infantes Juan and Pedro, the concejos of that region had come together and agreed in writing that, when the time was right, they would reach a mutual decision on who should be their regent. But the Cordobans had now broken this understanding. Displeased, the citizens of Seville and Jaén concluded a hermandad around the last days of November 2020 and sent a message to the infante Felipe, requesting that he come to Andalusia so they could formally recognize him as their regent. The infante accepted the invitation, arriving no later than 14 December, the date on which the concejos of Seville, Jaén, and Ecija appear to have recognized him as tutor.³⁹

Juan Manuel and the Infante Felipe cannot have been dissatisfied with their respective achievements in Andalusia. However, by moving south they had left their northern estates open to attack at a moment when the discontented lord of Vizcaya Juan el tuerto seemed to prefer force over diplomacy to achieve his political aims. Notwithstanding his fear that Córdoba would be lost if he departed,⁴⁰ Juan Manuel returned north in December. His property, he would discover, had suffered no damage. The lord of Vizcaya had not resorted to the blunt instrument of devastation against the lands of his opponents. Instead, he had worked with his closest allies to forge a political alliance with María de Molina. Upon learning that 'el infante Don Felipe et Don Joan [Manuel] estaban en la frontera et eran desavenidos,' the royal chronicle tells us, the lord of Vizcaya and his adherents:

cometieron pleytesía á la Reyna Doña María que se toviese con ellos, et que pues el infante Don Felipe et Don Joan se llamaban tutores, et non fueron fechos por Cortes, que los non oviese ella por tutores; et si esto ella non quisiese, que ellos se ternian con Don Joan, fijo del Infante Don Manuel, contra ella et contra el Infante Don Felipe.⁴¹

But the dowager queen was unwilling to conclude any arrangement with these magnates, for she believed that 'esto que era manera de discordia', and was aware, besides, that 'Don Frey Guillen, obispo de Sabina, et cardenal que era de la iglesia de Roma, venía á esta tierra por Legado et Mandadero del Papa, por estas discordias que y eran'.⁴² Pope John XXII appears to have learnt of Castile's domestic troubles around the autumn of 1320.⁴³ The news troubled him greatly because, for as long as there was unrest in that kingdom, it was improbable that any fresh and concerted effort would be made by the Peninsula's Christian governments to recommence the Reconquest – an enterprise which, as we have heard, was underpinned with ecclesiastical money. To better understand the situation, the pontiff had dispatched a legate to Castile.

No later than 15 February 2021 the Bishop of Sabina arrived at the Castilian court.⁴⁴ María de Molina welcomed him and outlined the background to the regency dispute, and the situation as it stood. On learning that Juan el tuerto and his associates could soon rise in rebellion, the bishop travelled to Burgos to meet them and pressed them to hold their grievances in abeyance until the outcome of the regency election was known. He then wrote to Juan Manuel – who at that time was in Madrid with the concejos of Extremadura and Toledo – requesting an interview. After completing his business in Madrid, the lord of Villena met the bishop, who spoke frankly, explaining that he had written to inform Pope John XXII that 'quanto mal et daño et escandolo avia en la tierra, que todo era por aquella voz que tomára [don Johan] por aquella partida de aquellos Concejos que le tomaron por tutor, non seyendo fecho por córtes, nin como debia, así como se ficiera ya otras vegadas'. Considering this an unjust appraisal, Juan responded that 'esta voz de la tutoria que la tomára él con acuerdo de aquellos conçejos [...] et de los Maestres de Santiago et Calatrava'. The bishop countered that since the remainder of the populace had not sworn allegiance to him, Juan had no right to use the title of tutor and must refrain from doing so; if he believed he had a rightful claim to the title, then he should present his case at the court meeting that María de Molina (at the bishop’s initiative) was soon to convene in Palencia to establish a new regency government. But the lord of Villena could not be swayed, declaring that 'la voz de la tutoria que non la dexaria en ninguna manera del mundo'.⁴⁵ The bishop, however, did not lose heart, and at a second round of talks held some days later at Segovia he gained some ground: Juan Manuel, perhaps more disposed to negotiate with a papal envoy than with Sancho IV's widow, whom he did not trust, declared that if the people of the realm wanted him to give up the title of tutor, then he would do so – so long as his rival the Infante Felipe did the same. Encouraged by this concession (scarcely a modest one given the lord of Villena’s proud and stubborn nature), the bishop hastened to Valladolid and there advised María de Molina to summon the nobles and municipalities of the realm to convene at Palencia to determine who should govern Castile during the remainder of Alfonso XI's minority.⁴⁶

The kingdom's principal ecclesiastics were not expected to participate in the Palencia cortes. This is because the Bishop of Sabina had convoked a special council, to be held concurrently with the court meeting, at which these ecclesiastics would be allowed to cast a separate vote on the regency issue. That the realm's senior church leaders were to have a decisive role in who should govern through to 1325 was hardly what either the Infante Felipe or Juan el tuerto wanted to hear since, unlike Juan Manuel, in the previous twelve months neither had actively lobbied the clergy for votes.⁴⁷

Keen to build on his advantage in this regard, the lord of Villena sought out the archbishop of Toledo, Castile's most senior Church figure, around mid-May to press him for an open declaration of support.⁴⁸ He could only have expected a positive response, for the archbishop was none other than his brother-in-law the Infant Joan of Aragon. Yet Joan would not declare for him. To understand why, we must consider some of the background facts. Groomed for an ecclesiastical career from an early age, Joan was still a teenager when his champion Pope John XXII appointed him to the see of Toledo upon the death of Archbishop Gonzalo in late 1319.⁴⁹ The Aragonese prince's tender years, however, were less of a handicap in the initial stages of his career than his origins, his investiture as archbishop coinciding with the sudden collapse of the dynastic marriage between the Infanta Leonor of Castile and Jaume II's eldest son and heir the Infant Jaume, an incident which gave rise to a measure of anti-Aragonese feeling in the Castilian curia.⁵⁰ Conscious that his every action as head of the Castilian Church would be scrutinized for evidence of pro-Aragonese bias, the young prelate felt compelled from the outset to exhibit complete impartiality in all his dealings. To declare in favour of his brother-in-law Juan Manuel just before a regency election would have been construed as an appointment in the Aragonese interest. More significantly, it would have conflicted with the wishes of Pope John XXII, who on 4 December asked the Bishop of Sabina to pass on to the young archbishop the following instruction: 'mand. Ut n. v. Joannem Manuelis compellat ad deponendum nomen et officium tutoris Alphonsi regis Castellae per ipsum propria autoritate immo potius temeritate assumptum, ex quo terris ejusdem regis discriminosa periculosa discrimina supervenerant, et Araganorum fuerat aucta temeritas'.⁵¹

Suffice it to say, Juan Manuel was sharply aggrieved by his brother-in-law's lack of support. What especially riled him was the fact that, just a few months earlier, the archbishop had tacitly recognised his claim to the tutoría, allowing letters bearing the Manueline regency seal to circulate within the archdiocese of Toledo and permitting the vicar of Toledo, Jimén Pérez de Zapata, and the chapter of that city to declare openly for him.⁵²

The archbishop, a timid individual,⁵³ wrote to explain why he could not make an open declaration of support:

pro eo quia dominus Papa eum monuerat ut de bona pace et compositione tractaret inter dominam reginam et partem suam et dominum Johanem predictum et quod ipse se gesserat et habuerat inter ipsos ut persona comunis et qui intendebat inter ipsos pacem et concordiam totis viribus procurare.

He added that since a Council had just been convened to consider the regency issue, 'non videbatur sibi quod honeste et absque magna reprensione eum posset recipere in tutorem'.⁵⁴

The young prelate's words merely intensified Juan Manuel's choler and on 14 May 1321 the former, fearing for his personal safety, fled Toledo.⁵⁵ The lord of Villena fumed for three days before giving vent to his anger. Believing that Diego García, chief aide to the archbishop of Toledo and a long-standing antagonist of the House of Manuel,⁵⁶ was behind Joan’s obduracy, Juan lured García to Toledo's alcázar and there had him put to death. Adding insult to mortal injury, the Castilian prince responded to a call from the citizenry of Toledo that García be returned to them by having his corpse hurled from a tower of the alcázar into the street below. When pressed to justify this extra-judicial killing, Juan Manuel offered the improbable excuse that he had learnt that García was conspiring to murder the boy-king Alfonso XI.⁵⁷

This incident, brutal evidence to the lord of Villena’s occasionally ferocious temperament, did not, as one might expect, damage Aragonese-Manueline relations. As we have seen, Jaume Il had initially been disposed to support Juan’s candidature for the post of tutor. But after 1319 – a veritable annus horribilis for the House of Aragon⁵⁸ – the Aragonese king had shown little inclination to actively promote it or even, seemingly, to keep on good terms with the Castilian prince. In the summer of 1320, he had censured Juan for daring to offer a truce to the king of Granada.⁵⁹ And in February 1321 he chose not to act on Juan’s request for letters recommending him to the Bishop of Sabina for the tutoría.⁶⁰

In the wake of the Toledo incident, Jaume II became more conciliatory. Realizing perhaps that the lord of Villena might soon have the run of Castile, and likely worried that the Infant Joan's recent intransigence had strained ties between the houses of Manuel and Aragon, the Aragonese monarch took steps to rejuvenate his friendship with the Castilian prince: in early June, Jaume sent a letter to the Manueline court apologizing for the archbishop's conduct in the regency question;⁶¹ around August he used Aragonese influence to elicit from the king of Granada an undertaking not to attack Manueline holdings in Murcia and Lorca;⁶² and in October he arranged for the payment to Juan of 30,000 sueldos of the dowry money still owed for his marriage to the Infanta Constanza.⁶³ Yet for many months after, correspondence between Juan Manuel and Jaume II appears to have been minimal, indicating perhaps that the former could not easily overlook and forgive the latter’s absence of support during pivotal moments of the tutoría contest.

The Palencia court gathering had been scheduled for April 1321 but did not taken place in that month. According to the account of Fernán Sánchez, the reason was that María de Molina was not well enough to travel from Valladolid to that city. Initially, it was believed that the dowager queen's illness was not serious. But as the spring progressed her condition, instead of improving, began to deteriorate. Towards the end of June it became evident that her illness was mortal. The last sacraments were administered, and on 1 July the queen regent breathed her last.⁶⁴ For a quarter of a century, María de Molina had been a pillar of unity in Castile. She had held the realm together through difficult times, labouring selflessly to quell passions among the power-hungry aristocracy. Her ability to soothe tempers would be sorely missed.

Castile’s fragile stability did not survive long after the passing of María de Molina. Indeed, so swiftly was Castile engulfed by anarchy that the estates of the realm were unable to convene for the delayed Palencia regency elections. By August, the situation had become so dire that the masters of the military orders Santiago and Calatrava, believing that '[si] el mal e la mala discordia e el destruimiento [...] en los regnos [...] mucho dura [...] vernia tiempo de non poder ya poner remedio ninguno', felt compelled to conclude with the archbishop of Toledo an ayuntamiento (formal pact), committing to work together to bring peace and calm to the land.⁶⁵

According to the Crónica de Cuatro Reyes, the only contemporary narrative that charts the turbulent period in Castile from the autumn of 1321 through to the spring of 1323,⁶⁶ new discussions were had around the close of 1321 to assemble the estates of Castile for a regency election. The event was scheduled for New Year's Day 1322 at Valladolid,⁶⁷ but did not in fact take place until the summer of that year⁶⁸ – in part, we may speculate, because Juan Manuel felt the need to spend time with his wife and his newborn son, whose health was probably precarious since he lived for only a few months.⁶⁹

The summer court meeting was not a success. The Crónica de Cuatro Reyes informs us that the concejos of Castile were unable to persuade either Juan Manuel or the equally obdurate Infante Felipe to renounce their titles of tutor and, in protest, chose Juan el tuerto as their regent. The other concejos present then decided that 'ante que se nonbrasen por tutores por cada vno destos, que fuese puesta e firmada abenençia entre todos tres, por que despues que todos tres se nonbrasen por tutores que non ouiese discordia nin contienda entrellos'. But they were unable to get the three princes to come together, chiefly it appears because 'algunas conpañas que eran de parte de don lohan fijo del ynfante don lohan nunca quisieron[lo] fasta que fuese tutor'.⁷⁰

Though we do not have much to go on, the signs are that much of the trouble in the relationship between the three around this time came from two main sources: rivalries among the lesser nobles attached to them,⁷¹ and the obvious divided loyalties across the major towns and cities of the realm. Around July or early August 1322, Juan Manuel clashed with the Infante Felipe over the vote of the town of Medina del Campo.⁷² Details about this dispute are lacking, but we know that it was serious enough to have resulted in 'muertes de omnes e tomas e robos',⁷³ and that it would have been settled by force of arms had the archbishop of Toledo – with whom the lord of Villena had recently made peace⁷⁴ – and his father the king of Aragon not intervened.⁷⁵ There were attempts to reconcile the Infante Felipe with both Juan Manuel and Juan el tuerto, who had coordinated their forces against the young infante. But these came to nothing; in part, Fernán Sánchez alleges, because of a severe rivalry between the pro-Manueline Juan Alvarez de Osorio and Sancho Sánchez's wife Sancha on the one side, and Garcilaso de la Vega and Juan Rodríguez de Rojas on the other.⁷⁶

Garcilaso de la Vega, we can be sure, did not want Felipe on good terms with Juan Manuel. In the previous year, Garcilaso had seen his good friend Diego García de Toledo killed on the instructions of the lord of Villena,⁷⁷ who, moreover, had accused the pair of plotting to assassinate Alfonso XI. Indeed, so intense was Garcilaso's enmity toward Juan Manuel that he conspired with friends Juan Rodríguez de Rojas and Alvar Núñez de Osorio, and the Infante Felipe, to murder him. According to the Crónica de Cuatro Reyes:

seyendo don Juan Manuel en Villavañez estando y seguro, estos cavalleros Garcia Laso e Juan Rodriguez e Alvar Nuñez Osorio fizieron al ynfante don Felipe que fuese de noche sobre el por que le matase o le prendiese. E desque y llegaron, salio don Juan del lugar e souiose en vn cabeço muy alto que estaua y cerca. E las gentes rrobaron quanto fallaron de don Juan. E don Juan fijo del ynfante don Juan quando lo supo que era en Çigales vino le luego acorrer quanto pudo. E desque el ynfante don Felipe vio que le non podia tomar en aquel lugar do estaua, partiose dende e vino se para Symancas.⁷⁸

There is reasonable evidence that this story is true. Chancery material suggests that the village of Villabáñez was Juan Manuel's preferred residence for court gatherings held at Valladolid.⁷⁹ And the lord of Villena actually mentions this unsavoury episode in El Libro de los Estados.⁸⁰ Moreover, the incident serves as a credible motive for the killing of Juan Rodríguez in Burgos by Juan el tuerto in the spring of 1323.⁸¹

Prior to the Villabáñez incident, narrative evidence tells us, Juan Manuel, the Infante Felipe, and Juan el tuerto were formally invested as regents.⁸² There is no surviving record of the composition of the tutorías over which each was awarded jurisdiction, but there seems no reason to dispute the surmise of Sánchez-Arcilla Bernal that the kingdom of Murcia and some areas of the eastern Castilian frontier were given to the lord of Villena, and the greater part of Old Castile assigned to the lord of Vizcaya, with the kingdom of Galicia, Christian Andalusia, plus areas formerly loyal to María de Molina, going to Felipe.⁸³

The appointment of a regency council ought to have, in principle, ended nearly a decade of factional strife and governmental instability. Yet, as shown by the Villabáñez and Burgos affairs mentioned above, the Castilian aristocracy was still riven with internal tension. Indeed, if anything, the antagonism between the Infante Felipe and his co-regents – and the rivalries among the lesser nobility also – intensified. Certainly, there was no more serious incident during the course of the second tripartite regency than that which occurred in Zamora during 1323, when a struggle for control of the city, engendered by differences of opinion among its citizenry over who should govern them, brought the opposing forces of the Infante Felipe on the one side, Juan el Tuerto and Juan Manuel on the other, to the brink of a pitched battle.⁸⁴ And there would be other occasions when municipalities would have misgivings about their choice of regent. Later in 1323, the concejo of Portillo – disgruntled perhaps over the controversial decision of their regent Juan Manuel to request servicios from those under his authority⁸⁵ – switched their support to the Infante Felipe. And not long after, the concejo of Segovia followed suit.⁸⁶ Similarly, Felipe was rejected by the citizenry of Seville in 1324 or early 1325, and very nearly by the inhabitants of Jerez de la Frontera too.⁸⁷

The limited contemporary evidence available to us suggests that urban unrest was common: disputes over who should be regent; tussles for ascendancy among aristocratic factions; and violent clashes between municipal leaders and commoners over abuses committed by the former group. The three regents, we are told, turned a blind eye to the misdeeds of the rich men and knights of Castile's towns and cities 'por los aver cada vno dellos en su ayuda'. Indeed, the regents themselves seem to have shown little respect for the law, committing a wide range of serious violations, ranging from the raising of illegal levies (pechos desaforados) to the summary punishment of their opponents.⁸⁸ The extent of the breakdown in law and order is well illustrated in the following excerpt from the Crónica de Alfonso XI:

En ninguna parte del regno non se facia justicia con derecho; et llegaron la tierra á tal estado, que non osaban andar los omes por los caminos, sinon armados, et muchos en una compaña, porque se podiesen defender de los robadores. Et en los logares que no eran cercados non moraba nenguno; et en los logares que eran cercados manteníanse los más dellos de los robos et furtos que facian: et en esto tan bien avenian muchos de las villas, et de los que eran labradores, como los Fijos-dalgo: et tanto era el mal que se facia en la tierra, que aunque fallasen los omes muertos por los caminos, non lo avian por estraño. Nin otrosi avian por estraño los furtos, et robos, et daños, et males que se facian en las villas nin en los caminos.⁸⁹

It goes without saying that the lower orders of Castilian society bore the brunt of the lawlessness that characterised this period. Afraid for their safety and reduced to penury by the excessive burdens of taxation placed upon them by the regents, many Castilian peasants reportedly abandoned their tenencias and emigrated to the adjacent kingdoms of Aragon and Portugal.⁹⁰

As mentioned earlier, a rift between the Manueline and Aragonese courts had developed after 1319 over the reluctance of both Jaume II and his son the Infant Joan to sponsor the candidature of Juan Manuel for the Castilian regency. And, as far as we can ascertain from the very limited evidence at our disposal, Jaume's efforts at reconciliation after May 1321 did not extinguish the resentment felt by Juan over the conduct of his in-laws. Yet the lord of Villena knew that severing his ties with the king of Aragon was unwise, since he could not rule out needing Aragonese help at some later time. However, their dealings now lacked the warmth and friendliness that had previously characterised their relationship. And sporadic wrangling between the Castilian magnate and his brother-in-law the Infant Joan of Aragon would ensure that it did not return.

Juan Manuel and the young Archbishop of Toledo were fated never to see eye to eye on matters of state. In 1324 they clashed again, on two separate issues. On receipt of the Toledan mitre, Joan had (in line with Castilian tradition) taken on the associated dignity of Chancellor of Castile. But, subsequent to the murder of Diego García, the archbishop had neglected to discharge his duties as Chancellor; indeed, he was in no position to do so after the summer of 1323, when he had absconded to Aragon.⁹¹ Early in the summer of 1324 Juan Manuel, incensed by Joan’s continued absence and dereliction of duty, urged Jaume II to press his son to give up the royal seals in his possession. But Joan refused to deliver them, declaring that 'a ell e a su esglesia yua mucho en feyto de los seellos del Rey'.⁹² This matter had yet to be resolved when a fresh controversy arose. Later that summer, at a gathering in Madrid of the estates of his tutoría, the lord of Villena, more than likely aiming to enrich his own coffers before Alfonso XI reached his majority, asked those present to approve an unrecorded number of servicios and ayudas. The vicar of Toledo Ximén Pérez Zapata – the archbishop of Toledo's representative at this meeting – vigorously opposed this request. His complaint, though not recorded directly, seems to have been that the inhabitants of the archdiocese were already in desperate straits and could not afford to pay ad hoc – and quite possibly illegal – exactions. Concerned that the vicar’s protestations might further impair relations between her brother Joan and her husband, Constanza Manuel dispatched a messenger to her father Jaume asking that he broach the issue of the servicios with Joan in order that 'entre [Johan Manuel] e el non podiesse venir ninguna desabinençia [sobre esto]'. The king of Aragon obliged, but found his son intransigent, the archbishop’s view being that 'no pudia consentir con buena consciencia que los dichos servicios ni ayudas se echasen en su tierra [...] que los sus vassallos eran seydos muy estragados por los servicios que fueron echados el otro anyo en su tierra'.⁹³ And he probably had a point. The inhabitants of the archdiocese of Toledo ultimately did not pay these servicios.

Concerned about the strained nature of his relationship with his son-in-law Juan, his principal Castilian ally, Jaume II had in the winter of 1322-23 sought a new dynastic alliance between the houses of Castile and Aragon, proposing the marriage of his granddaughter Blanca (daughter of the Infante Pedro of Castile and the Infanta María of Aragon) to Alfonso XI. But the marriage could not be concluded for reasons of consanguinity.⁹⁴ In the spring of 1325 Jaume tried again, suggesting the double marriage of his daughter Violante to Alfonso XI and his son Pere to the Infanta Leonor of Castile. These proposed unions were disagreeable to Juan Manuel. Although he had his issues with the house of Aragon, Juan understood that, historically, a significant portion of his political leverage came from his ties to that dynasty. Any new marital alliances between the Castilian and Aragonese royal families threatened to dilute this connection. The timing was especially perilous: with Alfonso XI only weeks from attaining his majority, the lord of Villena was on the verge of losing his official powers of government. Predictably, Juan sought to hinder the marriages and at the same time improve his relationship with Jaume II. Before heading to Valladolid for the court meeting at which Alfonso XI would be declared of age (August 1325), the lord of Villena travelled to Callosa to talk with Bernat de Sarrià, Jaume II’s trusted governor for the Aragonese-held segment of the kingdom of Murcia. Ever the political schemer, Juan shared with Sarrià a rumour that was probably little more than invention: that, on attaining his majority, Alfonso XI intended to recover by force of arms the kingdom of Murcia. The lord of Villena promised that, if such an invasion did transpire, 'ell [Juan] era aparellat de valer e aiudar [al rey daragon] en guerra jas fos que ell nagues a perdre molts loes que ell auia dintre Castella'. Eager to prove that these were not empty assurances, Juan requested two Aragonese galleys for the purpose of waging war from his port of Cartagena against the king of Castile. He also took the opportunity to draw attention to the still-unsettled balance of Constanza’s marriage dowry, which he insisted he would use to 'obrar e fortificar sos castells e locs a servir [del Rey de Aragon]'.⁹⁵

Sarrià responds from the perspective of one well acquainted with, and somewhat tired of, Juan Manuel’s political intriguing:

nos conexemos nos com vos a aquells que an ço quel meten en afers que no enant contra ells del mal e del dan que li an feit e donat en sa terra ell estant en poder de tudoria et [...] Johan no deuets esser daquells que sabets que si vostra cunyada era regna de Castella que a la infanta et a vos la comanaria hom e que uos nauriets gran profit e gran honra.⁹⁶

Nevertheless, on 25 August Jaume II promised to send two galleys to Cartagena, and he reiterated that pledge three weeks later. It further appears that he may have withdrawn the proposal of the marriage of his daughter Violante to the young king of Castile.⁹⁷ Before long, however, Jaume would acquire clear proof that his son-in-law was acting not out of concern for the crown of Aragon, but rather to shore up his own political standing.