The Jewish community of Toledo, the Castilian capital—the "Crown of Israel" of the Middle Ages, and, in a measure, the Jerusalem of the Occident—did not number, after the raising of the siege, as many hundreds of Jews as previously thousands. The remainder of the Jews of Castile had been reduced to beggary by the depredations and confiscations of friend and foe. Not a few, in their despair, had thrown themselves into the arms of Christianity. A striking picture of the unhappy condition of the Castilian communities at this period is furnished by a contemporary writer, Samuel Çarça: "In truth, plunderers followed on plunderers, money vanished from the purse, souls from the bodies; all the precursory sufferings of the Messianic period arrived—but the Redeemer came not!"
After Don Henry's victory, the Jews had good reason to tremble. One pretext for making war on his brother was the favor shown by Don Pedro to Jews. Now he had become the arbiter of their destinies. Would he not, like another Vespasian or Hadrian, place his foot on the necks of the vanquished? The gloomiest of their anticipations, however, were not realized. Don Henry II was as little able to dispense with the Jews as his predecessors, or the French and German princes. Jews were the only financiers able to keep the state exchequer in prosperity and order, and for this purpose Don Henry stood in need of them more than ever. During the war he had incurred debts for the payment of the troops with which Du Guesclin had assisted him, and for help received in other quarters he had made promises which had to be redeemed. The country had become impoverished by the protracted war. Who was to procure the necessary sums, and provide for the systematic collection of the taxes, if not the Jews? Henry was not blind to the merits of the Jews exemplified in their constancy to his brother. Instead of punishing the conquered, he appreciated their fidelity, saying: "Such subjects a king must love and reward, because they maintained proper loyalty to their conquered king unto death, and did not surrender to the victor."
Don Henry, then, was guilty of the conduct which, in the case of his brother, he branded as a crime in the eyes of all Christendom; he employed able Jews in the service of the state, confiding to them the finances in particular. Two Jews from Seville, Don Joseph Pichon and Don Samuel Abrabanel, he appointed to important posts, the former as receiver general of taxes, and Almoxarif to the king, by whom he was held in high esteem. Other Jews, distinguished for their ability or their wealth, had access to Don Henry's court.
If the king bore the Jews no grudge for the part they had taken in the war against him, the general population was not so magnanimous. The nobility and the commonalty could not forgive their having confronted them as foes in the besieged towns and on the open battle-fields. A passion for vengeance, linked with the usual Jew-hatred, blinded them to the benefits which the Jews contributed to the welfare of the state, and their only thought was how to gratify their resentment. The Jews, being the vanquished, ought, as they thought, to be reduced to a kind of serfdom. The hostile feeling of the populace manifested itself on the assembling of the first cortes at Toro (1371). Here the enemies of the Jews opened the attack. The cortes expressed to the king their displeasure that this "evil, audacious race," these enemies of God and Christendom, were employed in "high offices" at court and by the grandees of the realm, and that the farming of the taxes was confided to them, by which means feeble Christians were held in subjection and fear. The cortes accordingly made explicit demands upon the crown with respect to the Jews. From that time forward they were not to be eligible for any kind of state employment; they were to live in Jewish quarters separated from the Christian population, be forced to wear Jew-badges, be prohibited from appearing in public in rich apparel, from riding on mules, and from bearing Christian names. To Don Henry these demands were very unwelcome, but he dared not refuse some concessions. The majority he dismissed with the remark that in his treatment of Jews he only followed the example of his ancestors, especially that of his father, Alfonso XI. The two restrictions conceded were, if not of material significance, yet calculated to have a sinister effect. These were that the Castilian Jews should don the degrading badges, and give up their Spanish names. The pride of the Jews, equal to that of the grandees and the hidalgos, was deeply wounded. A century and a half had elapsed since the canonical law concerning the Jew-badge, the outcome of papal intolerance and arrogance, had been promulgated. During the whole of that period the Jews of Castile had been able to prevent its application to themselves, but now they also were to be compelled to wear the stigma on their garments. They who had been accustomed to hold their heads high, and rejoice in sounding titles, were, like the German Jews, to slink along with downcast eyes, and be called by their Oriental names. They could not accustom themselves to this humiliating situation.
In consequence of an outcry made by some of his subjects, who had been ruined by loans from Jewish creditors, and complained of usurious interest, Don Henry made encroachments upon their private rights. He decided that if the Christian debtors discharged their obligations within a short space of time, they need refund only two-thirds of the principal borrowed.
The misery resulting from the civil war and the new restrictions exercised a depressing effect on the Castilian Jews. Their most prominent men, those who had access to court, and possessed wealth and influence, especially Samuel Abrabanel, exerted themselves to remedy the gloomy state of affairs. They particularly endeavored to restore the abased, impoverished, and disorganized community of Toledo; but it was beyond their power to revive the scholarly culture and intellectual distinction to which the Toledo community had been as much indebted for its leading position as to the prosperity of its members. The unhappy war, and the evils following in its trail, had stunted the Jewish mind, and diverted it from intellectual to material interests. Disorganization proceeded with great strides. Indifference to scientific work resulted in so general an ignorance, that what formerly every tyro was familiar with now passed for transcendent wisdom. We have an example of the mawkishness to which the new Hebrew poetry had fallen in the verses of the poetaster Zarak (Zerach) Barfat, who, in a poetical paraphrase of the book of Job, completely marred the beauties of that work of art. Just at this period men of learning and ability were urgently required, for representatives of Christianity began to make earnest and energetic attacks on Judaism to obtain converts from amongst its adherents.
Don Henry had much to thank the clergy for; they had sanctified his usurpation, and acquiesced in his arrogated succession. From gratitude and a false conception of religiousness, he conceded much to them. At his command, Jews were again forced to take part in religious debates, in which there was much to lose and nothing to gain.
Two baptized Jews received from the king the privilege of holding religious discussions in every province and town of Castile, which they might compel Jews to attend.
One of these apostates was John of Valladolid. At Burgos the discussion took place before Archbishop Gomez of Toledo. At Avila the whole community was compelled to repair to the great church (1375), where the debate was carried on in the presence of many Christians and Mahometans. Moses Cohen de Tordesillas, who was as familiar with Christian as with Jewish theological authorities, appeared on behalf of the Jews. He entered upon his dangerous enterprise with trepidation, for he had had an opportunity to form an estimate of Christian charity. During the civil war, Christian marauders had robbed him of all his possessions, and had even personally ill-used him in order to force him to embrace Christianity. All these trials he had suffered with the courage of strong convictions, but he had become so poverty-stricken that he had to accept support from the community of Avila.
Moses de Tordesillas did not find his part in the discussion too difficult. The apostate John of Valladolid laid stress on the proposition that the dogmas of Christianity—the Messianic claim, the Divinity and Incarnation of Jesus, the Trinity, and the Virginity of the "Mother of God"—could be demonstrated from the Old Testament. It was consequently not difficult for his Jewish opponent to confute his arguments. After four debates John was obliged to abandon his task, vanquished. This, however, did not conclude the matter. A pupil of the apostate, Abner-Alfonso, appeared soon after, and challenged Moses de Tordesillas to a debate on the Talmud and Agadic texts. In case of refusal, he threatened publicly to impeach the Talmud as the source of anti-Christian sentiments. Moses was again forced to meet a series of silly assertions and charges, and to drag himself through the thorny length of another controversy. By the advice of the Avila community, he committed to writing the principal arguments used in these discussions under the title, "Ezer ha-Emuna," and sent them to his Toledan brethren for use under similar circumstances. Moses de Tordesillas' disputations, notwithstanding the difficulties of his position, were characterized by calmness and equanimity. Not a word of abuse or invective escaped him, and he counseled his Toledo brethren not to permit themselves to be tempted by their zeal to vexatious expressions, "for it is a fact," he said, "that the Christians possess the power and disposition to silence truth by force." Toledo, formerly recognized as the teacher of Jewry, was now obliged to play the part of pupil, and follow formularies in the disputations to which its members might be invited.