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.