It appears that somehow Gonçalo Vasques de Azevedo heard about what had happened to Nuno Álvares in Coimbra and how he was short of money. He wrote immediately to the King of Castile, saying that he thought it would be a good idea to offer him some money to ascertain how he would respond, and if he would change sides because of the dire financial position in which he found himself. Furthermore, if the king had him on his side, then not only would a great burden be removed from his concerns, but he would also be sure to achieve everything he had hoped for.

The King of Castile's response to this was that it did not seem right and proper to him that such a thing should be proposed to Nuno Álvares in his name, because, if it happened that he did not accept his offer, he might go around boasting and saying that the king had tried to plead with him and entice him with a bribe, for which everyone would hold the king himself in low esteem. Instead, Gonçalo Vasques should arrange for the offer to be made to Nuno Álvares in a different way, as though on his own initiative. If Nuno Álvares were persuaded to accept something and gave any sign that, if he received as much as he wanted, he would go over to the king's side, then Gonçalo Vasques should promise him whatever he wanted and should let the king know everything that had happened right away.

Then Gonçalo Vasques spoke to a Jew by the name of David Alguaduxe, the brother of the wife of Dom Yehuda, who had been treasurer to King Fernando. The Jew went to see Nuno Álvares in Tomar where he was staying and told him that he had heard that he was badly in need of money, and that he, Dom David Alguaduxe, had in his possession certain monies belonging to the King of Castile and, if he was willing to accept some of that, then he would let him have 1,000 dobras to begin with, and the time would come, some day in the future, when he could pay the king in service.