Baena, who was a converso (a Jewish convert to Christianity), is best known for compiling and contributing to the Cancionero de Baena, an important medieval anthology composed between 1426 and 1465 containing the poems of over 55 Spanish poets who wrote during the reigns of Enrique II, Juan I, Enrique III, and Juan II.
Montoro was a used-clothes dealer called a ropero who also enjoyed wealthy patrons and used his talent at self-deprecating rhymes that highlighted his unfortunate appearance and Jewish blood.
[8] After this, he appears to have earned a place at the court of Juan II, where he compiled his most well-known work, Cancionero de Baena.
At Juan II's court, he was an escribano de cámara, literally a ‘chamber scribe,’ but more accurately, a ‘royal bureaucrat,' and a part-time jester.
Because of lapses in output and periods of absence in official court records, de Baena “must have been idle or out of grace for long periods during which” he wrote “many abject petitions to the same high patrons and was also at war” with various other poets defending his own talent and attacking others’, most especially that of the much disliked Daviuelo, with whom the famous Alfonso Álvarez de Villasandino also fought metaphorically in poetic debates.
As judino (spelled indino in the original manuscript) is a pejorative term for Jew in Spanish, it is evident that even Baena himself admitted to and identified with his heritage, even in formal matters.
However, according to Alberto Blecua’s and Vicente Beltrán’s research, it appears that some poems were added to the Cancionero by other compilers after his death, making later dates a possibility for the completion if not the genesis of the anthology.
By providing a “theoretical justification in his Prologus, Baena ensures the virtue and prestige of his collection before his patron,” by associating himself and poetry in general with courtly behavior.
[41] Through this theoretical justification, Baena’s makes his own cancionero an important conservation of courtly knowledge while at the same time contributing to contemporary literary theory about the nature and merit of poetry and the poet.
[42] The surviving manuscript, written on paper, was housed at El Escorial from the middle of the 18th century, according to a detailed description by a man named Rodrigo de Castro during the era.
Indeed, much of his research concludes that the ''Cancionero'' that readers are familiar with today was altered by compilers other than Baena, most probably after his death, as the latest poems were composed as late as 1449.
While this advice shares many similarities with Juan de Mena’s Laberinto, in Dezir, Baena also makes his own more unique contributions.
[50] To prove the merit of his advice, Baena uses Alfonso VIII of Castile as an example of what Juan II ought to do and how such a strategy has been successful in the past.
According to Baena, Alfonso’s close leadership brought about stronger national unity and the defeat of many Muslims in Spain at that time.
Baena was not only a gifted compiler, poet, and jester, he also composed political works that showed a greater depth of knowledge and intellect than previously speculated.
Baena’s literary style relied greatly on the use of self-deprecating humor and the ability to mock both himself and others without falling from grace and offending any powerful courtiers.
For Baena, this kind of self-mockery included pointing out “his own ugliness and dwarf-like stature.”[52] In this era, to be a successful fool in court, Baena had to rely on more than “plain ugliness or a crooked spine.”[53] In order to “attain the highest metaphysical level of ‘madness,’” a trait which defined what it was to be a medieval fool and court poet, it was necessary to “open wide the closet and reveal the skeleton within.
And this is what Baena and many others did, seizing every opportunity to make fun of their own Jewish blood and former faith.”[54] Instead of hiding their Jewish roots, as might be expected during this era of intolerance and even persecution of Jews in Spain, in their writing, converso fools were expected to accentuate their ‘mad’ pasts in order to make the court laugh.
Here, Baena’s style worked to diminish the perceived threat of his Jewish Otherness until it was reduced to nothing more than amusing stereotypes about large noses and harmless dietary differences.