A distant relative of Meir HaLevi Abulafia, but no relation to Avraham, Todros Ben Yehuda Abulafia was born in Toledo in 1247 and spent most of his life in that city, where Arabic was still in use some one hundred and fifty years after it had been retaken by Christians. Todros studied Arabic early on and commanded both the language and its literature; he was probably also familiar with Christian vernacular literature. An ambitious poet who was anxious to make his way in the culturally rich court of King Alfonso X (the Wise), of Castile (r. 1252–84), Todros managed to attach himself to a wealthy and influential Jewish courtier, dedicating numerous poems to him and being rewarded in turn with—among other things—clothes, funds, chickens, goats, and a donkey. He was even granted an audience with the king himself (see “Before the King,” below). Apart from his work as a poet in the context of the Jewish courts, Todros served as a senior tax collector and diplomatic envoy. His luck turned in 1279, when the increasingly religious king ordered Todros’s patron to raise an extravagant amount of money from the Jewish community in order to support a military campaign. The king’s son, however, diverted the funds for his own purposes, and the troops were stranded; Alfonso’s anger led to the execution of the patron (along with another leading tax collector). Two years later most of Castile’s Jews—Todros among them—were rounded up while at synagogue and put in prison, where they were held for ransom. Todros wrote numerous poems during this period of imprisonment and was released later that year. Somewhat subdued by his time in jail and his fall from grace, he managed to regain a measure of prominence in the court of Alfonso’s son and successor, Sancho IV (d. 1295), and his ambition once again took hold. Though contemporary documents complain of the slack standards of religious observance at the time and a general trend toward assimilation among the upper classes, Todros maintained his faith, and this despite his wild ways and clear predilection for Christian and Arab women—a preference that finds powerful and colorful expression in his poetry.

We have scant information about Todros’s later life, and firm evidence of him vanishes after 1298, when he collected his poems into a diwan, which he called Gan HaMeshalim veHaHidot (The Garden of Parables and Riddles). He gave the poems descriptive headings in traditional fashion (though for the most part in Hebrew rather than Arabic) and introduced the entire collection with an apology that echoes similar statements in HaNagid’s diwan and Ibn Ezra’s criticism. After the poet’s death, his poetry is rarely mentioned in the literature for another six hundred and twenty-five years. We now know that the diwan was copied in the seventeenth century, in Egypt, and that the manuscript then passed from hand to hand among antiquarian collectors in Iraq and India. At some point Sha’ul ‘Abdullah Yosef, an Iraqi businessman and an amateur but extremely learned scholar of Hebrew poetry, got hold of that seventeenth-century manuscript while he was working in Hong Kong(!), and made a hand-written copy of Todros’s treasure trove for his own research. Yosef’ died of blood poisoning in 1906, and the manuscript came into the possession of one of the leading scholars of medieval Hebrew poetry at the time, David Yellin. Yellin prepared a critical edition which was published in three volumes from 1934 to 1937. With that publication, some twelve hundred poems were added to the medieval Hebrew canon.

Critical evaluation of the poems in Gan HaMeshalim has varied widely. Todros has been looked upon as everything from “one of the greatest poets of whom the Jews can boast,” to an egocentric graphomaniac who lacked national consciousness and was of interest primarily to historians, to “a mediocre epigone” whose work is “repetitive and superficial.” Taken on its own terms, his large oeuvre reveals Todros to be among the liveliest of the Silver Age Spanish-Hebrew poets. He constantly widened the boundaries of the art and, in addition to his many accomplished poems in the familiar Andalusian modes, composed concrete or pattern poetry and some verse that was likely influenced by the troubadour tradition. Two of his poems treat the concept of “spiritual love.” Above all, Todros’s work is distinguished by its freshness and candor: he managed to introduce a vivid (though not always straight forward) personal dimension into his verse that went well beyond anything medieval Hebrew poetry had seen before him. He filled the classical conventions with irony, turned them on their heads, or did away with them altogether and created new poetic space in which to work. His one hundred and thirty–plus Todrosi’ot, as scholars have come to call them, establish what is virtually a new hybrid genre. Short poems constructed along a five-letter acrostic of the poet’s first name, they ground the poet’s intimate conversation with his God in the most profane circumstances. Perhaps the most unusual of all the “sacred” poems in the Hebrew canon, they lack any liturgical function whatsoever. In short, Todros Abulafia is easily one of the most surprising poets of the entire period, though his work is not often read by non-specialist Hebrew readers and is almost completely unknown to readers of poetry in English.