Cecco Angiolieri (c. 1260 – c. 1312), the son of a banker father and noblewoman mother, lived in Siena and wrote roughly 110 sonnets. He sometimes found himself in legal and financial troubles, and upon his death he left an indebted estate to his children. At some point he met Dante, possibly when both were involved in Siena’s and Florence’s alliance against Arezzo in the Battle of Campaldino (1289). Three of Angiolieri’s sonnets to Dante exist, perhaps as a part of a tenzone or poets’ exchange. (Dante’s responses, if he made them, are unfortunately lost.) As the sonnets featured here attest, he often wrote about love’s cruelties and the hardship of being broke, lamenting in one poem the sturdy health of his father and thus the distant prospects of his inheritance. Dante Gabriel Rossetti first translated some of Angiolieri’s poems into English, and critically he is often identified with a “comic-realistic” school of medieval Italian poetry, which parodied and deflated the courtliness and philosophical high-mindedness of the dolce stil nuovo poets.