Khālid al-Kātib, whose lengthy poetic career reached its peak during the caliphate of al-Muʿtaṣim, wrote nearly 600 surviving poems, almost all of them four-line ghazal. He allegedly suffered from madness later in life, spending his last years riding through the streets of Baghdad on a walking stick, pretending it was a horse, while the townspeople heckled him. Despite occasionally acting as a nadīm to several notables, he never earned a living as a court poet and remained employed as a kātib; according to Kitāb al-Aghānī, Khālid did not possess the mindset of a panegyrist. Khālid’s mediocrity is a recurring theme in the biographical anecdotes; the rewards he received from patrons were meager, and he is only ever able to win the favor of young men he admired through the intercession of friends. In fact, the biggest financial reward he ever received for his eloquence was not for a poem; Ibrāhīm b. al-Mahdī gave him enough money to buy a house as a reward for Khālid’s apparently sincere statement that, instead of panegyrics or satires, he writes poems about his own emotions. Kitāb al-Aghānī mentions several invective poems, albeit brief ones, by Khālid against former friends of his. One of the two explanations Kitāb al-Aghānī gives for Khālid’s descent into madness is that he exchanged invective poems with Abū Tammām when the two poets vied for the affections of a youth called ʿAbdallāh. Abū Tammām’s poem referred to Khālid as “cold Khālid,” and thus people taunted him with this nickname until he went mad, and even after. There may be more subtext to the rivalry between Abū Tammām and Khālid al-Kātib than simply a competition for the affections of a handsome youth; the two poets are foils to each other in several ways. Abū Tammām, although he also wrote ghazal, was one of the most celebrated panegyrists of his time, admired by all three Muʿtazilite caliphs, whereas Khālid’s poems suited the tastes of singers, even those of royal blood, like Ibrāhīm b. al-Mahdī. Abū Tammām was an intellectual heavyweight who categorized the motifs of the old Arabic poetic tradition in his Ḥamāsa before repurposing them in his own poems. Khālid was an Arabized Persian kātib the likes of whose knowledge al-Jāḥiẓ considered shallow. Meanwhile, one anecdote shows Abū Tammām acknowledging that one of Khālid’s poetic motifs outshines the old masters.