(antipope Feb. 997–May 998: d. 26 Aug. 1001)
A Greek from Rossano in Calabria, John Philagathos was appointed chancellor for Italy (980) and then (982) abbot of Nonantola, near Modena, by Emperor Otto II (973–83). After Otto's death his widow Empress Theophano made him (987) tutor to her 7-year-old son, King Otto III (emperor 996–1002), and then bishop of Piacenza (988), Pope John XV raising this see for his sake to an archbishopric and detaching it from Ravenna. In 991 he again became chancellor for Italy, and in 994 was sent as special envoy to Constantinople to find a Byzantine princess as bride for Otto III. He returned to Italy, accompanied by a Byzantine ambassador, Bishop Leo of Synada, in early Nov. 996, shortly after the Roman rising against Gregory V and his expulsion by Crescentius II Nomentanus, now dictator of Rome. While Leo went to Rome, John Philagathos spent some weeks in north Italy, where he was in touch with Emperor Otto III at Aachen as well as with Crescentius. In early Feb. 997, when Gregory, still exiled from Rome, held a synod at Pavia, there were rumours that a fresh papal election was pending, and shortly after John Philagathos, visiting Rome ostensibly as a pilgrim, allowed himself to be elected and installed as John XVI.
What prompted his decision, apart from vain ambition, was powerful pressure from Crescentius and the Greek envoy Leo; the former hoped that the emperor, alienated from Gregory V and aware of his unpopularity, would be content to see such a trusted friend on the papal throne, while the latter (as he boasted in letters home) could see only advantage for Constantinople in separating Rome from its German master. But the usurper was not allowed to enjoy his new role for long. In Mar., by order of emperor and pope, he was replaced as abbot of Nonantola and archbishop of Piacenza; either then or soon after his formal excommunication followed. In summer 997 he received a highly critical letter from his saintly compatriot, Abbot Nilus of Rossano (c. 910–1004), who sharply rebuked him for his unchristian ambition, and also severe remonstrances from his former pupil Otto, for the moment detained in Germany. It must by now have become clear to him that he was no more than Crescentius' creature, confined to purely spiritual functions. By early autumn he was promising to submit to all the emperor's demands, but Crescentius prevented any negotiation by putting the imperial messengers under lock and key.
In Dec. 997 Otto marched with his army into Italy; John abandoned his cause as lost and fled to the Campagna—a fact which explains the attribution to him, in most papal lists, of a reign of ten months. In Feb. 998 Otto, accompanied by Gregory, entered Rome, which opened its gates without resistance. A detachment of troops led by Count Berthold discovered the usurper in a fortified castle, seized him, and handed him over to a Roman monastery. Either at his capture or, more probably, later with the consent of emperor and pope, he was blinded and appallingly mutilated in his nose, tongue, lips, and hands; he was then paraded around the city, sitting back to front on an ass. Later, probably in May, a formal trial was held under the presidency of Gregory, and he was condemned, deposed, degraded from his priestly rank, and ritually stripped of his pontifical robes. Abbot Nilus, who had interceded in vain for him, was furious and left the city on the same day, placing a curse on both Otto and Gregory. Finally, the broken and humiliated man was shut up in a Roman monastery, where he was allowed to receive occasional visits and where he lingered on until 26 Aug. 1001.