Benedict IX
Theophylactus of Tusculum · 1032 – 1048
The only man to serve as pope three separate times, and the only one who reportedly sold the office.
Benedict IX first became pope around 1032, when he was probably still a teenager, installed by his powerful Tusculan family. His conduct was scandalous enough that the Romans expelled him in 1044 and elected a replacement. Benedict returned, then decided to resign so he could marry, selling the papacy to his godfather, who became Gregory VI. Benedict changed his mind and tried to reclaim the office, creating a situation where three men all claimed to be pope. Emperor Henry III sorted it out at the Synod of Sutri in 1046 by deposing all three and installing a German bishop. Benedict tried to seize Rome one more time in 1047. He eventually retreated to the Abbey of Grottaferrata, where some sources say he repented. He is the only pope to have reigned three distinct times.
Three Times a Pope
Benedict IX's career reads like a dark comedy. Installed as a teenager, expelled, returned, sold the office, regretted selling it, tried to take it back, was deposed by an emperor, and tried yet again. His pontificate represents the nadir of the papacy before the Gregorian reform movement cleaned things up.
Did He Really Sell It?
The traditional account says Benedict sold the papacy to Gregory VI for a sum of money. Gregory VI's supporters claimed it was more of a negotiated resignation. Either way, the whole episode convinced serious churchmen that the papacy needed structural reform, which came under Leo IX and Gregory VII.