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Years in power
Had his predecessor exhumed, tried, de-fingered, and thrown to the river
Ordered the murder of another pope and the only known to have fathered an illegitimate son who later became pope
Aged only 18 when elected pope, he raped female pilgrims, consecrated a 10-year-old boy as bishop, invoked pagan gods, gave land to a mistress, and was killed by a man who caught him in bed with his wife.
Split the church's finances among his relatives
Gave up his papacy twice in exchange for a large sum of money
1032-1044 and 1047-48
Approved the use of torture to extract confessions of heresy
Complained he not hear enough screaming when Cardinals who had conspired against him were tortured
Took Italy by force, fathered at least seven, and possibly as many as ten illegitimate children, and threw large parties, bordering on orgies
Also a Medici, whose power-politicking with France, Spain, and Germany got Rome sacked.
Sold indulgences to reconstruct St. Peter's Basilica and had cardinals assassinated