Roger was the youngest son of Tancred of Hauteville by his second wife Fredisenda. He arrived in Southern Italy soon after 1055. Geoffrey Malaterra, who compares Robert Guiscard and his brother to "Joseph and Benjamin of old," says of Roger: "He was a youth of the greatest beauty, of lofty stature, of graceful shape, most eloquent in speech and cool in counsel. He was far-seeing in arranging all his actions, pleasant and merry all with men; strong and brave, and furious in battle." Roger shared the conquest of Calabria with Robert, and in a treaty of 1062 the brothers in dividing the conquest apparently made a kind of "condominium" by which either was to have half of every castle and town in Calabria.
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