Caravaggio was a complicated man, working in a complicated day, in a complicated city. As he ushered in the Baroque movement, playing with contrast, bending light with darkness, the Church was preoccupied with the game of highlighting or suppressing voices to maximize their power and minimize dissent. A well-known product of this is the struggle Galileo had in confirming that the earth revolved around the sun and not the other way around. Giordano Bruno was publicly burned at the stake for similar reasons. Often excluded from historical narratives of this time is the public execution of Beatrice Cenci and her family for reasons that leaned more towards political power and less towards moral judgement. Many Caravaggio historians point to Cenci’s death as the inspiration behind the common motif of beheadings in his paintings. Able to navigate between both the high and low cultures of Rome, Caravaggio provides a window into the way these societies interacted, one of many things that drew me to him and his story. He was also a person in his own right, with thoughts and feelings that we may never have the complete picture of, though he’s left us clues in his works and actions. Far less has been preserved of Prospero, Anna, Fillide, and Mario. This is my attempt to fill in the blanks.