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Caravaggio led a tumultuous life. He was notorious for brawling, even in a time and place when such behavior was commonplace, and the transcripts of his police records and trial proceedings fill several pages. On 29 May 1606, he killed Ranuccio Tomassoni, a gangster from a wealthy family, in a duel with swords. The circumstances are unclear and the killing may have been unintentional. Caravaggio's patrons had hitherto been able to shield him from any serious consequences of his frequent duels and brawling, but Tomassoni's wealthy family was outraged by his death and demanded justice. Caravaggio's patrons were unable to protect him, and Caravaggio was forced to flee Rome to avoid being arrested for murder.
Many rumors circulated at the time as to the cause of the duel. Caravaggio was in love with [[Fillide Melandroni]], a well known Roman prostitute who had controversially modeled for him in several important paintings, and Tomassoni was her pimp. Some rumors claimed that the duel stemmed from jealousy and that Caravaggio castrated Tomassoni with his sword before killing him after the duel. Several contemporary ''[[avvisi]]'' referred to a quarrel over a gambling debt and a tennis game, and this explanation has become established in the popular imagination.<ref name="Life of Caravaggio">{{cite book|last=Baglione|first=Giovanni|authorlink=Giovanni Baglione|title=Life of Caravaggio|year=1642|location=Italy|url=http://caravaggio.com/preview/attach/data01/D000001.htm|access-date=2013-10-30|archive-url=https://web.archive.org/web/20131101063913/http://caravaggio.com/preview/attach/data01/D000001.htm#|archive-date=2013-11-01|url-status=dead}}
Because of the excessive ardour of his spirit Michelangelo was a little wild and he sometimes looked for the chance to break his neck or to risk the lives of others. People as quarrelsome as he were often to be found in his company: and having in the end confronted Ranuccio Tomassoni a well-mannered young man over some disagreement about a tennis match they challenged one another to a duel. After Ranuccio fell to the ground Michelangelo struck him with the point of his sword and having wounded him in the thigh killed him.</ref>
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