While he had elite patrons, he spent much time with unsavory people.

He was often in trouble with the law and even accidentally killed a man in 1606 before becoming exiled. His painting Portrait of a Courtesan (1597) is a look into the rather dark side of Caravaggio's life.

The woman in Portrait of a Courtesan by Caravaggio is commonly believed to be a famous prostitute, or courtesan, named Fillide Melandroni. She appeared in a few other paintings by Caravaggio during the 1590s - Saint Catherine, Martha and Mary Magdelene and Judith Beheading Holofernes - and may have been in more.

The exact number is unknown as a number of Caravaggio's paintings have been lost or destroyed. Fillide was considered to be one of Rome's most famous prostitutes of this era and found success in the streets of the city as well as with the upper class. Caravaggio and Fillide are supposed to have shared a close relationship.

The identification of the flower being held by the courtesan has differed depending on the art historian. Originally, it was believed the flower was an orange blossom or bergamot which is symbolic of marriage and fidelity. This led some to believe the woman was actually the wife of a friend of Caravaggio. However, others identify the flower as jasmine, which is symbolic of erotic love.

This flower identification better coincides with the title of the painting, Portrait of a Courtesan. Furthermore, a list of paintings belonging to Caravaggio's patron, Marchese Vincenzo Giustiniani, from 1638 shows a piece described as a portrait of a courtesan named Fillide. This is easily the most obvious identification of the painting's subject and should put any debate to rest.

Unfortunately, the original copy of Portrait of a Courtesan was destroyed in 1945 in Berlin. Only copies and photographs remain of this painting that revealed one of the sides of Caravaggio's tumultuous and rather short life.