The Portrait of a Woman with Gloves is a symbol of judgment. It is the painting that Montgomery steals from Whitewater. He details that it measures eighty-two by sixty-five centimeters. It dates from between 1655 and 1660 and was painted by an anonymous master, sometimes thought to be Rembrandt or Frank Hals. The painting shows a woman of Eastern cast dressed in a black dress with broad white collar and cuffs. She is wearing a brooch. Montgomery feels this woman comes to life and judges him at varying times throughout the robbery.