Family lore says their shotgun played a role in the Chicago St. Valentine’s Day Massacre. Why is this miniature of Washington more than a piece of art? A portrait sketched in a WWII prison leads to a meeting 65 years later.

Two generations of prominent Chicago families say this 12-gauge shotgun played a role in the St. Valentine’s Day Massacre. Can HISTORY DETECTIVES confirm their story? Then, combing through documents in one of Manhattan’s first taverns, a man finds a miniature painting of George Washington’s profile. Why is this find much more than a piece of art? And, 65-years ago a fellow prisoner sketched George Silva’s portrait from inside a World War II German prisoner camp. George wants to find out what happened to the artist. His search leads to a moving meeting. These three encore segments first aired as part of three different episodes in HISTORY DETECTIVES' seventh season in 2009.