This photo came about when journalists, talking with John Dillinger and Crown-Point authorities, asked the sheriff (Lillian Holley), the Lake County prosecutor (Robert Estill) and John Dillinger (the captured gangster) to pose.
Holley was serving-out the term of her husband (who had been sheriff when he was killed in a shoot-out). The FBI tells us the following about the impact of this picture on Holley and Estill:
On that day [when this picture was taken], Dillinger was 30 years old. He was of medium build and average height, with brown, thinning hair. His most distinguishing feature was a roguish smile, which he had put to good use in a series of press photos with the prosecuting attorney Robert Estill and the sheriff upon his extradition to Crown Point. The chummy nature of the photos contributed to both these officials losing their jobs that year.
Click on the image for a better view.
Photo online, courtesy FBI.