In an attempt to evade the intensifying manhunt, John had his lawyer Piquett, and his investigator Arthur O'Leary, locate a plastic surgeon to alter his appearance. They arranged for Dr. Wilhelm Loeser and an assistant, Dr. Harold Cassidy, to operate. On May 27, at the home of James Probasco, they went to work on his face. Several days later, they worked on the tips of his fingers, attempting to remove his fingerprints. The end results of the work were highly debatable. Some friends on seeing John later, thought he looked like he had the mumps.
A short time later, the women arrested at Little Bohemia were released and placed on probation. Tommy Carroll, reunited with his wife, drove to Waterloo, Iowa. Acting on a tip, police looked for and then located their car parked in an alley. Later as the Carrolls emerged from a nearby restaurant, the police approached. Carroll went for his gun but one of the officers knocked it from his hand. As he began to run he was shot four times. He would later die in the hospital. The ranks of the Dillinger gang were thinning.
On June 30, still hoping to raise money to leave the country, Dillinger with Van Meter and another man who may have been Pretty Boy Floyd, robbed the Merchant's National Bank in South Bend, Indiana. During the robbery and it's aftermath, there was much gunfire with Van Meter shooting an officer, who later died. Van Meter himself suffered a severe head wound. The resultant take was a mere $4,800 between them.