Billie quickly found out what it was like to be the girlfriend of John Dillinger. The perks were being showered with gifts. The down side was being shot at.
On November 15th she went with John to see Dr. Charles Eye, a dermatologist in Chicago, for a ring worm infection he picked up when he was in the Lima jail. This was his second treatment for the condition. Police informer Arthur McGinnis was aware of John's appointments since he is the one who recommended the doctor. Arthur contacted Captain Matt Leach who made preparations for an ambush. Leach had allowed John the luxury of making his first appointment so not to raise suspicions.
They arrived at the doctor’s office at the SE corner of Irving Park Blvd. and Keeler Ave. shortly after 9:00PM that evening. He parked their ’33 Essex Terraplane 8 in front of the building on Keeler. Billie waited in the car while John finished with the doctor. As he and Billie left, he backed around the corner and started forward going East on Irving Park Blvd. The inattentive cops finally figured out that John had left and made chase. John was two blocks away in the right hand lane before they caught up with him. To his surprise they pulled up behind them in the left lane and that is when Art Keller fired five loads of buckshot from a 12 gauge riot gun into the door on the driver’s side of the car. Officer Rooney & Artety fired from behind with revolvers either missed or did nothing.
The faster Essex pulled away from the Ford V-8’s. The officer’s tried to catch up but Johnnie lost them when he turned off their headlights and turned down an alley. The cops drove right by without seeing them. They turned South on Elston Ave. and made their way to Russell Clark’s apartment just in time for a party. John and Billie escaped unscathed but out of breathe from the excitement. Officers found their bullet riddled car abandoned the next day.