Amazing Spider-Man Vol.1 #11
Betty's brother has gotten himself into trouble with gambling debts and Betty is forced to help in Doc Ock's plot to break Blackie Gaxton out of prison to keep her sibling alive; Spider-Man interrupts the escape and Blackie shoots Bennett during the conflict; Gaxton is captured but Doc Ock gets away; Peter tries to comfort Betty over the loss of her brother.
Printed: Apr 1964
Writers: Stan Lee
Art: Steve Ditko
Cover: Steve Ditko and Jack Kirby