Marvel Comics © April 1964, The Amazing Spider-Man #11.  The story "The Long-Awaited Return of Doctor Octopus!".  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.

Characters:  Bennett Brant (death); Betty Brant; Doctor Octopus [Otto Octavius]; Aunt May Parker; Spider-Man [Peter Parker]; Blackie Gaxton

Script: Stan Lee   Pencils: Steve Ditko, Jack Kirby   Inks: Steve Ditko, Jack Kirby 

This book appears (g/vg 30), w/ the expected nics, tics, wear and tear.  Thanks for looking.     711c-2309-30