The Amazing Spider-Man #11 (1964)

In Amazing Spider-Man Issue #11, our web-slinger hero is faced with the return of Doctor Octopus, his longtime nemesis. Peter Parker is lost in thought when he learns of Doc Ock's release from prison on the radio news. Spidey sets out to stop his archenemy, but the prison warden refuses to listen to him. Meanwhile, Doctor Octopus is strategizing in his cell. Peter works on a tracking device named the Spider-Tracer and throws it on the car Doc Ock and Betty Brant are driving away in. The pursuing Spider-Man eavesdrops on their conversation and finds out that Betty's brother is involved with Blackie Gaxton, a criminal. In Philadelphia, Spider-Man tries to stop Blackie and Doc Ock from breaking out of jail. However, the police mistake him for a criminal and begin to chase him. In the chaos, Bennet Brant, Betty's brother, is shot by Blackie and dies. Betty blames Spider-Man for her brother's death and attacks him. Spider-Man fights Doc Ock but loses him in the end. Betty later confides in Peter about her brother's involvement with Blackie.