The Amazing Spider-Man #336 (1990)
“Return of the Sinister Six, Part Three: The Wagers of Sin”
Writer: David Michelinie
Artist: Erik Larsen
Kingpin hires the Vulture to kill a man named Raymond Trask. Mr. Grouper, an associate of Kingpin’s, hires Chance as backup in case Vulture fails to kill Trask. Peter is photographing an event Trask is hosting when Vulture attacks. Pete changes into Spider-Man and fights him. Chance comes along and tries to kill Trask, but Spidey takes him out and he flies away. Vulture takes Aunt May hostage, but Nathan Lubensky grabs Vulture. Vulture flies up with Nathan hanging on and then drops him. Spider-Man tries to save Nathan, but his heart stops when he’s back on the ground. Dr. Octopus flies by Vulture and gives him a lift.