Got ‘im!
Amazing Spider-Man (Vol. 1) #277
Published: c. March, 1986?
Cover Date: June, 1986
“The Rules of the Game!”
Writer: Tom DeFalco
Artist: Ron Frenz
Inker: Bob Layton
Letterer: Rick Parker
Colorist: Bob Sharen
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And both became mayor.
Coincidence? I think not.
Kingpin: “He webbed me to my chair!”
Jameson: “Yeah, he does that to me too.”