The Amazing Spider-Man #286 (1987)
“Gang War, Part Three: Thy Father’s Son!”
Writer: Jim Owsley
Artist: Alan Kupperberg
Richard Fisk (Kingpin’s son) meets a girl in the park and reveals to her that he has infiltrated the criminal world as Rose to try and take it down from the inside. And he’s never technically committed any crimes. Also, the doctors taking care of his ill mother are purposefully keeping her ill. There’s another big meeting between Rose and The Arranger, where they will try to come to some alliance agreement. New York’s police force surrounds the area, waiting to strike. One of the cops is spotted and it begins a huge firefight and also a fire that spreads a few blocks. As the madness ensues, Spider-Man rescues people from the fire, and a gunshot wounded Rose accidentally kills a rookie cop. It is the first innocent person he’s ever killed.