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This article addresses the overlapping backstories to the first three of four auto fatalities that affected F. Scott Fitzgerald’s life and art. It explores biographical information about Fitzgerald’s relationship with his rich St. Paul neighbor Stuart Beebe Shotwell Jr., and two Princeton classmates, Robert E. Sniffin and Charles O. Wiegand. All three individuals died in automobile accidents that deeply cut into Fitzgerald’s psyche. At age thirteen young Fitzgerald saw Mr. Shotwell get run over by a pretty woman driving a fancy car. Seven years later, on the eve of World War I, two of his former Princeton dorm-mates were killed in DUI accidents one night apart. These terrible events may have caused deep-seated trauma for Fitzgerald. This article argues that the author infused an array of “focal points” and Wordsworthian “spots of time” emanating from those traumatic events into This Side of Paradise and prepared Fitzgerald to dramatize a fourth automobile fatality in The Great Gatsby.