John William Cheever was the second child of Frederick Lincoln Cheever and Mary Liley Cheever. His father was a prosperous shoe salesman and Cheever spent much of his childhood in a large Victorian house, at 123 Winthrop Avenue, in the then-genteel suburb of Wollaston, Massachusetts. In the mid-1920s, however, as the New England shoe and textile industries began their long decline, Frederick Cheever lost most of his money and began to drink heavily. To pay the bills, Mary Cheever opened a gift shop in downtown Quincy—an "abysmal humiliation" for the family, as John saw it. In 1926, Cheever began attending Thayer Academy, a private day school, but he found the atmosphere stifling and performed poorly, finally transferring to Quincy High in 1928. A year later he won a short story contest sponsored by the Boston Herald and was invited back to Thayer as a "special student" on academic probation. His grades continued to be poor, however, and, in March 1930, he was either expelled for smoking or (more likely) departed of his own accord when the headmaster delivered an ultimatum to the effect that he must either apply himself or leave. The eighteen-year-old Cheever wrote a sardonic account of this experience, "Expelled," which was subsequently published in The New Republic.
Around this time, Cheever's older brother Fred, forced to withdraw from Dartmouth in 1926 because of the family's financial crisis, re-entered his life "when the situation was most painful and critical," as John later wrote. After the 1932 crash of Kreuger & Toll, in which Frederick Cheever had invested what was left of his money, the Cheever house on Winthrop Avenue was lost to foreclosure. The parents separated, while John and Fred took an apartment together on Beacon Hill, in Boston. In 1933, John wrote to Elizabeth Ames, the director of the Yaddo artist's colony in Saratoga Springs, New York: "The idea of leaving the city," he said, "has never been so distant or desirable." Ames denied his first application, but offered him a place the following year, whereupon Cheever decided to sever his "ungainly attachment" to his brother. Cheever spent the summer of 1934 at Yaddo, which would serve as a second home for much of his life.