Eventually, Mad Howard feigns suicide and leaves behind his city life. Over the years, Mad Howard's love for Old Matt's daughter and his guilt over abandoning her slowly drove him insane. Meanwhile, Old Matt has sworn he will kill the man who abandoned his daughter, as well as his father, if ever he finds them. However, he never told his father about Old Matt's daughter and his relations with her the secrecy drove a wedge between Mad Howard and his father, although his father never understood why. Once returning to the city, Mad Howard sent her a letter explaining that his father would not approve of their marriage. Mad Howard packed up his paintings and returned to the city, leaving Old Matt's daughter with the impression that he would return. However, Mad Howard believed that his father's pride of family and place in society would never allow him to approve of his son's marriage to an Ozark country girl. That painting was of a young girl, pretty, standing beside a creek the girl in the painting was Old Matt's daughter, with whom he had fallen in love. Years earlier, Mad Howard returned home after spending time painting in the mountains, and one of his paintings became famous, as did he. Old Matt and the Shepherd's common history (which only The Shepherd knows at the outset) involves Old Matt's daughter, who died while giving birth to her son (and Old Matt's grandson), Pete Howard: unbeknownst to the Matthews, Mad Howard is Pete's father, and thus The Shepherd is Pete's grandfather. Howitt's reclusiveness has earned him the moniker "The Shepherd of The Hills", yet he befriends the Matthews clan (the strongest and most respected family in the area) who come to love and trust him. Howitt spends his time alone, acting as a mediator and friend to the mountain people, and trying to recover from his tragic past, which includes the prior deaths of his wife and children, and the later presumed madness and subsequent suicide of his only surviving child, his artist son (later referred to as "Mad Howard"). The main story surrounds the relationship between Grant "Old Matt" Matthews Senior and Dad Howitt, an elderly, mysterious, learned man who has escaped the buzzing restlessness of the city to live in the backwoods neighborhood of Mutton Hollow. The story depicts the lives of mountain people living in the Ozarks. The people he encountered during his eight summers spent camping on the Rosses' land were the inspirations for his characters in the book. In following his doctor's advice, he became acquainted with John and Anna Ross, known locally as Old Matt and Aunt Mollie. Wright began visiting the Ozark Mountains in southern Missouri and northern Arkansas in 1898 at the bidding of his physician, who recommended two vacations a year in a more suitable climate for health reasons.
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