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Though numerous characters have been portrayed in this volume of short stories, there are some characters who are common to almost all the stories. Since the entire book is a detailed description of the people of a small town like Winesburg, it is expected that certain characters would get repeated in more than one story.
The best reference to this is of George Willard. George is the son of Tom and Elizabeth Willard and he is brought up in this little town. Certain chapters depict him in a central role, with a detailed description of his childhood, his love and even his final departure from his hometown. Yet, in many stories he is merely a character through whom the other main characters reveal their deepest of emotions and feelings. For example, Wing Biddlebaum befriends only George in the entire town. Wash Williams reveals the sordid details of his married life to George. Enoch Robinson too reveals his sorrows to George Willard. Thus George's presence in each of the stories acts as a catalyst to purge the emotions of the other characters.
George's growth from a young lad uncertain of his future, to becoming a young reporter at the 'Winesburg Eagle', to finally his decision to leave Winesburg and search for better prospects has been carefully charted out. Most of the stories reveal him as the young reporter flitting from place to place in search of a new item to print in the newspaper.
George's relation with Helen White has also been graphed out, in many of the stories. A reference to childhood mates is made and their bonding towards each other later too is shown. George cannot bear any other man commenting on having any feelings for Helen. In 'Drink', when Tom Foster calls out her name in his drunken stupor, George gets annoyed. Similarly to Seth Richmond in 'The Thinker', George mentions his love for Helen White.
Yet at the end in the final story 'Departure', George leaves Winesburg without a backward glance at Helen, who had come to see him off. At this stage, probably a career is far more important that a girlfriend.
What makes this volume of short stories a class apart from other short stories, is the ingenious linking of one story to another with threads composing of characters, place, and certain similarities of mannerism.
The author Sherwood Anderson strives to make use of certain physical characteristics, which are common in many of the stories. The finest example is the symbolic use of the hands. Hands play a major part as a linking factor among many of his stories. The first story is titled 'Hands' and dwells on a character who has a habit of using his hands while talking. When he unconsciously uses it to caress his students it is given sexual connotations and he is ostracized from the community.
In the next story 'Paper' pillsí a reference to hands is made. 'The knuckles of the doctors hands were extraordinary large. When the hands were closed they looked like clusters of unpainted wooden balls." In 'The philosopher', the saloon keeper has 'peculiarly marked hands.'
In 'Respectability', Wash Williams who is otherwise a grotesque, unclean man, his hands are surprisingly clean. 'His fingers were fat but there was something sensitive and shapely in the hand.'
This is an example of Sherwood Anderson's exquisite style of writing which attempts at threading together some of the stories with at least one unifying element.