The Education of Sidney Adams: Anderson’s “Letters to Cynthia”

By Charles E. Modlin

Of the many unfinished manuscripts that Sherwood Anderson left behind, one of the most interesting is “Letters to Cynthia,” a rare experiment in epistolary fiction, which follows the adventures of a brother and sister as they venture outside their small Midwestern hometown and explore the bohemian intellectual worlds of New York and Chicago. It provides some detailed observations of the Chicago literary scene in the period following the publication of Winesburg, Ohio (1919) and explores a major theme in Anderson’s published works: the Midwesterner distracted away from his family and business toward the world of the arts. On a personal level, it also expresses a characteristic ambivalence toward the relative merits of country vs. city life, which Anderson retained throughout his life.

The fourteen-page manuscript,1 which is housed at the Newberry Library in Chicago, begins with a section in Anderson’s handwriting that introduces Sidney and Cynthia Adams. He is a pump manufacturer living in La Salle, Illinois, an actual town, 85 miles southwest of Chicago; she is his sister, who has gone off to live in Greenwich Village, New York. The narrator, purportedly Anderson himself, explains that he had met Sidney through writing advertising for the pump company. This part also includes a brief, incomplete letter from Sidney to Cynthia, which provides some background on their father and their recently deceased mother. The mother, “the stronger and sweeter” of the two, left her money to the children, and the father, who was originally from New England, has become moody and resentful.

The rest of the manuscript, which is typed, apparently by Anderson, consists of four detailed letters–three from Sidney to Cynthia and one from her to him. Sidney writes the first of these from the Auditorium Hotel in Chicago, staying over after seeing her off on the train to New York. He reports that he had visited Krock’s bookstore on Michigan Avenue and bought a copy of The Education of Henry Adams.2 Feeling culturally deprived, he asks Cynthia to write him the literary news from New York. “Sometimes,” he observes, “I think you and I have lived as isolated lives out there at La Salle as La Salle himself could have lived when he and his Indian guides first came into the country and set up housekeeping on Starved Rock.” He laments his own isolation at home now that Cynthia has gone. While he is happy with his wife, Hallie, she doesn’t fully share his interest in books, art, and music. He misses his long walks in the country with Cynthia and describes one particularly happy afternoon when she induced him to leave the office to go hiking in the Midwestern countryside. He recalls that “you kept laughing about nothing and so did I. It was an odd sort of afternoon for two Adamses to put in.”

The next letter, written by Cynthia after her arrival in New York, expresses her misgivings about leaving home. She wonders whether she has exaggerated the defects of life in La Salle and has already experienced petty irritations with the trendy airs of Greenwich Village as expressed by the friend with whom she is staying:

Fanny has grown to be what she calls “esthetic” since you thought her so charming years ago at college. Of course her hair is short but she’s careful to explain that her first haircut was contemporary with Mrs. Vernon Castle’s, when cutting one’s hair was something of a revolt; and that as to clothes, they take too much time from “the real things of life.” I suggested mildly that clothes were about as solid realities as I could grasp and that since you had to wear some sort, in any case, good ones took no more trouble than bad ones if one had any eye for such things. But she just sniffed at that. The truth is that she spends more than she should on rent and always feels too poor for clothes. That’s nothing to her detriment, but why pretend? I gathered that my idea was Middle Western, than which there is nothing lower in the eyes of the Village.

Despite her criticisms, Cynthia concludes that “Fanny and her friends are really kind and jolly and have some freedom and opportunities of companionship that we have always hungered for.”

Sidney answers Cynthia’s letter, again lamenting that she is unavailable, and Hallie too busy, to roam the countryside with him after work, which he has prized as a time to escape the small-town preoccupation with “the details of existence.” He expresses reservations about Fanny and hopes that Cynthia won’t bob her hair, since “An Adams doing that would be a rather funny notion, wouldn’t it?” He hopes that she will get beyond the Greenwich Village esthetes and find writers of genuine value. He mentions Floyd Dell, formerly the literary editor of the Chicago Evening Post, who in 1913 had come to New York to edit the Masses: “You will remember how we used to follow everything he said. I always thought there was something missing in him. He got us started reading Dreiser, you know. Do you suppose you will see Dreiser?”

Sidney’s next letter, written in two installments, is much longer, detailing what he calls his “Chicago adventure.” He writes the first part on the train returning home from Chicago, where he had gone to see about some improvements to the Adams pump. While there he went into a bookstore that was “the strangest place I have ever been in…a tiny room, hardly larger than the bathroom at our house here,” yet it excited him because it seemed to be “a hangout for political, religious and philosophical radicals.” Two men were there arguing–one “a heavy-featured, long-jawed man” and the other a tall Irishman with “the loose, somewhat slack mouth of the orator” and beautiful hands. The Irishman left after angering the other man, who, with “a bulldozing air about him,” called the Russian revolution “the greatest experiment for human freedom ever made” and, Sidney observes, “seemed somewhat sentimental on the subject of labor.” The proprietor, “a slender, sick-looking man,” afterwards identified the Irishman as Jim Larkin, controversial Irish labor leader, and the other man as Carl Sandburg, whose Chicago Poems (1916), Sidney recalls, “I got excited about a year ago, although, as I remember, you did not.”

While at the bookstore, he also met the proprietor’s blind wife and their daughter:

We were speaking of books and once the daughter, who at fourteen seemed to have read everything, turned to speak to me and at the same time tried to thrust a newly lighted cigarette into her mother’s mouth. She made rather wild stabs at the spot where her mother sat and struck her on the nose, the cheek and the forehead before the cigarette had found its way to its natural resting place.

They all laughed good naturedly over this rather grotesque incident and that permitted me to laugh with them.

In a “romantic” impulse, Sidney avoided revealing to these people his occupation as a pump manufacturer and, instead, told them that, like the family in “The Egg,” he left a chicken farm to come to town. His ambition, he told them, is to start a bookstore. The proprietor replied that he had been a minister in a Wisconsin before becoming a radical in “politics, religion, love and philosophy.” In the course of their conversation a policeman came in the shop to buy pamphlets by Robert Ingersoll and Clarence Darrow, and then they were joined by a young man who began a discussion of eroticism in modern fiction with the proprietor’s daughter. The girl, “talking eagerly, thrusting her body forward on the box on which she was seated,” made comments about relationships between men and women that, Sidney notes, left him “breathless” and feeling like “a thorough backwoodsman.”

Sidney buys two books–Waldo Frank’s Our America (1919) and Van Wyck Brooks’ America’s Coming of Age (1915)–and a ticket to a lecture that evening by the blind woman at the Dill Pickle, an actual speakeasy on the Near North Side, run by Jack Jones, a former labor organizer.3 Again resorting to duplicity, he wires Hallie that he is detained overnight by business. On the train going home the next day, he writes that he has begun reading The Education of Henry Adams and suggests that “there is another Adams, one Sidney Adams, who will be educated a little here.” He confesses, however, to a certain disappointment that “The poets, the new ones, I am afraid, do not look like the poets of our dreams,” and adds that “The poet Sandburg did smoke such awfully rank cigars.”

A day or so later, Sidney writes a long second installment of the letter from his office when “everyone but me is gone and I can just sit here, sometimes for hours, and have fancies.” After acknowledging feelings of guilt over his “innocent lie” to Hallie about having to stay overnight for business, he continues his account of his experience in Chicago. Arriving at the Dill Pickle, he entered “a long low room” where, in addition to the bookseller, his wife and daughter, seven people with “rather dull faces” sat waiting. The owner of the Dill Pickle invited Sidney to a meeting at which a Madame Freiburger was to speak on “Men who have made love to me.” A fat man introduced the blind woman as “the best mind on intellectual things of anyone in America,” and then sat down and dozed off.

The woman spoke on Dostoevsky, and by the time she finished, Adams writes, “I suppose I and the husband and the rowdy daughter, now sitting with her hands crossed and looking very demure and solemn, were the only ones in the audience not asleep.” Afterwards, Adams invited the three of them out to dinner. On the way the daughter spoke of marriage, stating “in a matter of fact tone” that she had no interest in marrying but that “In a year or two” she would “go in for some experimenting with lovers.” Later in the restaurant she spoke to him about her interest in Russia: “I will never be an intellectual like Mother and so I should be a woman of action. I wish I lived in Russia now. I would like nothing better than the chance to get out and fight for the liberation of the proletariat.”

After dinner they went to the family’s two-room apartment, which was strewn with “Smelly vegetable tins, an overflowing garbage can, women’s underwear lying about on chairs and even on the table among the unwashed dishes of the last meal.” Despite the mess Sidney observes that he felt oddly happy.

Just why I can’t say, dear sister. Is there something in me, a New England Adams, deeply at war with the notion of being an Adams and a son of New England? I wondered. “Is there something of the same sort in Cynthia too?” I asked myself. “Is that why she wanted to run off to New York and live in Greenwich Village?”

The blind woman began again to talk about Russian writers, this time with “an odd sort of fire and swing to everything she said” that had been lacking at the Dill Pickle, asserting that “the Russians had revolutionized all Western thought.” For the next three hours, he writes, “she ruled like a queen over the three other minds in the room and then I went stumbling down the dark stairway and after some little trouble found an elevated station from where I could take a train back into the Loop and back into the tone of the life I have always known.” The narrative ends at this point, and thus we never learn the ultimate fate of either of the Adamses, although Anderson in his introduction indicates that later on Cynthia is still living in New York when he meets her there, and he has established a close friendship with Sidney, frequently exchanging visits with him in La Salle and Chicago.

Dating the “Letters to Cynthia” is difficult because Anderson apparently made no mention of the work elsewhere, but a few internal clues would suggest a date of around 1920 or ’21. Of the books Sidney Adams mentions, the latest is Waldo Frank’s Our America, which appeared in late 1919. The time period of the story, however, may be somewhat earlier. In November 1920 the Radical Book Shop, located at 826 North Clark Street and clearly the model for the store Sidney visits, held an exhibition of Anderson’s paintings. The owners at that time were Thiem and Netta Cooper. On November 12, 1920, Anderson wrote that his show of watercolors was going on and that “there is a good deal of discussion as to whether I am insane, decadent, or a new note.”4 Many years later, Netta Cooper crustily recalled Anderson’s “bloody” paintings and his frequent visits to the store when he was “usually…displeased with [the] way his books were displayed–that is, not well, because [they were] not selling.”5

The Coopers, however, had only recently bought the shop and were not the models for the family described in “Letters to Cynthia.” Howard Udell, formerly a Unitarian minister, and his wife Lillian, who was blind, began the Radical Book Store in 1914. True to its name, it specialized in radical publications, and Sandburg and Larkin did in fact often go there. The Udells had two daughters, Phyllis and Geraldine. The younger one, Geraldine, appears to be the one Anderson depicted in “Letters to Cynthia.” In an interview in 1963 she recalled taking modern dance classes and piano lessons with Tennessee Mitchell, Anderson’s second wife. For the latter she went to the Andersons’ apartment on Division Street. She added that she knew Sherwood and enjoyed talking with him. She later became the business manager of Poetry magazine.6

Although Anderson was impressed by The Education of Henry Adams, which he first read in December 1918, and would go on later to include numerous allusions to it in his own autobiography, A Story Teller’s Story (1924), “Letters from Cynthia” shows little direct influence of it beyond the general theme of broadening one’s cultural horizons. Anderson in fact felt that his own region had certain advantages over Adams’s New England, asserting that “We do, I am sure, both live and die rather better in the Middle West. Nothing about us is as yet so completely and racially tired.”7 In an article published in 1918, a year after Anderson’s first visit to New York, he criticized writers and artists there as too ingrown and elitist: “In New York, when artists began to gather in groups about Washington Square, when Greenwich Village became their abiding place, the chance for a distinctive Manhattan literature went to the bow-wows.” In contrast, he wrote, Chicago writers and artists are fortunate to live in a city that is “sprawled out over the prairies” and, in going back and forth, they “rub elbows with the laborer, the clerk, the professional and business men.”8

Thus there is something that Anderson considers healthy and typically Midwestern in the mingling that takes place in “Letters to Cynthia” between the small-town manufacturer and the radical literary crowd in Chicago. However, Sidney at times seems overly impressionable, and the culture he finds in Chicago is thin. Many of the writers who had made up what Anderson called the “Robin’s Egg Renaissance”9 of previous years, such as Dell, Burton Rascoe, Margaret Anderson, Max Bodenheim, and Ernest Hemingway, were gone. Jim Larkin by November of 1920 was in prison in New York. Even though Sandburg was still around, he seems, as presented in “Letters,” rather affected. Sidney’s evening at the Dill Pickle is unappealing, although he does enjoy the woman’s stimulating talk at the house afterwards.

The story was left unfinished perhaps in part because Anderson was unsure of how to proceed with either Sidney or Cynthia. Eventually they would both likely tire of too much exposure to the excesses of those whom Anderson called the “Little Children of the Arts,”10 and even though Sidney may have outgrown the provinciality of LaSalle, he continues to enjoy the closeness of nature there.

Another factor that may have prevented the completion of the story was Anderson’s own mixed feelings toward city vs. country life. He was well aware of the advantages and drawbacks of both, but in 1920 his movements were for the most part away from the city as he spent the winter in Fairhope, Alabama, and the summer at Ephraim, Wisconsin, traveled frequently during the year to Owensboro, Kentucky, and moved in the fall to Palos Park, a small village near Chicago. After he left the Chicago area in 1922, he lived in New York, Reno, and New Orleans, then in 1926 settled in southwestern Virginia, spending much of the summer at his country home, Ripshin, and the small town of Marion. But he also traveled widely and stayed often in New York. Ultimately, it was in a balance of both city and country that Anderson himself found most satisfaction. Like Sidney Adams, he enjoyed them both in turn and knew, when he had enough of one, to light out for the other.


1. Quotations from “Letters to Cynthia” are used with the permission of the Sherwood Anderson Literary Estate Trust and the Newberry Library.
2. Privately printed in 1907 and published by Houghton Mifflin in 1918.
3. Anderson wrote about Jones in “Jack Jones-The Pickler,” Chicago Daily News, June 18, 1919, p. 12; and in Sherwood Anderson’s Memoirs, ed. Ray Lewis White (Chapel Hill: Univ. of North Carolina Press, 1969), 356-69.
4. Letters of Sherwood Anderson, ed. Howard Mumford Jones and Walter B. Rideout (Boston: Little Brown, 1953), 64.
5. Dale Kramer, Chicago Notebooks, Newberry Library.
6. Kramer Notebooks.
7. Letters, 43.
8. “Chicago Culture,” Chicago Daily News, Feb. 20, 1918, p. 7.
9. Memoirs, p. 317.
10. Memoirs, p. 347.