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From The Life of Mark Twain: The Early Years, 1835-1871, page 84

But Sam had no future in Muscatine. For that matter, neither did Orion. He was half owner of a Whig newspaper, but as soon as he settled there, he had changed his party affiliation from Whig to Republican to signal his opposition to the Kansas-Nebraska Act.' The act effectively repealed the Missouri Compromise and opened the western territories to “popular sovereignty —that is, to settlement by slaveholders. Opponents of slavery, including Orion, were outraged, and passage of the act led inexorably to border ruffians like William Quantrill and to the rehearsal for the Civil War in “bloody Kansas.”

Sam returned to St. Louis:  From The Life of Mark Twain: The Early Years, 1835-1871, page 86:

Sam resided in a boardinghouse at the corner of Fourth Avenue and Washington Street owned by the Pavey family, relatives of Hannibalians. “It was a large, cheap place & had in it a good many young fellows who were students at a Commercial College,” he remembered. His roommate, Jacob Burrough, was a journeyman chairmaker, a rabid republican and autodidact “fond of Dickens, Thackeray, Scott & Disraeli” and the model for the character of Barrow in The American Claimant (1892), “a short man about forty years old, with sandy hair, no beard, and a pleasant face badly freckled but alive and intelligent, and he wore slop-shop clothing which was neat but showed wear.” Sam and Burrough seem to have bonded over books, Sam remembered that his roommate was the only other lover of literature in the house. Twenty-two years later Sam conceded that at the time he had been “a callow fool, a self-sufficient ass, a mere human tumble-bug, stern in air, heaving at his bit of dung, imagining that he is remodeling the world and is entirely capable of doing it right. . . . Ignorance, intolerance, egotism, self-assertion, opaque perception, dense & pitiful chuckle-headedness—& an almost pathetic unconsciousness of it all, That is what I was at 19-20,”

See SLC to Jacob H. Burrough, 1 Nov 1876, Hartford, Conn. (UCCL 01384). 2022.

From Page 87:

He returned to work for the Evening News, though he lasted there only a few months. “He was a good printer,” his coworker William Waite remembered, “but mighty independent.” After all, he had earned a living at his craft in busier shops and bigger cities. But he was occasionally tardy for work and Charles G. Ramsey, owner and editor of the News, badgered him. According to Waite, Ramsey “would say: ‘Here's that —— boy late again,’” the type of rebuke Sam resented his whole life. “One morning he turned on Ramsey and replied: “Take your dashed situation, and go to (a warm country)!" — or words to that effect. “He left the office and we heard nothing of him for several years.” After burning his bridges in St. Louis, Sam again fled upriver to rejoin Orion, who had recently resettled in Keokuk, Iowa.”

From page 90:

Sam delivered his first public speech on January 17, 1856, at a printers’ banquet at the Ivins House, the best hotel in Keokuk, to celebrate the sesquicentennial of the birth of Benjamin Franklin. Unfortunately, no transcript of the address survives, though Orion described it in the next issue of the Keokuk Gate City as “replete with wit and humor,” adding that it had been “interrupted by long and continuous bursts of applause.” One of Sam's coworkers also remembered the occasion: “Blushing and slowly getting upon his feet, stammering in the start, he finally rallied his powers, and when he sat down, his speech was pronounced by all present a remarkable production of pathos and wit, the latter, however, predominating, convulsing his hearers with round after round of applause.” Sam was soon recruited to join a local debating society. Meanwhile, the printing of the city directory that he supervised, issued in June 1856, “did not pay largely,” according to Paine, because Orion “was always too eager for the work; too low in his bid for it.” Sam listed his own occupation in it as an “antiquarian.” The term is significant because, in one of his columns in the Hannibal Journal in May 1853, he had mentioned the recent discovery of “ruins of ancient cities” in Mexico—no doubt the allegedly lost Aztec city of Iximaya—that was the subject of Pedro Velasquez's fanciful Memoir of an Eventful Expedition in Central America (published in English in 1850). He added that the news would interest an “antiquarian,” his word for a type of explorer or anthropologist.”

Predictably, then, when Sam came across a copy of William Herndon’s Exploration of the Valley of the Amazon (1854) in Keokuk, he was excited and intrigued. A passage about coca, an unregulated drug sometimes used in patent medicines, galvanized his interest.

From page 91:

“I was fired with a longing to ascend the Amazon” and “to open up a trade in coca with all the world,” he remembered. He nursed an ambition to explore the headwaters of the Amazon—or, more accurately, to exploit the narcotic effects of the coca plant for profit.” He conspired in the scheme with a pair of potential partners, one of them Joseph S. Martin, a local Keokuk doctor and faculty member at Iowa Medical College. He also tried to entice his nineteen-year-old brother Henry to join the expedition, but Henry first asked his mother's permission and approval. “If I have an opportunity to go, I am afraid it will not be easy to obtain Ma's consent,” he advised Sam, and then he offered his own scrap of advice: “You seem to think Keokuk property is so good to speculate in, you'd better invest all your spare change in it, instead of going to South America.” In the end, Sam left Keokuk alone.”

He embarked on his quixotic journey sometime before mid-October 1856. Later, in a characteristic embroidery of the facts, he claimed that he discovered a fifty-dollar banknote blowing in the wind that financed his excursion—“I advertised the find and left for the Amazon the same day,” lest the owner claim the note—but no evidence corroborates this story.” Instead, Sam seems to have agreed to contribute a series of essays to the Keokuk Saturday Post for which he would be paid five dollars apiece. They were the first articles for which he was ever compensated. He boated south to St. Louis and, on October 13, he walked through the St. Louis Agricultural and Mechanical Association Fair and wrote up his observations of the “happily spent day” for the paper. Three of the next four pieces he sent the Saturday Post were published under the Dickensian pseudonym “Thomas Jefferson Snodgrass”—the nom de plume may allude to Jefferson's auburn hair, the same color as Sam's. Thomas Rees, son of George Rees, editor of the Saturday Post, boasted years later that his father had “discovered” Mark Twain. According to the son, “The firm of Kees & Son arranged with the young man to write some articles for publication in the Keokuk Post, which they mutually agreed would be worth five dollars each.” After submitting one or two from St. Louis, Sam demanded an increase in pay and Rees met his demand. He then submitted three more columns from Cincinnati and upped the ante by demanding ten or fifteen dollars for any additional columns. George Rees refused to meet his price and, as Thomas Rees put it, “the series of articles ended at that point.” Sam had overpriced his wares.

From page 92:

The second Snodgrass letter recounts his “voyage” from St. Louis to Cincinnati, Rather than rail directly from St. Louis to Cincinnati or catch a steamboat downstream to Cairo and up the Ohio River, however, Snodgrass (that is, Sam) took a much more circuitous route—from St. Louis to Keokuk in mid-October to see Rees and negotiate payment for the Snodgrass letters, back downstream to Quincy, then by rail to Chicago and Indianapolis, finally arriving in Cincinnati about October 24. He found work in the print shop of T. Wrightson & Co. on Walnut Street and a room in a boardinghouse three blocks away on Third Street. With five daily and fifteen weekly news- papers and a population of about 150,000, the Queen City was a publishing -enter for the western United States, with a lucrative job market for printers, Ironically, twenty-year-old W. D. Howells worked for a time a block away from Sam, though the two men would not meet formally for thirteen more years. Sam's fellow boarders were, he remembered, “commonplace people of various ages and both sexes. They were full of bustle, frivolity, chatter and the joy of life and were good-natured, clean-minded and well-meaning; but they were oppressively uninteresting, for all that—with one exception.”** He soon befriended the exception, a Scot whom he later called Macfarlane—in fact, probably John J. McFarland, who was not only Sam's fellow boarder but his coworker at Wrightson & Co, Macfarlane was a “diligent talker” about “forty years old—just double my age—but we were opposites in most ways and comrades from the start.’ ‘The winter of 1856-57, Sam reported in his third Snodgrass letter, was one of the harshest on record. (The coldest winter he ever spent was a winter in Cincinnati?)

... Ward and I have held a long consultation, Sunday morning, and the result was that us two have determined to start to Brazil, if possible, in six weeks from now, in order to look carefully into matters there ... and report to Dr. Martin in time for him to follow on the first of March. We propose going via. New York. Now, between you and I and the fence you must say nothing about this to Orion, for he thinks that Ward is to go clear through alone, and that I am to stop at New York or New Orleans until he reports. But that don’t suit me. My confidence in human nature does not extend quite that far. I won’t depend upon Ward’s judgment, or anybody’s [else.—]I want to see with my own eyes, and form my own opinion.

SLC to Henry Clemens, 5 Aug 1856, Keokuk, Iowa (UCCL 00012).”

No letters have been recovered for the next ten months. Dissatisfied with his position in Orion Clemens’s mismanaged Ben Franklin Book and Job Office and hoping to venture profitably into Brazil, Clemens decided to abandon Keokuk. His own account of his departure, elliptical and influenced by time and imagination, occurs in his autobiography:

One day in the midwinter of 1856 or 1857—I think it was 1856—I was coming along the main street of Keokuk in the middle of the forenoon. It was bitter weather—so bitter that that street was deserted, almost. A light dry snow was blowing here and there on the ground and on the pavement, swirling this way and that way and making all sorts of beautiful figures, but very chilly to look at. The wind blew a piece of paper past me and it lodged against a wall of a house. Something about the look of it attracted my attention and I gathered it in. It was a fifty-dollar bill, the only one I had ever seen, and the largest assemblage of money I had ever seen in one spot. I advertised it in the papers and suffered more than a thousand dollars’ worth of solicitude and fear and distress during the next few days lest the owner should see the advertisement and come and take my fortune away. As many as four days went by without an applicant; then I could endure this kind of misery no longer. I felt sure that another four could not go by in this safe and secure way. I felt that I must take that money out of danger. So I bought a ticket for Cincinnati and went to that city. 

Actually, Clemens left Keokuk in October 1856, not in “midwinter.” He made a brief visit to St. Louis, where he evidently attended the opening day, 13 October, of the St. Louis Agricultural and Mechanical Association Fair and wrote a sketch about it. He also wrote his first Thomas Jefferson Snodgrass letter in St. Louis, on 18 October.

Having spent about a week with his mother and sister, Clemens left St. Louis. It is likely that he departed on 18 October and arrived in Keokuk the following day.  He then went on by river packet to Quincy, Illinois, then by train through Chicago and Indianapolis to Cincinnati, probably arriving on 24 October. There he found employment at T. Wrightson and Company, one of the city’s leading printers, where he continued to work into the spring of 1857.

See  "Mark Twain in Cincinnati: A Mystery Most Compelling" by William Baker for speculations of Sam Clemens' activities in Concinnati.  From pages three and four:

 Clemens's official biographer, Albert B. Paine, says Clemens had planned to go directly to Cincinnati from St. Louis, "but a new idea--a literary idea--came to him and he returned to Keokuk." Where did he get the money for that steamer trip and the subsequent train passage to Cincinnati? Perhaps he found fifty dollars, as he reports, although he might have borrowed it from his sister Pamela's husband, William A. Moffett, with the request to keep it a secret; hence the invention of finding fifty dollars. River travel to Cincinnati via Cairo and then east on the serpentine Ohio River, a distance of 600 miles, would have cost only nine dollars, while the trip by railroad via Terre Haute and Indianapolis, a distance of 350 miles, would have cost about fifteen dollars.  But parts of the Ohio were too low for steamers in the fall of 1856, though he probably could have made a steamer trip as far as Louisville. And although the trip by railroad would have necessitated three changes of rail lines (the direct 322-mile route was not open until April 1857), the rail route was clearly the logical alternative. He ended up by taking a crazy zig-zag route that cost about thirty dollars (about $25.24 fare plus food, hotel, and porterage). It was a sizeable expense for a man who had been working for five dollars a week plus room and board, even more remarkable since he claims he never got any money at all. 

 Now it is the dating that concerns us. If I am correct in guessing that Clemens took the Snodgrass letter to Keokuk on the day after it was written, he would have arrived on 19 October. In his eagerness to see Rees he would not have waited longer.  Fred Lorch says he spent "a day or two" in Keokuk.  If we say two days, 20 and 21 October, that would put him on the river packet to Quincy on 22 October, arriving by train in Chicago that night, where he stayed in "the Massasawit House," entraining for Indianapolis on the 23rd. Then he took "the midnight thunder and lightning train" from Indianapolis to Cincinnati, arriving on the morning of 24 October 1856. If my assumptions are correct, he arrived in the center of the western publishing industry about five weeks before his twenty-first birthday on 30 November.

On 15 April 1857 Clemens took passage for New Orleans on the packet Paul Jones. Probably the “great idea” of the Amazon journey was still alive in his mind as he later claimed, but within two weeks his old ambition to become a Mississippi pilot was rekindled. During daylight watches he began “doing a lot of steering” for Horace E. Bixby, pilot of the Paul Jones, whose sore foot made standing at the wheel painful. Bixby (1826–1912), later a noted captain as well as pilot, recalled after Clemens’s death:

I first met him at Cincinnati in the spring of 1857 as a passenger on the steamer Paul Jones. He was on his way to Central America for his health. I got acquainted with him on the trip and he thought he would like to be a pilot and asked me on what conditions he could become my assistant. I told him that I did not want any assistant, as they were generally more in the way than anything else, and that the only way I would accept him would be for a money consideration. I told him that I would instruct him till he became a competent pilot for $500. We made terms and he was with me two years, until he got his license.

Scharnhorst has a different date for Sam's trip on the Ohio River.  See The Life of Mark Twain: The Early Years, 1835-1871, page 93.

Sam paid a sixteen-dollar fare and on February 16, 1857, he finally left Cininnati aboard the Paul Jones, a 353-ton side-wheeler traveling from Pittsburgh to New Orleans. From there he planned to embark on the next ship sailing for Para, Brazil, and the Amazon. He described the steamboat in “Old Times on the Mississippi” as an “ancient tub,” and, following his lead, Paine described it as an “ancient little craft” and Samuel Charles Webster mocked it as the “ramshackle Paul Jones.” But Sam’s description of the ship was another example of his creative (mis)remembering. The ship had been built only two years earlier; it was piloted by one of the most respected officers on the river; and contemporary newspapers praised it as a “magnificent,” ‘first class,” and a “very staunch and pretty packet” with “finely furnished cabins’ and “superb” dining.

Bixby consistently indicated that he and Clemens came to terms either at their first meeting or quite soon after, Mark Twain designated New Orleans as the place where he approached Bixby about becoming his steersman and where they reached an agreement. Clemens’s version is the most romantic, not until the Paul Jones reached New Orleans on [26 April ?] February 28 (DBD) did Clemens learn that he “couldn’t get to the Amazon” : the obstacles were insuperable. But it is reasonable to assume that, before agreeing to instruct him, Bixby would have used the entire trip to New Orleans to test his ability at handling the wheel. It's not likely he would have done so without some idea of Clemens' intent.

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