On 4 May 1885 Redpath replied to Clemens’s proposal: “Now about the auto. When I do work by the week, I charge $100 a week for the best I can do. I have had a run of ill-luck lately but I found that that was what I averaged. It wd take you much less time than you think. I get you word for word & it takes a long time to write out.” Clemens accepted these terms and urged Redpath to come to Hartford soon. “I think we can make this thing blamed enjoyable.” It is clear that he was beginning to intuit the need for a responsive, human audience when dictating—something he articulated quite clearly six years later in a letter to Howells.27

The two men began working together sometime in mid-May and continued for several weeks. In the six dictations that survive, Clemens traced the history of his friendship with Grant, then talked about his own protégé, the young sculptor Karl Gerhardt, who had a commission to create a bust of Grant. In the longest of these dictations he launched into a detailed account of how he had acquired the right to publish Grant’s Memoirs, defending his tactics and countering newspaper insinuations that he had acted unethically.

Clemens probably stopped dictating shortly before Grant died on 23 July 1885.28 In July and August (and possibly earlier) Clemens read over some of the typescripts that Redpath had created from his stenographic notes, adding his own corrections here and there but making few changes in wording. He found the result far from satisfactory, as he implied in a letter to Henry Ward Beecher:

I will enclose some scraps from my Autobiography—scraps about Gen. Grant—they may be of some trifle of use, & they may not—they at least verify known traits of his character. My Autobiography is pretty freely dictated, but my idea is to jack-plane it a little before I die, some day or other; I mean the rude construction & rotten grammar. It is the only dictating I ever did, & it was most troublesome & awkward work.29

Redpath’s work as an amanuensis was unskillful. None of his stenographic notes are known to survive, but his typescripts are manifestly ill-prepared—full of typing errors, struck-over characters, and extraneous marks—and his numerous penciled corrections create punctuation that is in no way characteristic of Clemens’s own habits.

No manuscripts for the autobiography written between 1885 and 1890 have survived, but the project was certainly not forgotten. In late 1886 as he worked on A Connecticut Yankee in King Arthur’s Court, Clemens wrote to Mary Mason Fairbanks: “I fully expect to write one other book besides this one; two others, in fact, if one’s autobiography may be called a book—in fact mine will be nearer a library.” His 1876 plan for a work not limited “as to space” was evidently alive and well. And in August 1887, two years after halting the Grant Dictations, Clemens wrote to his nephew, “I want a perfect copy of Fred Grant’s letter, for my Autobiography. I was supposing I had about finished the detailed private history of the Grant Memoirs, but doubtless more than one offensive chapter must be added yet, if Fred Grant lives.” A few months earlier he told another correspondent, “No, I’ll leave those details in my autobiography when I die, but they won’t answer for a speech.”30

Then, in December 1887, Orion wrote to ask his brother’s permission to reveal “something of your boyhood” in an upcoming interview with a local journalist. He listed a few “points” he wanted to offer:

I thought of mentioning Grandpa and Grandma Casey; some younger and older characteristics of ma (fondness for or tenderness for animals, &c.); pa’s studying law under Cyrus Walker; their marriage and removal to Tennessee; pa’s treatment of the strange preacher about the cow; his facing down the old bully, Frogg; his settling a dispute before him as justice of the peace with a mallet; your philosophical dissatisfaction with your lack of a tail; your sleep-walking and entrance into Mrs. Ament’s room; your year’s schooling; your quitting at 11; your work in my office; your first writing for the paper (Jim Wolf, the wash-pan and the broom); your going to Philadelphia at 17 . . . ; your swimming the river and back; ma’s complaint that you broke up her scoldings by making her laugh; Pa’s death; his sharp pen writing for the paper; her present age and vigor; fondness for theatre.31

Clemens had already used a number of these “points” in published work. His making wicked fun of Jim Wolf’s pointless rescue of a wash-pan and broom from the threat of a fire next door was in fact his “first writing” for Orion’s Hannibal newspaper, “A Gallant Fireman” (1851).32 And in the first chapter of Tom Sawyer Aunt Polly (based on Jane Clemens) had mildly complained that Tom knew that if he could “make me laugh,” her anger toward him would disappear. Still, Clemens refused Orion’s request:

I have never yet allowed an interviewer or biography-sketcher to get out of me any circumstance of my history which I thought might be worth putting some day into my AUTObiography. . . .

I have been approached as many as five hundred times on the biographical-sketch lay, but they never got anything that was worth printing.33

Clemens would make use of only a few of these “points” in the autobiography. But his stinginess about letting others reveal the raw materials of his history is certainly understandable, and it may suggest that at this time in 1887 he still intended to write an autobiography that would include these anecdotes from his early life.

By the fall of 1890, Clemens had been investing money in the typesetting machine invented by James W. Paige for almost ten years (since 1881). It was, however, still not completed. The relevance of this project to his autobiography was inescapable, and in the “closing days” of that year he began to write “The Machine Episode,” an unsparing account of the way Paige had charmed and beguiled him into an enormous investment without having yet achieved a salable product.