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Samuel Langhorne Clemens’ first meeting with President Ulysses S. Grant was less than memorable. The famed writer and humorist, better known as Mark Twain, had little in common with the stoic chief executive. As he shook hands with Grant during a visit to the White House in 1870, Clemens found himself uncharacteristically at a loss for words. After a few moments of awkward silence he said to his expressionless host, “Mr. President, I am embarrassed. Are you?” The president, Clemens later recalled, “smiled a smile which would have done no discredit to a cast-iron image and I got away under the smoke of my volley.”

Nine years later, the two met again with the same awkward result, but this time Grant said to Clemens, “I am not embarrassed, are you?” Clemens was impressed by Grant’s “good memory for trifles as well as for serious things,” and the two American standards eventually became friends. In 1884 the unlikely friendship would spawn a unique partnership.

“IF THE BOOK BUSINESS interferes with the dramatic business, drop the former, for it doesn’t pay salt,” Clemens wrote in 1884 to Charles L. Webster, his niece’s husband. Though he had recently finished writing Huckleberry Finn and started a publishing company named for and directed by Webster, Clemens was in a financial bind. The source of his troubles was a lavish lifestyle and poor investments in such dubious inventions as a “patent baby clamp,” designed to prevent infants from kicking off their blankets, and a typesetting machine that was never put into use. In November of that year, the 48-year-old Clemens reluctantly took to the lecture circuit and toured the Northeast with the popular Southern writer George Washington Cable. As one half of the “Twins of Genius,” Clemens earned about $17,000 for the 15 weeks of work. More significantly, however, he stumbled upon an opportunity that changed his life.

After lecturing in New York City’s Chickering Hall one rainy November night, Clemens was walking down the street when, as he later recalled, “two dim figures stepped out of a doorway and moved along in front of me.” Clemens overheard one of the men ask the other, “Do you know General Grant has actually determined to write his memoirs and publish them? He has said so today, in so many words.” Clemens could not believe his luck. Grant’s disastrous financial affairs were widely known, and Clemens instantly recognized the financial bonanza a publishing collaboration could mean for both men.

One of the greatest military officers the United States ever produced, Ulysses S. Grant possessed traits of loyalty and political naiveté that caused him only grief as president. During his two terms Grant had more than once been the victim of deception. By 1884, however, the Credit Mobilier, Whiskey Ring, and other scandals associated with his presidency were fading from public memory. Grant had escaped the scandals with his reputation largely intact.

Life outside the White House, however, brought Grant to the brink of ruin. After failing in a third bid for the Republican presidential nomination in 1880, Grant helped found the Mexican Southern Railroad. By 1884 the company was bankrupt. Grant scraped together $100,000 to invest in the promising Wall Street brokerage firm of Grant and Ward, in which his son Ulysses S. (Buck) Grant was a partner. Unfortunately, Ferdinand Ward’s illegal dealings soon helped destroy the firm. In 1884, at the age of 62, Ulysses S. Grant was destitute.

That summer, however, Grant entered into a new venture that held some promise for success. Century Magazine asked Grant to write a series of articles about his war experiences. Desperate for money, Grant accepted the assignment, and the $500 Century offered for each manuscript. Grand found the work relatively simple and, encouraged by the articles’ success, the two parties began to discuss terms for the publication of Grant’s memoirs.

THE MORNING AFTER HIS Chickering Hall lecture, Clemens paid a visit to the Grant home on 66th Street, where he found the general discussing Century’s proposal with his son Fred. Century President Roswell Smith had offered Grant a standard contract that would pay him 10 percent in royalties. Content with the offer, Grant was prepared to sign.

Clemens considered the contract totally inadequate, and advised Grant to hold out for better terms. According to Clemens, he suggested that Grant “Strike out the ten percent and put twenty percent in its place. Better still, put seventy-five percent of the net returns in its place.” Grant balked, thinking that Century would never agree. Clemens then made his own pitch. “Sell me the memoirs, general,” he said. He offered Grant 75 percent of the profits and said he would pay any necessary expenses out of his own quarter share. Grant, Clemens recalled, “laughed at that and asked me what my profit out of that remnant would be.” Clemens responded, “a hundred thousand dollars in six months.” The ex-president was skeptical but decided to wait before signing Century’s contract.

As he weighed Clemens’ offer, Grant commenced work on his memoirs and entertained other proposals “with larger offers than have ever been made for a book before.” After a couple of months, his friend George Childs, who was also a publisher, examined the various proposals and advised, “Give the book to Clemens.”

BY EARLY 1885, GRANT knew he was terminally ill. After trying to ignore severe pain in his throat for several months, he finally visited a throat specialist, who confirmed the general’s suspicions of cancer. Grant dedicated all of his remaining energy to completing his memoirs. Throughout the spring and much of that summer he wrote steadfastly in pencil in the quiet solitude of his home. At times he was so ill and weak that he was forced to dictate his manuscript in a rasping whisper to a stenographer. During these long months, Grant suffered from severe throat pain, neuralgia, coughing, vomiting and extreme weakness. His doctors treated his cancer primarily with cocaine and administered morphine at night to induce much needed rest. In March the general came close to death but miraculously survived and continued to write.

As Grant moved slowly but steadily toward the conclusion of his memoirs, he and Clemens developed mutual respect, trust, and admiration. Clemens was increasingly impressed by Grant’s intellect and writing ability, and Grant trusted Clemens’ literary judgment. Meanwhile, Clemens made plans to sell the finished work. He hoped to make a tidy sum of money for himself and realized the great marketing potential created by the public’s interest in Grant’s heroic battle against death, but he was also genuinely concerned about his friend’s health and the financial well-being of Grant’s family.

Clemens employed the subscription method to sell the book. Webster and Company had 16 general agents and 10,000 canvassers to market the memoirs, a virtual army of subscription agents that traveled through cities and across the countryside to visit homes personally. Each salesman was armed with a manual, largely written by Clemens, entitled How to Introduce the Personal Memoirs of U.S. Grant. Each agent also carried a prospectus showing the size of the two green and gold volumes, the title page, illustrations, table of contents and selection of bindings. To encourage sales, a few of the better salesmen were given some of the original manuscript pages bound in hard covers.

The company agents–many of whom were former soldiers dressed in faded uniforms–were trained to appeal to the hearts of potential customers, especially war veterans, by stressing Grant’s physical condition, talking up Grant’s war heroism, and stressing the high quality of the work. Clemens and Webster advised the salesmen to assume people wanted the book and that the only decision they had to make concerned the type of binding. The price of each set began at about $3.50, which could be paid with one dollar up front and the balance on delivery. More elaborately bound sets ranged in price from $4.50 to $12.50. Although by that time more practical marketing schemes were replacing the old-fashioned subscription system, it proved quite successful with Grant’s memoirs. Grant had hoped the book would sell 25,000 copies. In fact, sales of the two-volume sets eventually reached about 350,000.

In June, under the tightening grip of cancer, Grant traveled with his family to Mount McGregor, New York, to escape the city’s heat and to work in a more relaxing environment. Thousands of Union Army veterans also made the trip to Mount McGregor to catch a glimpse of their dying former commander. As they walked past his cottage, Grant acknowledged them with a nod or slight wave from the porch where he sat writing. Countless old friends, political allies, and Civil War officers from the North and South also dropped in to pay their respects.

Grant seemed almost able to put off his death, as he finished the final revisions and the preface to the book. On June 29 he wrote a letter to his wife, Julia, which he held in his coat until he died. “I had an idea that I could live until fall,” he noted grimly, “I see now that the time is approaching more rapidly.” If not for the remaining work, he wrote, he “would welcome the arrival of the Messenger of Peace, the earlier the better.” On July 14, 1885, Grant wrote of his book, “There is nothing more I should do to it now, and therefore I am not likely to be more ready to go than at this moment.”

Grant died on July 23, just days after completing his task. During a final visit with Clemens, the general, unable to speak, scrawled a note in pencil to ask if his book would make any money for his family. Clemens assured him that subscriptions were already pouring in and that his efforts had been worthwhile. The memoirs ultimately provided Julia Grant with between $420,000 and $450,000.

Clemens was quite pleased with the finished work and considered it on a level with Caesar’s Commentaries. Its emphasis was, as expected, on the Civil War, and most critics later agreed that it was a fine military work. The general wrote clearly with the preciseness of his old military dispatches and showed a more thoughtful and reflective intellect than many expected. Some even suggested that Clemens had penned the memoirs. Clemens, however, had contributed little to the writing, and he said that when Grant asked for his opinion on his work, he “was as much surprised as Columbus’s cook would have been to learn that Columbus wanted his opinion as to how Columbus was doing his navigating.”

Clemens’ success in publishing Grant’s memoirs was a high point in the writer’s career. As the sales of the volumes first began piling up, he giddily told his wife, Livy, that he was “frightened at the proportions of my prosperity,” and that “it seems that whatever I touch turns to gold.” Clemens, however, who had made more than his share of bad business decisions, later claimed that the book “made money for everyone concerned but me.”

Webster and Company’s earnings from Grant’s memoirs exceeded $150,000, a substantial sum in the 1880s. The company’s profits, of course, did not all go to Clemens, but the sales of the books brought him approximately $63,000. Clemens put some of it back into the company, but also continued to pour much of his income into the development of inventor James W. Paige’s typesetting machine. By 1887 Clemens had already spent more than $50,000 on this “mechanical marvel,” as he once called it, and was still spending $3,000 a month on it. Clemens did not give up on the machine until 1894, after nearly 15 years of futile investment.

In the years following the success of Grant’s memoirs, Charles L. Webster and Company fell on hard times. The company published books by Civil War Generals Phillip Sheridan, George McClellan, and William T. Sherman and remembrances by the wives of Generals George Armstrong Custer and Winfield Scott Hancock. Civil War memoirs and narratives, however, had declined in popularity and sales lagged. The company’s fortunes received another blow in 1887, when famed clergyman and editor Henry Ward Beecher died just three weeks after signing on to write his autobiography. Webster and Clemens were left with an incomplete manuscript and an estimated loss of $100,000. At about the same time, company bookkeeper Frank M. Scott was caught after embezzling $25,000, only a portion of which was recovered.

Charles Webster retired in 1888 and sold his interest to Fred Hall, who had joined the company two years earlier. The Panic of 1893 proved to be the last straw for the struggling firm. Banks and businesses across the country closed by the score, and creditors filed claims against the foundering Charles L. Webster Company for almost $80,000. The company failed in 1894, and Clemens filed for bankruptcy. Embittered by his publishing experience, Clemens blamed all of his company’s problems on Hall and Webster, whom he had grown to hate. After several years of writing and lecturing he managed to pay off his remaining debts and reestablish his substantial annual income, which in 1902 amounted to more than $100,000.

In his autobiography, published posthumously in 1924, Clemens described his brief and rather comical Civil War career. He had lasted just two weeks in the Confederate service in 1862 before claiming he was “incapacitated by fatigue” and “resigning.” It is remarkable that Clemens, who claimed to know “more about retreating than the man who invented retreating,” ever became friends with the iron-willed “Unconditional Surrender” Grant. Ultimately, however, he decided that Grant was like himself, “just a man, just a human being, just an author.”

Craig E. Miller is a retired history teacher from Pennsylvania.