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1852–1857: Unsuccessful writer

After having borrowed three thousand dollars from his father-in-law in September 1850 to buy a 160-acre farm in Pittsfield, Massachusetts, Melville had high hopes that his next book would please the public and restore his finances. In April 1851 he told his British publisher, Richard Bentley, that his new book had "unquestionable novelty" and was calculated to have wide appeal with elements of romance and mystery. In fact, Pierre: or, The Ambiguities was heavily psychological, though drawing on the conventions of the romance, and difficult in style. It was not well received. The New York Day Book published a venomous attack on September 8, 1852, headlined "HERMAN MELVILLE CRAZY". The item, offered as a news story, reported,

A critical friend, who read Melville's last book, Ambiguities, between two steamboat accidents, told us that it appeared to be composed of the ravings and reveries of a madman. We were somewhat startled at the remark, but still more at learning, a few days after, that Melville was really supposed to be deranged, and that his friends were taking measures to place him under treatment. We hope one of the earliest precautions will be to keep him stringently secluded from pen and ink.

On May 22, 1853, Melville's third child and first daughter Elizabeth (Bessie) was born, and on or about that day Herman finished work on the Agatha story, Isle of the Cross. Melville traveled to New York to discuss a book, presumably Isle of the Cross, with his publisher, but later wrote that Harper & Brothers was "prevented" from publishing his manuscript because it was lost.

After the commercial and critical failure of Pierre, Melville had difficulty finding a publisher for his follow-up novel Israel Potter. Instead, this narrative of a Revolutionary War veteran was serialized in Putnam's Monthly Magazine in 1853. From November 1853 to 1856, Melville published fourteen tales and sketches in Putnam's and Harper's magazines. In December 1855 he proposed to Dix & Edwards, the new owners of Putnam's, that they publish a selective collection of the short fiction. The collection, titled The Piazza Tales, was named after a new introductory story Melville wrote for it, "The Piazza". It also contained five previously published stories, including " Bartleby, the Scrivener " and " Benito Cereno ". On March 2, 1855, the Melvilles' fourth child, Frances (Fanny), was born. In this period, his book Israel Potter was published.

The writing of The Confidence-Man put great strain on Melville, leading Sam Shaw, a nephew of Lizzie, to write to his uncle Lemuel Shaw: "Herman I hope has had no more of those ugly attacks"—a reference to what Robertson-Lorant calls "the bouts of rheumatism and sciatica that plagued Melville". Melville's father-in-law apparently shared his daughter's "great anxiety about him" when he wrote a letter to a cousin, in which he described Melville's working habits: "When he is deeply engaged in one of his literary works, he confines him to hard study many hours in the day, with little or no exercise, and this specially in winter for a great many days together. He probably thus overworks himself and brings on severe nervous affections". Shaw advanced Melville $1,500 from Lizzie's inheritance to travel four or five months in Europe and the Holy Land.

From October 11, 1856, to May 20, 1857, Melville made a six-month Grand Tour of Europe and the Mediterranean. While in England, in November 1856, he briefly reunited for three days with Hawthorne, who had taken the position of United States Consul at Liverpool, at that time the hub of Britain's Atlantic trade. At the nearby coast resort of Southport, amid the sand dunes where they had stopped to smoke cigars, they had a conversation that Hawthorne later described in his journal: "Melville, as he always does, began to reason of Providence and futurity, and of everything that lies beyond human ken, and informed me that he 'pretty much made up his mind to be annihilated' If he were a religious man, he would be one of the most truly religious and reverential; he has a very high and noble nature, and better worth immortality than most of us."

The Mediterranean part of the tour took in the Holy Land, which inspired his epic poem Clarel. During the tour he visited Mount Hope, a Christian farm near Jaffa. On April 1, 1857, Melville published his last full-length novel, The Confidence-Man. This novel, subtitled His Masquerade, has won general acclaim in modern times as a complex and mysterious exploration of issues of fraud and honesty, identity and masquerade. However, when it was published, it received reviews ranging from the bewildered to the denunciatory.