The story was first published in The Strand magazine in November 1891. Conan Doyle later ranked the story seventh in a list of his twelve favourite Sherlock Holmes stories.
A young Sussex gentleman named John Openshaw has a strange story: in 1869 his uncle Elias Openshaw had suddenly come back to England to settle on an estate at Horsham, West Sussex after living for years in the United States as a Planter in Florida and serving as a Colonel in the Confederate Army.
Not being married, Elias had allowed his nephew to stay at his estate. One strangeness is that although John could go anywhere in the house he could never enter a locked room with his Uncle's trunks. A second strangeness was in March 1883 a letter postmarked from Pondicherry, India arrived for the Colonel inscribed only "K.K.K." with 5 orange pips (seeds) enclosed.
More strange things happened: papers from the locked room were burnt and a will was drawn up leaving the estate to John Openshaw. The Colonel's behaviour became bizarre-he would either lock himself in his room and drink or he would go shouting forth in a drunken sally with a pistol in his hand. On May 2, 1883 he was found dead in a garden pool.
On January 4, 1885 Elias's brother Joseph receives a letter postmarked Dundee with the initials "K.K.K" and instructions to leave papers on the sundial. Despite his son's urging, Joseph Openshaw refuses to call the police. Three days later, Joseph Openshaw is found dead in a chalk-pit. The only clue John Openshaw can furnish Holmes is a page from his Uncle's diary marked March 1869 in which pips have been sent to three men, of whom two flee and the third has been "visted".
Holmes advises Openshaw to leave the diary page with a note telling of the destruction of the Colonel's papers on the garden sundial. After Openshaw leaves, Holmes deduces that from the time between the letter mailings and the deaths of Elias and his brother that the writer is on a sailing ship.
Holmes also recognizes the "K.K.K" as Ku Klux Klan, an anti-Reconstruction group in the South until its sudden collapse in March 1869 -- and theorizes that this collapse was the result of the Colonel's taking their papers.
The next day there is a newspaper account that the body of Openshaw has been found in the Thames River and believed to be an accident. Holmes checks sailing records of ships who were at both - Pondicherry in January/February 1883 and at Dundee in January 1885 and recognizes a Georgia bark named Lone Star--named after Texas, a Confederate State. Furthermore Holmes confirms that the Lone Star had docked in London a week before.
Holmes then sends five orange pips to the captain of the Lone Star and has the police send a cable to Savannah that the Captain and two mates are wanted for murder. The Lone Star never arrives in Savannah; there are severe gales that year and the only trace of the bark is a signpost marked "L.S." sighted in the waves.
The story is clearly one of Holmes' manifest failures. As he berates himself, he had failed to protect his client, letting him go out to his death in the rainy London night - and though Holmes eventually solved the mystery, there were no practical consequences since the bark would have drowned anyway. Likewise a plot hole is what proof Holmes can show a jury that the Captain and his mates have committed three murders?
In "The Five Orange Pips", Holmes mentions that he has been beaten four times, three times by a man and once by a woman. Since "The Five Orange Pips" is set in September 1887, before "A Scandal in Bohemia", which is set in March 1888, the woman Holmes mentions who beat him cannot be Irene Adler if the chronology is correct. However, most Holmes fans consider this to be a chronological error on Doyle's part, as "The Five Orange Pips" was published after "A Scandal in Bohemia". Doyle had made clear chronological mistakes in other Holmes stories, and no other woman is mentioned to ever be held in the same regard by Holmes or to have beaten Holmes. Also, in "A Case of Identity", Watson mentions that Adler is the only person he has ever known to have beaten Holmes. For these reasons, most Doyle fans believe Adler to be the woman mentioned in "The Five Orange Pips".
In fact, at the time, the Ku Klux Klan was already decisively broken by the U.S. authorities, with its revival in 1915 still long in the future - and even at its peak, it never had the ability to strike so far away from the U.S. South.
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