His opportunity came December 16th,[331] when Montgomery, with a force of nearly one hundred men, marched upon Fort Scott, to effect the release of Mr. Benjamin Rice, who had been arrested November 16th, in violation of the by-gones-to-be-by-gones provision of the treaty of June 15th; and had not been released after the adoption of the Sugar Mound Treaty of December 6th. In this exploit a merchant of Fort Scott, Mr. J. H. Little, was killed, and his store robbed of goods amounting to about seven thousand dollars. Montgomery organized his company for this raid December 14th, and, upon invitation, Brown, Stevens, and Kagi joined in the expedition. Stevens and Kagi took part in the affair; Stevens being charged, by some writers, with having killed Little. But Brown, "with his customary dislike to serve under another," or probably, because of his higher responsibilities, took no part in the attack. He went "only as far as the rendezvous" at the Wimsett farm, where he probably received his share of the loot.

Returning on the 19th, he collected his men, and on the night of the 20th, executed his famous raid into Missouri. The party operated in two divisions—one under Brown's direction and the other under Stevens's orders. With Brown were Charles Jennison, Jeremiah Anderson, Geo. B. Gill, Kagi, and three or four others. This party was to rob the plantations of Mr. Harvey B. Hicklan and Mr. John Larue. The latter lived about three-fourths of a mile from the Hicklan home. With the Stevens party were Tidd, Hazlett, and five others. This band was to rob the places of David Cruise and Hugh Martin. Cruise, in addition to his other possessions, had a slave girl that Stevens wanted—and got—but not until after he had killed Cruise. A statement by Stevens, made at the Kennedy farm, in Maryland, furnishes all the information that exists concerning the details of the murder. He is reported as saying[332] that he went to the cabin and demanded the girl; that the old man asked him to come inside, which he thoughtlessly did, and that then the old man slipped behind him and "pulled a gun." That it then became a case of "shoot first. You might call it a case of self defense, or you might say that I had no business in there and that the old man was right."

Brown's party arrived at the Hicklan home at midnight, forced the door open, and with pointed revolvers intimidated Hicklan, and proceeded to plunder the establishment. Mr. Gill, who appears to have been in charge of the ethics of the occasion, says, that in spite of his efforts to restrain the men, they took practically everything that was in sight. "Some of our men," he said, "proved to be mere adventurers, ready to take from friend or foe as opportunity offered." This statement, by one who knew whereof he spoke, is the clearest exposition of the character of Brown's thefts that has been made. The robbery on the night of December 20, 1858, was his final transaction of that character. All of the property stolen by him during that night belonged to pro-slavery men. Therefore, Mr. Gill's knowledge that "some of their number were mere adventurers, ready to take from friend or foe as opportunity offered" could not have been derived from their conduct on this occasion. The statement is explicit evidence that Brown and his men were not moved or controlled by any sentiment relating to slavery; or by any political bias in their thefts, but that they were common thieves, operating under the protection of Free-State sentiment while they robbed and plundered Free-State men and pro-slavery men, without discrimination as opportunity offered. It may be said, in general terms, that all horses look alike to a horse thief. It is the horse, per se, that appeals to the thief, rather than the political affiliations of the owner. In the absence of competent testimony to the contrary, it would be said, promptly, of Brown, that he was an exception to this rule, as well as to all other rules, that control human actions; that he was moved by loftier motives than those which control the actions of the ordinary horse thief; that he confined his plundering to pro-slavery men, and robbed them, only, as a private duty, by and with the consent of the Almighty. But this direct evidence against him, and the men whom he controlled, is competent and quite conclusive.

It has been said that Brown made restitution to Hicklan of some of his property. But that statement belongs in the class of a long line of personal statements, that have been put forward from time to time, in palliation of the enormity of Brown's crimes, or in attempts to justify them, or in efforts to make it appear that he was engaged in an unselfish warfare against slavery. Mr. Villard swept away a lot of this rubbish by the keen logic of his exposition concerning many of the stories which were made current about the Pottawatomie matter. So this statement, about returning to Hicklan some of his property, and Mr. Gill's statement that the raid on the night of the 20th, was inspired by the "Jim Daniels story," belong in the same general class of rubbish. Mr. Hicklan stated, in 1888, that nothing that was taken was ever recovered. He said:

They did not give anything back. Brown said to me that we might get our property if we could; that he defied us and the whole United States to follow him. He and his men seemed anxious to take more from me than they did for they ransacked the house in search of money, and I suppose they would have taken it if they had found it.... What I have stated is the truth and I am willing to swear to it. I do not hold any particular malice or prejudice on account of these old transactions. Old things have passed away, but the truth can never pass away.[333]

Along with the plunder of the Hicklan home, five slaves were taken; these are said to have belonged to the "Lawrence estate" then in Hicklan's care, as administrator. Besides the negroes, he took from the Lawrence estate two good horses, a yoke of oxen, a good wagon, harness, saddles, a considerable quantity of provisions, bacon, flour, meal, coffee, sugar, etc.; all of the bedding and clothing of the negroes, Hicklan's shot-gun, overcoat, boots, and many other articles belonging to the whites. From Larue were taken five negroes, six head of horses, harness, a wagon, a lot of bedding and clothing, provisions, and, in short, all the loot available and portable.[334] Besides killing Cruise and looting the home, Stevens took, as claimed by the family, two yoke of oxen, a wagon load of provisions, eleven mules, and two horses. A mule was also taken from the Hugh Martin home.

After the robberies the two parties united at a point theretofore agreed upon, and started on the return trip to Kansas. At daylight they secreted themselves in a deep wooded ravine, where they remained until after dark, when they continued their march, arriving at Mr. Wattles's home, two miles north of Mound City, at midnight of Wednesday the 22d. Here Brown stopped until morning, having with him the slaves, one wagon, and two or three of his men; the others pushing on northward with the swag, to get it beyond danger of recovery, and to divide it or sell it for the benefit of all concerned.

The liberation of the slaves was a cumbersome and dangerous experiment, but it was as necessary as it was dangerous. To have taken all this plunder and carried it off without the diversion of taking the slaves with him, would have been a case of such plain stealing, that Brown would have been completely discredited therefor; even the "Secret War Committee" might have joined in the general repudiation of him that would have followed. But the carrying off of the slaves to freedom, in this wholesale spectacular way, was great advertising; it distracted attention from the basic motive of the raid, and secured creditable notoriety for Brown in the North. It seems, however, that after arriving at the Wattles home with the slaves, Brown practically, or personally at least, abandoned them to their fate. The narrative states:[335]

At dawn on Thursday, the caravan started again, and this time without Brown. Two of his men accompanied the one ox-team, which was sent forward, one going ahead to act as pilot.

This man, however, turned back, leaving the negroes to make their way to Osawatomie alone. They arrived, without any mishap, at the home of Mr. Adair, near Osawatomie, on Christmas Eve, where, it seems, no arrangements had been made to receive them. On the arrival of the slaves at his home, Mr. Adair says he referred the matter of sheltering them to his wife, calling her attention to the responsibility it would involve. "She considered the matter a few moments and then said: 'I cannot turn them away.' They were taken around to the back yard, and the colored people were brought into the back kitchen and kept there that night."[336] Continuing the narrative Mr. Villard says that at two a. m. of the morning after Christmas, the fugitives were finally placed in an old abandoned preëmption cabin on the south fork of the Pottawatomie, where kind neighbors brought them food and gave them encouragement.[337] In this location they remained until they were taken north. It is probable that Brown, in his selfishness, cared but little whether these negroes were returned to slavery or not. He had done his stunt in liberating them, and made no pretense of defending them or of caring for them until in January, and took care not to be near the fugitives while the pursuing bands were scouring the country in search of them.