Oklahoma Historical Society Microfilm #CHN94, Cherokee Nation(Tahlequah District)Prison and High Sheriff,Undated and December 3, 1874 - December 10, 1879

Letter of Sheriff Sixkiller to Charles Thompson, Principal Chief of Cherokee Nation, October 1877
ABSTRACT
"The prisoners are obedient, orderly, and industrious, almost without exception – only two attempts to escape have occurred during the passed[sic] year. The first of which was one named "Watt" from Tahlequah District, sentenced for felony for a term of four years. Escaped guard while outside Prison walls as work on August the 16th, 1877 and was recaptured in Illinois District and returned to Prison on the 28th October 1877 and agreeable to the law has had his term of imprisonment extended for the additional term of three (3) years by authority of the court first sentencing him for the offense of escaping from prison."

"The other prisoner was "Dirt Seller" who was under sentence of death from Saline District to be executed by hanging on the 18th of October 1877 – his attempt to escape was in company with convict "Wilson" on the 9th day of October 1877 on which day as usual the guard was escorting them up from the lower cell when on entering the door at the bottom of steps the door was slammed ___[?] by the prisoners in the face of the guard who being quite near behind, pistol in hand, threw his left arm in preventing the entire closing of door and in a little while pried open far enough to look through when he observed "Dirt Seller" in the act of sliping[sic] shackles (which ___[?] had been loosened) off of his ankles, not being able to push open the door, nor to release himself, the guard was compelled to use his weapon and did by shooting "Dirt Seller" in the hip while he was stooping over working at his shackles upon the guard firing the one shot, both convicts flung open the door and came rushing toward the guard who while retreating backward fired again shooting "Dirt Seller" across on of his shoulders causing only a slight wound. ___[?] "Dirt Seller" continued to advance upon the guard who warned him to halt and unless he did he would shoot him in his face. So after a few moments hesitation, he submitted and was returned to his ell. Dirt Sellers wounds were carefully attended to and when he was executed was able to stand on his feet.

"Wilson" was sentenced to be hung at the same time with "Dirt Sellers" but had on the 26th of September 1877 had his sentence of death commuted to ten (10) years imprisonment by Executive Clemency.

Indian Journal, January 4, 1886
Capt. Sixkiller made a slick capture last week at Weber Falls. He was after Alf Rushing, alias Ed Brown, wanted for the killing of Jackson Bartfeld in 1877, also for the murder of the city marshal of Wortham, Freestone, County, Texas. He received information that Brown was working near the Falls and had been for several years. As the Captain and Bill Drew came near the place where Brown was staying, they gathered up a bunch of cattle, and driving them up, asked permission to put them in a yard there for the night. The request was granted, and Brown was called from the crib where he was at work to help pen them. While driving them Sam worked around to where Brown was, and throwing down on him, took him completely by surprise, and he could offer no resistance. The cattle were then turned loose. Brown denies he is the man wanted by the officers, but they are certain they have the right party, and he is being held here awaiting the Texas officers.

Indian Journal, June 11, 1885
Yesterday morning at Post Oak Grove, thirty miles west of this place, Captain Sam Sixkiller, with Policemen Laftore, Murray and Gooden, and C. M. McClellan, a prominent stockman of the Cherokee Nation, were in pursuit of a band of Negroes, headed by the notorious desperado, Dick Glass, who had been to Denison for a wagon load of whiskey and were on their way back to the Seminole Nation. The officers had with them a colored spy, to locate them.

After this was done, the officers left the main road and got around ahead of them and selected a place near the roadside to await their approach. About 7 o'clock the Negroes came along, one driving the wagon and Glass and two others following close behind. When within ten feet Captain Sixkiller stepped out into the road and commanded them to surrender. Instead of doing so they started to run. After Dick ran a few steps he succeeded in getting his pistol out, and he turned and fired on part of them. Dick Glass and Jim Johnson were killed. Some of the officers shot the driver, slightly wounding him. The officers thinking him dead pursued the remaining one and succeeded in capturing him after a race of a half a mile.

After returning to the place where the shooting began, they found the driver and the horse gone, the wagon having broken down. Two of the police started in pursuit of drive and horse, and after a race of six miles Policeman Laftore overtook him in the prairie. The Negro, seeing that he was about to be captured, made for a tree a short distance from the road, but the policeman was too quick for him and cut him off from the tree, and ordered him to surrender and throw down his gun. He saw the game was up and threw up his hands.
After returning with the prisoner to the scene of the first encounter, the bodies of Glass and Johnson and the two prisoners were put into a wagon and brought to Colbert, where Glass, was fully identified by a number of parties.

Indian Journal, June 11, 1885
Dick Glass Gone
He and a Companion Are Slowly Roasted
On Thursday night Capt. Sixkiller received a telegram from Policeman Robert Murray, of Colbert, stating that Dick Glass and three companions has passed through that place bound for Denison with several ponies to exchange for a load of whiskey and that he would return the next day.

Friday morning Capt. Sixkiller was on hand and he and Policeman Robert Murray, Frank Gooden, Leflore and C. M. McClellan, a well-known cattleman of the Cherokee Nation started out to Post Oak Grove to intercept them. They arrived about 10 o'clock at night and by means of a colored man located the parties about five miles south of Emit and thirty miles from Colbert When the moon arose about three o'clock Saturday morning they saddled up and getting near Glass's camp hid their horses and lay in the brush for them to appear.

About seven o'clock the outfit was discovered coming along the road. Richmond Carolina was driving and Jim Johnson, Dick Glass and Sam Carolina were walking behind the wagon, the forty gallons of whiskey they had proving as much as their tender shouldered ponies cared to pull. When within a few feet of them the officers stepping into the road, Sam Sixkiller in the lead, and ordered the Negroes to surrender. Instead of doing this they attempted to escape. Dick pulled his pistol and turned to shoot when a charge from Capt. Sixkiller's shotgun went into his breast and another into his head, killing him instantly. Jim Johnson also attempted to shoot but a dose of lead settled him.

In the meantime the driver had whipped up and as he was going by Leflore and McClellan ordered him to halt. As he did not they fired and he fell into the wagon apparently dead. Then they pursued Sam Carolina and after a half-mile chase succeeded in capturing him.

Returning they found that Richmond Carolina had only been slightly wounded and had unhitched and taken the horses and Dick's Winchester and escaped. Laflore and Gooden started after him but the latter's horse soon gave out and after a chase of five miles Laflore came alone and caught up with him. The darky made for a tree with the intention of resisting but was headed off and compelled to surrender.

The prisoners and the two bodies were then brought there and put in the cooler preparatory to being taken to Ft. Smith. The reward of $500 for Glass was "dead or alive" and Capt. Sixkiller will apply for it in a few days.

Indian Journal, December 29, 1886
A Terrible Tragedy
Capt. Sixkiller, While Unarmed Is Shot Down
On Our Streets
Thursday's and Friday's races here brought a miscellaneous crowd to our town, and the numerous Christmas bottles rapidly filled a good number of the crowd full to overflowing. So much drinking was going on that many would not go out to the grounds and everyone was confident that at least one tragedy would be enacted here during the holidays, but no one imagined that Muskogee was to loose a good citizen and the Territory one of the bravest of officers.

The chain of circumstance leading to the killing of Captain Sixkiller is as follows:
About 4 o'clock Friday afternoon Alf Cunningham, while drunk, "threw down" on Tom Kennard, a Creek Lighthorseman, in the door of the Commercial Hotel, but did not shoot, though a minute afterwards he would have done so had not Mrs. Renfro, who standing beside him, succeeded in getting his pistol. As he came down the steps of the hotel Kennard met him and dealt him a blow over the head with his six-shooter. This enraged Alf and he was determined on revenge. About 4:30 he found Dick Vann, his brother in-law, who was ready to help him in any emergency. Both were unarmed and went to Turner & Byrne's store purchase a pistol, but looking for trouble, C. W. Turner refused to sell him one. On failing there both went to the Mitchell House and finding the city marshal Shelly Keys there, before he suspected their intentions they had him down and disarmed and it is thought would have killed him there had it not been for the crowd, as he is under their displeasure. Finding Al Farmer's shotgun they took possession of it notwithstanding Farmer's remonstrance, and they were then armed and prepared for any deed.
Up to this time it is presumed they had not thought of Sixkiller, but as they came up the street half crazed with liquor they were ready for the first person against whom they had a grudge, and Tom Kennard in particular. At the steps leading down from Turner & Byrne's porch they met Capt. Sixkiller, who was entirely unarmed. To make sure of their man in the darkness one called "Sam!" and on hearing his name the Captain stepped towards them and about four feet from the corner of the porch. Dick was heard to say in the half crying voice he uses when mad "You'll never do that to me again," or words to that effect, when the shotgun in the hands of Alf was leveled at the Captain, who must have knocked it aside as the charge of fine shot it contained partly passed through his clothing and lodged in the gate of the lumber yard. At the same instant Dick, who was positively identified by an eyewitness, fired in rapid succession four shots into Sixkiller, who staggered and fell on his hands and knees on the steps, then to make sure of his work Vann fired another shot into the body. A few heavy groans and all was over, the deed was done. The two men then ran half leisurely down Main street, turned the corner and passed the billiard hall and on out of town. Saturday night it was reported they attempted to lodge with John Lowrey, who objected, and in flourishing a pistol Dick's weapon was discharged, the ball going across the base of his thumb.

Saturday morning writs, were sworn out before Commissioner Tufts and placed in the hands of Deputy U. S. Marshals Dalton, Tyson, Campbell and Hayes, and although they made a vigorous search until Sunday morning, and at one time were within a half-mile of Dick and his companion, they did not succeed in finding them.

Martin and Luke Sixkiller, brothers of Sam, Policemen Fields Laflore and Maj. Hodges were also here Saturday, but in the absence of orders did not join in the pursuit. On Monday evening Agent Owen returned from the Cherokee Nation, and at present writing is making preparations for an active hunt for them. Parties reported them in the thick bottoms of Gooseneck Bend, about ten miles east of town, the locality in which Vann did the scouting a couple of years ago when wanted for assault on Captain Hammer.The funeral of Captain Sixkiller took place Sunday morning at 11 o'clock from the M. E. church and was conducted by Cherokee lodge A. F. and A. M., of Tahlequah. The church could not contain the friends who gathered from nearly every part of the eastern portion of the Territory to attend the last rites.

Among those present from Tahlequah were Wm. Ballarn, Waite Foreman, J. L. Adair Sr., J. L. Adair, Jr., T. R. Sixkiller, J. L. Stapler, H. C. Barnes, D. W. Wilson and others; from Choteau were G. H. Lewis and Butler Bros.; from Eufaula, Chief Perryman and wife, Dr. Leo Bennett and wife, Sam Grayson, Charles Gibson, and Roley McIntosh; from Savanna, Dr. E. Poe Harris; from Ft. Gibson, F. H. Nash, Colonel Rogers, Tom French, Mr. Doty, Wm. P. Ross, George Saunders, Wm. Scot and Mr. Pick.

The procession, which followed the remains to the grave was one of the largest every gathered together in this section of the country.Captain Sixkiller was born in Going-Snake District, Cherokee Nation, in the year 1842, making him forty-four years of age at the time of this death. He was raised in the Cherokee Nation, educated at the old Baptist Mission, Mr. Evan Jones being his teacher. At the breaking out of the war his father joined the Northern army leaving Sam to take care of the property.

A number of his neighbors proceeding to join the Southern army took him with them, and he enlisted with them under General Waite, serving one year. At the end of that time he went to Fort Gibson and joined a Federal artillery company, of which his father Redbird Sixkiller, was first lieutenant. He was married at Gibson December 23, 1865, to Miss Fannie Foreman, and moved to Tahlequah, where he lived on a farm until he was appointed High Sheriff. After serving in that capacity for three years, while he and his deputies were attempting to arrest Jeter Thompson the latter was killed. For this he was tried and exonerated.

In 1879 he moved to this place on being made Captain of the U. S. Indian Police of the five tribes. About three yeas ago while trying to arrest a whiskey peddler near Eufaula the man resisted and was killed by the Captain and his brother Henry in self-defense; and also about a year and half ago he killed Dick Glass while attempting his capture. At the time of his murder he was U. S. Deputy Marshal, and was a valued member of the secret service of the Missouri Pacific.

The Captain has done probably more than any one person to free the railroad towns of this Territory of their dangerous and reckless elements, and to him the country owes in a great degree the comparative security to life and property that it now enjoys.

My research shows that Dick Vann was the most notorious Cherokee Freedmen during the 1880's in the Indian Territory. His notoriety would not be replaced in the Cherokee Nation until Crawford Goldsby aka Cherokee Bill would come along in the 1890s.

Winfield Courier, Thursday, March 11 1886
Rich Hill Mo.,March 6th. J. T. Pryor, formerly of Bates County, was arrested by Samuel Sixkiller, Captain of the United States Indian Police. The latter arrived here Thursday morning, looking for witnesses, which he found without trouble in the person of Mr. John Klons and his daughter, Mrs. Emma Pryor. James T. Pryor married the daughter of Mr. Klons about 3 years ago, but soon got tired of married life and decamped for parts unknown. Lately, he turned up in the Indian Territory as Charles Darling and married a half blood Cherokee Indian woman. When by some means it leaked out he was married already, Captain Sixkiller instituted an investigation whithe the above result. James T. is good for three years in the pen.