This Biography of John Arnold Callaway’s life was written by Rex Arnold Reynolds, son of Enid Callaway-Reynolds and grandson of John Arnold Callaway.
I grew up knowing my aunts and uncles, the children of John Callaway’s two families. In turn they grew up with John Callaway and they knew him well. They lived in the places described in this biography and relayed to me and my cousins much of the information that has been passed on in this biography. And, I was lucky to grow up with my cousins. Sometimes we even lived with each other. We recognized each other as members of an extended family and we grew up in northwest Oklahoma until we were adults and know the family places described here.
This biography is mostly for future generations of the John Callaway family. Most do not know each very well, if at all, and it is hard for them to have a sense of family with people they may never have met. It was written in the hope that it will give them an understanding and appreciation for those who came before them, and for each other, and for their place in a great American family. They are the beneficiaries of this family legacy of pioneer men and women and I would like for them to be able to embrace it with the pride that flows from knowledge of the character, accomplishments, and contributions of their predecessors.
The information in this Biography comes from a variety of sources. Some of it comes from historical records and documents, genealogical records, and written correspondence. Some of this information is anecdotal and has been passed down to family members by John’s children or other family members. I cannot attest to the accuracy of all of it; but, I have endeavored to include only that which is most credible and omit that which I believe is suspect or identify it as such.
In addition to enumerating the facts of his life, I have tried to place it in the historical context of the time in which he lived in the hope of better understanding the person he was and the life he lived.
I have also added maps and other geographical information to assist the reader in locating places and understanding their relationship to each other. I hope the pictures that have been included will add additional substance to the people and places.
In any case, I believe this biography describes and portrays the essence of the life of my grandfather, John Arnold Callaway.

Rex A. Reynolds
December, 2013
Revised: March, 2015
eMail: [email protected]





I would like to acknowledge and thank all those who contributed family information and pictures which made this endeavor possible, especially Pat Callaway-Maskus, the daughter of Fred Callaway who wrote down many of her father’s memories and compiled a family album.
Thanks to my mother, Enid (Callaway) Reynolds, and to all of my aunts and uncles and their spouses who were special to me and who shared their memories of their father over the years. And, a special thanks to Arnold Callaway, the last living child of John and Minnie Callaway, for his contribution of information, memories, and pictures.
For all of my cousins, the children of John Callaway’s children, who have passed down information about their grandfather that was related to them by their parents: Thank You. You all share in this biography, the story of your grandfather’s life.
A special thanks to my cousin Mona Lou (Callaway) Tea for additional information she provided which I have used in this revised version.
Finally, thanks to Samuel W. Newman, the grandson of W. T. “Bill” Callaway for information he has documented in his family history: From England to Texas 1640 – 1990. And thank you to all of you who read early versions of this manuscript and made suggestions, corrections, and editing comments. Your contribution has been invaluable.


John Arnold Callaway was a cowboy. He was born November 15, 1857 near Crockett, Texas, in Houston County, the fifth of nine children born to James Wilson Callaway from Franklin County, Georgia and his wife Caroline Elizabeth Dillard from Williamson County, Tennessee. He was the seventh generation in the pioneer family of Peter Callaway, his 4th Great Grandfather, who came to America from England in, or before, 1640.
In the Texas War for Independence, Sam Houston had defeated Santa Ana’s troops in 1836, but they were not the bulk of the Mexican Army and hostilities continued periodically between Houston’s Texas troops and Mexican troops until a formal armistice was reached between the Mexican Government and the new Texas Republic in 1843 ending the Texas War for Independence.
John’s father, James, came from Georgia to Colorado County, Texas, west of present day Houston, in 1839. Shortly after he arrived, James was taken prisoner by elements of the Mexican army and held in captivity where he was mistreated. After a period of time, James managed to escape from the Mexicans, and although he had lost most of his clothes and was almost naked, he managed to find his way to Sam Houston’s Texas army and safety.
In 1835, John’s mother, Elizabeth Dillard, came from Tennessee to Houston County, in east Texas, with her family, and in about 1844, after the armistice with Mexico, James moved on to Houston County. After arriving in Houston County, James met Elizabeth and they were married on July 14, 1846; the year that the Mexican-American War (1846-1848) began in Texas.
After their marriage, James partnered with his father-in-law, William Dillard, and together they operated a large estate in Houston County, Texas. After 14 years, in 1860, William Dillard died and James was appointed executor of his estate. He had to sell the land and distribute the proceeds to the estate’s beneficiaries. This proved a costly chore for James, who had to post a $10,000 bond, a very large amount for the time, and in the process of administering the estate he lost a considerable amount of money.
Meanwhile, the Confederacy requisitioned the cattle and other livestock of the estate and paid for them with Confederate money which was worthless after the war. After his father’s death, John’s mother told him that his father, James, came into the house with a trunk full of Confederate money and in a rage began throwing hands-full of bills into the fireplace. When flaming bills began to fly out of the fireplace, she said that she was fearful that he would burn down the house and she begged him to stop. After James’ death, the family found the trunk filled with the remaining bills.
John Callaway was four years old when America was plunged into a Civil War (1861-1865) which, in addition to the death of his maternal grandfather the year before bankrupted his family. So, with no estate or land, few livestock, and little money remaining, James Callaway moved the family west to Gonzales County and then, in 1865 or 1866, on to De Witt County, Texas.
John spent his childhood, and attended school, in De Witt County through at least the sixth grade. He was literate, he could read and write, although his spelling sometimes left something to be desired, and he was good at arithmetic. For a cowboy living on the western frontier he was relatively well educated. He was a lifelong proponent of education. And, although he thought that boys did not require schooling past the eighth grade, he saw to it that his children received the best education that he could provide for them. In fact, two of his girls, Minnie and Nellie, went to college and became school teachers and his youngest daughter, Enid, went to nursing school.
In 1867 Joseph G. McCoy, built market facilities adjacent to a railroad siding at Abilene, Kansas and the great cattle drives began from Texas across the Indian Nations’ western Oklahoma Territory to Kansas.
John’s older brother William Theodore “Bill” Callaway went into the cattle trailing business in 1870, and Bill brought his brother David and thirteen-year-old John into the business to work as a drover and later as a trail boss. He also brought their younger brother George into the business a few years later. John spent the next thirteen years of his life driving cattle north from Texas over the Chisholm Trail to Abilene and then the Great Western Cattle Trail to Dodge City, Kansas and as far north as the Dakota Territory. Although there is no way to verify it, it was related by his sons, James and Fred, that their dad had worked for South Dakota cattle baron, Murdo MacKenzie, as trail boss for a couple of trips up the trail to northern locations in the late 1880’s or early 1890’s.
The four brothers, Bill, David, John, and George Callaway made many of their trips up the cattle trails together. When they decided to settle down, John’s Brother Bill remained in Texas and became a deputy sheriff in De Witt County. But, rather than return to Texas, John decided to stay in Kansas and Oklahoma. George returned to Texas for a while: but, after a few years he joined John in Oklahoma. David left the family business and the family lost track of him about 1875.
John’s father James had come to Texas from Georgia and he and John’s older brother Bill were more southern in their outlook than John who was essentially a westerner and race and color mattered little to him. He told his son John William that he did not want to return to Texas to settle down because he was offended by the treatment of black and Mexican cowboys there.
Among other things, it offended his sense of fairness that they could not eat at the same table with the white cowboys when they were working on the ranches in Texas. John reasoned that they did the same work as he and the other hands and he felt that they deserved to be treated the same as the white cowboys, just as they were when they were on the trail.
At Pioneer Hall in San Antonio, Texas, the names and pictures of many of the early Texas trail drivers have been recorded for posterity. John’s older brother, W. T. “Bill” Callaway, is one of those cowboys whose name is there. Some of the men whose names are recorded there, like Jesse Chisholm, and Charley Goodnight, are legendary; but, most are men whose lives are lost to history. Following are the names of eleven of these stalwart men along with that of Bill Callaway:

Cade, James G.	Gardner, J. W.
Cade, J. J.	Gardner, Sam
Callan, Jim	Gates, James H.
Callaway (Bill) W. T.	Gibson, James
Castlebury, R. L.	Goodnight, Charley
Chisholm, Jesse	Gray, W. H.

John Callaway’s family had given him a solid foundation to build on; but, to understand and appreciate how he had became the man he was when he reached adulthood, it is equally important to understand the events and forces that shaped his teenage life: the land, the inhabitants of the land and their struggles, the work, the animals, the violence of this time on the Great Plains, and his experiences in this environment. It was an era of profound change in the American west and a time of profound change in John’s life as he became a man.
The Indian Nations were comprised of Indian Territory on the eastern side of the Cross Timbers and Oklahoma Territory to the west. The Cross Timbers was a thick, almost impenetrable, primeval forest of hardwood trees, mostly blackjack and post oak, which bisected what, would become the State of Oklahoma diagonally into two almost equal parts. It ran from southeastern Kansas through central Oklahoma down into west central Texas ending near Waco and the Brazos River. The main part of this forest was from ten to thirty five miles wide with fingers branching out periodically to the east and west forming a boundary between the forest and prairie lands to the east and the Great American Plains to the west.
Indian Territory, east of the Cross Timbers, was occupied by Indians that had been resettled there from other sections of the country, including the Cherokee, Choctaw, Chickasaw, Creek, and Seminole, the so-called Five Civilized Tribes, from the southeastern U.S. Oklahoma Territory to the west was the traditional territory of the Plains Indian tribes: the Comanche, Kiowa, Cheyenne, Wichita, Caddo, Ponca, Osage, and others that were still actively hostile to the United States and white settlers in the second half of the nineteenth century. It was in the west, in Oklahoma Territory, where the more hostile plains tribes lived, that the major cattle trails were located and the historic cattle drives took place.


It is crucial to understand that long before the Europeans came, the Great American Plains had been a battle ground. For centuries the Indian tribes were mortal enemies and battled each other for territory and survival. Now they stood defiantly and resolutely against the overwhelming forces of white civilization. For the native people it was a struggle to retain their lands and their way of life and they would prove formidable foes. The last 50 years of the nineteenth century was the era of the great Indian Wars. It was the culmination of two centuries of conflict between Indian peoples and the white newcomers and it would frequently be violent and bloody and John Callaway lived and worked in the midst of this battle ground.
For years the southern plains Indians, the Comanche, Kiowa, Southern Cheyenne, and others, had been on the war path, mostly in Texas and Oklahoma Territory. They raided New Mexico, southern Texas, and northern Mexico for live stock and slaves several times a year, and they waged war against whites and Mexicans wherever they found them. And, in 1874, they attacked heavily armed buffalo hunters at the battle of Adobe Walls in the Texas panhandle. To combat these Indian depredations the Texans formed Ranging Companies, called Texas Rangers, and the U.S. sent cavalry and infantry units into Oklahoma and Texas.
In the multi-year Red River War with the U.S. military they went unconquered until the winter of 1874–1875 when they were defeated by Ranald MacKinzie, and the Fourth U.S. Cavalry in Palo Duro Canyon in the Texas panhandle, leading to the surrender of the Comanche war leader, Quanah Parker, and his warriors that summer at Fort Sill, Oklahoma Territory. Quanah Parker was himself, the son of the Comanche Chief, Peta Nacona, and a white woman named Cynthia Ann Parker, who had been captured as a nine year old girl in a Comanche raid in east Texas in 1836. He added his mother’s surname, Parker, to his name as a tribute to his mother and to recognize his white heritage.
General Philip Sheridan, in command of the U.S. Army's Department of the Missouri in 1868, decided to send George Armstrong Custer and the U.S. Cavalry into Oklahoma Territory for a winter campaign to pacify the remaining hostile Indian tribes.
During the winter campaign of 1868, Custer massacred Black Kettle, a Cheyenne peace chief, and his village of Sothern Cheyenne who were encamped on the Washita River in western Oklahoma Territory for the winter. At the time of Custer’s attack, the warriors were gone on a hunting trip and the village was occupied mostly by women and children and their massacre would enrage the plains Indians. A story has been told that sometime later in a pow-wow, Cheyenne Chief Medicine Arrows (aka: Stone Forehead) insulted Custer by emptying the pipe’s ashes on Custer’s boots. He then rebuked him for the massacre of Black Kettle’s village and predicted Custer’s downfall.
Farther north, in Montana, in The Great Sioux War of 1876, Sitting Bull and Crazy Horse leading Sioux and Cheyenne warriors defeated General George Crook at the Battle of the Rosebud and then they defeated the Seventh U.S. Cavalry and killed George Armstrong Custer in the battle of the Little Big Horn, fulfilling Chief Medicine Arrows’ prophecy of Custer’s downfall. When the Sioux and Northern Cheyenne were finally subdued the Sioux were moved to reservations in Nebraska and Dakota Territory and Cheyenne leaders Dull Knife and Little Wolf with their Northern Cheyenne were relocated to Cheyenne-Arapaho lands in central Oklahoma Territory at the Darlington Agency adjacent to Fort Reno (now El Reno) Oklahoma.
In Arizona, New Mexico, and Texas the Apache wars continued non-stop from 1849 until 1886, with the U.S. Army and Kit Carson defeating the Navajo in the battle of Canyon de Chelly, then subsequently defeating war leaders Mangas Coloradas, Cochise, and Victorio, from other Apache tribes. At the end, General Crook and General Miles with the U.S. Cavalry finally made life so impossible for Geronimo and his band of Chiricahua Apache that they surrendered and were relocated to Florida and later to Oklahoma Territory, essentially ending the Apache wars.
In Oklahoma Territory in 1878, Dull Knife and Little Wolf led the Northern Cheyenne across northwestern Oklahoma Territory and western Kansas in a breakout and exodus from the Darlington Indian Agency near Fort Reno, fleeing the southern Cheyenne lands in central Oklahoma Territory to go back to the Wind River country of Wyoming. Along the way Black Coyote and his Cheyenne dog soldiers killed a number of settlers and cowboys, three of whom were Quinlan ranch hands in Clark County Kansas where John Callaway worked after quitting the trail.
The West was aflame with war between the native peoples and the white European newcomers.
The Indian Nations were also infamous for attracting lawless men trying to avoid the consequences of their lawless life style. The Indian Territories were a haven for bank and train robbers, cattle rustlers, horse thieves, and murderers. Some of the more well know outlaw gangs escaping to the Indian Nations were the James gang, the Doolin gang, the Dalton gang, the Younger gang, and the black and Indian gang of Rufus Buck. They were also the home of renegade Indian outlaws and serial killers, such as, Cherokee Bill and Bluford ‘Blue’ Duck.
And, in addition to the inherent dangers of working with wild livestock, fording rivers, traversing dangerous terrain, and spending large amounts of time in areas sometimes occupied by hostile Indians or outlaw gangs, John Callaway was also forced by necessity to associate with men who were intemperate and not of the highest character. Some of them were, or would later become, outlaws. The Doolins, the Daltons, and Sam Bass are some of those he knew and with whom he had at times worked.
Oklahoma with its inhabitants was a wild, hostile, rugged, demanding, and unforgiving land; but, John learned early that danger wasn’t just confined to the trail and the Indian Nations. Once, while still a teenager, he found himself in the wrong place at the wrong time. His outfit arrived outside of Dodge City, Kansas with their herd and they were low on supplies. So, as the youngest and lowest ranking man, John was sent into town with a wagon to bring back the needed supplies. But, before he could accomplish his task he found himself caught between two groups of men approaching each other from opposite ends of the street with pistols, rifles, and shotguns intent on confronting each other. To get out of the way young John escaped up an alley between two buildings where he could wait it out. During the confrontation a group of men came up the alley and discovered him. He escaped harm because the man who spotted him told the others to move on, that he was just a kid. He had been lucky.
In another incident, as a young man, while riding in the wilds of west Texas, John had come upon a cowboy who was in the process of branding calves. As John rode up the cowboy was attempting to rope one of the calves without much success. Young John was very good with a rope and eager to show off his skill, so he offered to rope the calf for him. The man gratefully accepted his offer and John quickly roped and tied the calf. As the man was applying the brand a rancher with a group of cowboys rode up with guns drawn and confronted the two of them. It turned out that the cowboy who was branding the calves was a thief who had rounded-up and was applying his own brand to calves that belonged to the rancher. At this point, John quickly realized that he was in real trouble. Fortunately for him, after a few minutes of explanation and telling them his story, the rancher and his men agreed that it was an honest mistake on his part and let John continue on his way. Again, he had been lucky.
In conversations with John’s sons, they marvelled that their father seemingly was able to survive so many dangerous situations, no matter the gravity of the circumstances, and expressed their amazement at their father’s ingenuity, his depth of knowledge and his wisdom. Several of them related the above incident as one example.
When John related incidents to his sons, he made it clear that the close calls he experienced were deeply imprinted in his memory and that they should be considered lessons. These incidents, where his survival was on the line, taught him the importance of heightened awareness, and quick and critical thinking; and, that things are not always what they appear to be.
In this incident, one would assume that upon reflection, he realized that it was highly unusual for one man alone to be branding cattle in an isolated location and that it should have aroused his suspicion. He may well have had a premonition that something was not quite right as he had ridden up; but, had dismissed it without giving it the attention that it obviously deserved. So, the lesson to be learned was, if something did not seem quite right, there was a good chance that it wasn’t and healthy suspicion was a good thing; moreover, heightened awareness, critical thinking, situational analysis, attention to feelings of uneasiness, and caution were important and should not be dismissed lightly; since, they might save your life.
When John Callaway was a young man, it was a difficult and dangerous time to live and work any place on the western frontier; but, it was especially dangerous on the southern plains in Texas, Kansas, and in Oklahoma Territory where he lived out his life. He obviously learned his lessons well, because he avoided making the same mistake twice, and in the era in which he lived, you could not always count on being lucky, you needed to be smart to survive, and John lived to be an old man.


As a cowboy and a frontiersman, John Callaway lived his early life on the edge of the great American western frontier herding wild Texas cattle north to the railroads in Kansas and beyond. Most of the time, during these years on the trail, his home was in a saddle, on horseback, under the sun and stars in Oklahoma Territory, good weather and bad. He became a tough man who did tough, difficult, and often dangerous work in a sometimes violent environment. And, because it was the era of the great Indian wars on the western frontier, herding wild longhorn cattle across Oklahoma Territory was doubly dangerous.
John Callaway was not a large man. He was about 5 feet, 10 inches tall and weighed about 170 pounds; but, by all accounts he was extremely strong with great endurance gained through years of hard work. During the course of his life he sustained many injuries and broken bones. He was an exceptional horseman and skilled at managing both cattle and men. And, like many western pioneers, he was good at building things and able to fix most machinery when it broke down; skills that he passed on to his sons. In fact, under John’s tutelage, all of his sons became highly skilled ranch hands with a strong work ethic.
In the west your good name was a reflection of your reputation and your reputation had to be earned. A man’s reputation was determined by his actions and John’s actions had earned him a sterling reputation. He was a principled man who lived by his principles, and those who knew him said that he was a man of character and honor whose word was his bond.
John liked people and treated everyone with respect unless they showed themselves unworthy of that respect. He was friendly and considerate with a sense of humor, and although he was quiet, he was not withdrawn, and most people liked him and enjoyed their low key conversations with him. Generally, men felt a sense of camaraderie with him and women found him charming. He was a charitable man who was quick to help those in need. And even with the inherent difficulties of working with large and sometimes temperamental animals, he would not tolerate their mistreatment. And, although John was generally easy going, he had a temper, which he managed to control most of the time; but, he was a very tough man and it was generally unwise to provoke him.
John Callaway was a privately religious man. Most of his life he was not in close proximity to a church and only found his way to church services infrequently; however, he held his Christian beliefs firmly and attempted to live his life in harmony with those beliefs and the Christian moral and ethical code. On the occasion when a minister was in the area, he would extend them an invitation to enjoy the hospitality of his home and share their message with his family.
His principal vices were swearing and loss of temper, both of which he considered failings. He did not play cards and he did not drink. The family would keep alcohol in the home only for medicinal purposes. John told his sons that he had seen more men killed as a result of disputes over card games and excessive alcohol consumption than for any other reasons and he implored them not to fall prey to these temptations. But, John loved to have fun, he loved music, and he loved to dance. He taught his girls to dance and, whenever possible, the family would take advantage of opportunities to attend dances.
John spent his teenage years trailing cattle. He grew into adulthood and become a man traveling the great cattle trails through Texas, Oklahoma, Kansas, and the northern territories. He learned the geography and become acquainted with the inhabitants and wildlife, and along with the cowboys, cattle, and horses they were his world.
The Chisholm Trail ran to the west of, and roughly parallel to, the Cross Timbers through Oklahoma Territory generally following the ninety-eighth meridian. The trail began at Fort Worth, Texas, although herds might join it at any point south of the Red River. It crossed the river at Red River Station southeast of the modern day town of Duncan, Oklahoma and progressed north passing by what became the communities of Comanche, Apache, Duncan, Rush Springs and Chickasha where a split developed. The western split passed Fort Reno, which later became the town of El Reno, and the eastern split passed Yukon, Oklahoma before the two merged at Kingfisher prior to crossing the Cimarron River at the Dover Stage Crossing. It continued on past what became the communities of Enid, Pond Creek, and Medford before moving into Kansas on the way to Wichita and Abilene, a total distance of about 500 miles. Current Highway 81 from Fort Worth, Texas through Oklahoma to Wichita Kansas generally follows the route of the Chisholm Trail.
The Great western cattle trail ran west of the Chisholm Trail. Bandera, Texas, west of San Antonio, was considered its earliest origination point and it headed north passing what became the cities of Brownwood, Abilene, and Vernon, Texas before crossing the Red River at Doan’s crossing southeast of Altus, Oklahoma. The trail ran almost parallel to the Oklahoma-Texas border moving north past Elk City, through Comargo, east of the Antelope Hills, and moved on north to the west of Vici. At this point, the trail veered to the northwest passing Fargo, southwest of Woodward, where it began to run parallel to the military road and proceeded north passing a few miles to the west of Camp Supply, now Fort Supply. From there it continued on northwest past the border through the big basin area to Dodge City, Kansas. The entire length of the trail was about 600 miles from Bandera to Dodge City with herds joining the trail at different points before the Red River.
A typical cattle drive lasted from 110 to 150 days, depending on where the herd originated and how long it took to round-up and gather the cattle. Usually, cattle were only moved ten or twelve miles a day so they would not lose an excessive amount of weight during the trip. Drives to northern locations took even longer.
Cowboys were paid 75 cents to a dollar a day, $20 to $30 dollars a month, with room and board furnished. A good pair of boots cost $20, a hat $10, and a saddle $40 to $60. A saddle horse cost $10 to $30, depending on how well it was trained and how much experience and skill it had working cattle; however, most outfits rounded up wild horses and broke and trained them themselves, sometimes creating a herd of several hundred saddle-broken horses, called a remuda, from which cowhands chose their mounts for the day. Cowboys furnished their own tack and the trail outfit included wranglers for the remuda and furnished a string of horses for each cowboy.
The business of cattle trailing was not an easy life. Personal accommodations were non-existent. The men slept in their clothes on the ground. They might go for weeks without a bath or a change of clean clothes. The cook would usually provide a tub of water for the men to wash-up before meals, which consisted mostly of the basics: biscuits or cornbread, sometimes with meat and beans, sometimes with stew, or maybe chili. And, occasionally, they might get a treat like pie or cobbler when fresh fruit could be acquired.
After the civil war the longhorn cattle in Texas were mostly wild open range cattle that were often difficult to handle and could be dangerous. On the trail there were many river crossings to be made and sometimes difficult terrain to traverse which regularly resulted in injuries to cowboys and John Callaway was no exception. Mostly, the weather was hot and the trail was dusty with occasional summer storms producing lightning and thunder that could spook the herd and cause out-of-control stampedes.
Because Oklahoma Territory was the domain of outlaws and hostile Indians, preventing the herd and remuda from being stolen was a continuous problem. They usually gave the local tribes a few head of beef as consideration for crossing their land. And, when hostile Indians were close, they frequently let them take a few head of cattle rather than stop them and risk a deadly confrontation. Horses were not given-up so easily and horse thieves and cattle rustlers were given no quarter. The ownership of firearms and the ability to use them proficiently was a requirement for cowboys. And John’s sons recalled that their father was an expert shot with a rifle.
Sometimes the problems cowboys faced on the trail were man-made. Some men thrived on conflict and sometimes made life difficult for others. In one instance on an early cattle drive, they came to a river crossing to find that it had been blocked. A man appeared out of a small shack and informed the trail boss, John’s brother, Bill Callaway, that it would cost fifty cents a head for the herd to cross the river. As Bill contemplated what to do, one of his men rode up and made Bill a proposal. The man had been a teamster and was an expert with a bull whip. He said that for fifty cents he would cut the man’s clothes off with the whip and teach him a lesson. Bill reached into his pocket and flipped his cowboy-teamster fifty cents. The ex-teamster uncoiled his bull whip and after a few strokes of the whip, the man raced for his shack, jumped on his horse and rode away welted and bloody with his shirt ripped in several places by the whip. The extortion attempt failed and the drovers proceeded to move the herd across the river without issue.
In 1883 at the age of 26, after thirteen years of trailing cattle, John was a highly skilled cowhand; but, although he was still a young man, he was worn down and ready to leave the trail. What John Callaway knew was horses and cattle, so he went to work on one of the large cattle ranches that had developed in western Kansas during this period.


For eleven years after he left the cattle trailing business, from 1883 until 1894, John mostly worked on ranches in Texas, Kansas, and Oklahoma Territory; although, he did on occasion work as a trail boss for a few drives during this period. He worked at one time or another on the Quinlan Brothers cattle operation in the Cherokee Outlet in Oklahoma Territory, the famous XIT ranch in the Texas panhandle, the Claremont Land and Irrigation Company, the Quinlan Brothers Ranch, and the C. D. Perry Ranch in Kansas.
The Quinlan brothers, William, Thomas, and Robert, operated a ranch in Clark County, Kansas, just a few miles north of the Cherokee Strip. As members of the Cherokee Strip Cattlemen’s Association, they had leased grazing land from the Cherokees in the Cherokee Outlet west of the Cimarron River, on land that became Woodward County after Oklahoma statehood, and they hired John Callaway as foreman for this operation. John worked for the Quinlan brothers in Oklahoma Territory through the disastrous winter of 1886-1887, which killed many head of cattle, badly depleting the herds, until 1890 when the U.S. Government invalidated the Cattlemen’s Association lease with the Cherokees and forced the cattlemen to move their herds off of Cherokee land and out of the outlet. Later, the Quinlan brothers would return to the Outlet after it was opened for settlement and build a big new ranch.
Matilda Crupper was born September 07, 1857 in Quincy, Adams County, Illinois, where she met her first husband Thomas C. Douglas. They moved west to Camp Supply in Oklahoma Territory where her first two children, Jennie A. and Lucy T. Douglas were born. Jennie was born in December of 1886 and Lucy was born in January of 1889.
Tom Douglas was a teamster and traveled between the settlements along the western cattle trail delivering supplies. He had chosen the community around Camp Supply in northwest Oklahoma Territory for his home base because it was a convenient location for his travel needs and because it was adjacent to an Army post and he believed it would provide a safe place for his family while he traveled.
John frequently moved cattle between the Quinlan ranches in Kansas and Oklahoma Territory using the Chimney Creek cattle trail to Camp Supply. Camp Supply was a convenient stopover for him and he was already familiar with it because during his cattle trailing days they had often stopped close by with their herds to give them some time to graze for a few days and gain weight before continuing on to Dodge City, Kansas. It also gave the cowboys a break with a chance for some downtime in town, such as it was.
It was during these trips with stops at Camp Supply that he met the Douglas family. John loved children and would often spend some time talking, joking, and laughing with the local kids when he came into town. The Douglas girls were among that group of local kids and over time he developed a friendship with them. Eventually he met their mother Matilda, called “Tillie”, and they also became friends. John already knew Tom Douglas and he had also come to know Tom’s family.


Tom Douglas was a serious alcoholic and was seldom at home and when he was it was often not a pleasant time. John Callaway was a very different man than Tom Douglas. He didn’t drink and he was pleasant and easy to be with. So it happened, over time, during his stopovers at Camp Supply, that John and Matilda developed feelings for one another. She wanted to divorce Tom and build a new life with John; but, John would have none of it.
Whatever his feelings for her, or however much he liked the children, because she was a married woman his personal ethics would not permit him to act on those feelings; so, they made do with being friends.
In 1890 Tom Douglas passed away and Matilda buried him in Woodward, Oklahoma Territory, a few miles south of Camp Supply. After the funeral she caught the train with her two daughters and they rode it east where it stopped to let them off at the siding for the Quinlan Brothers cattle loading pens. A small community had sprung-up next to the loading pens which had a livery stable where she rented a buggy and horse. She then drove to the Quinlan ranch headquarters where ranch hand Perry Phillips would latter recall going to find John Callaway to tell him there was a woman with two little girls who were there to see him.
As an old man Perry Phillips frequently spent his afternoons at the Woodward town square. On Saturdays, John’s son, John William Callaway, would load his family in a wagon and they would go to town for supplies. Horses and wagons were parked on one end of the town square and it was a gathering place for people to catch-up on the local news and gossip. On these Saturday afternoons Perry would often sit with John William’s young daughter, Mona Lou, telling her stories and reminiscing about old times. He had known and worked with her grandfather, John, for years at the Quinlan ranch and he told her stories about him and often recounted for her the time that her grandmother, Tillie, came to the Quinlan ranch with her two little girls to see her grandfather, John.


Matilda Ann “Tillie” Crupper-Douglas was a widowed woman with two daughters and she was now free to pursue a new life with John Callaway. Because he worked on a large isolated ranch not suitable for family living, John secured a position for Tillie as a cook at the Cattle King Hotel in Dodge City, Kansas until he could make arrangements for them to get married and become a family. Matilda was pregnant with her third child when Tom died and Flora Mae Douglas was born in April of 1891 in Clark County Kansas. In the meantime, John had taken a job at the Claremont Land and Irrigation Company Ranch in Kansas to be close to Tillie and the girls.
At the age of 35, John married Tillie on August 16, 1892 in Englewood, Clark County, Kansas. Because he had lived and worked in the outlet prior to it being opened for settlement in 1893, John was not eligible to make the run and stake a homestead claim until later, after the opening; but, having worked for the Quinlan brothers in the Cherokee Outlet he was familiar with the land near the Cimarron River and thought that it would be a good area in which to settle.
In 1894 John brought his new family to Oklahoma Territory where they set up camp on Dog Creek on the east side of the Cimarron, just west of Waynoka, in what became Woods County, Oklahoma, in 1907 upon the granting of statehood. Tillie was pregnant with his son John William and the camp on Dog Creek was close to town. She and the girls lived there in two tents, one for cooking and one for sleeping, while John looked for a place to homestead and worked to build the family a permanent home.


Chimney Creek, a tributary of the Cimarron, was marked in those years by a gypsum and red sandstone column named Chimney Rock near its mouth. It is located in a remote area about twelve miles northwest of Waynoka on the west side of the Cimarron River in what became Woodward County after statehood. The creek flows northeast into the Cimarron through a canyon flanked by trees, good grass for cattle, and soil that is suitable for farming. And, the creek was a reliable source of water in all but the driest times. During the time he worked in the Cherokee Outlet, a cattle trail ran along the creek and John was familiar with the area. He had traveled it often before settlement and he could not get Chimney Creek and the little valley out of his mind.
In 1894 John staked his homestead claim on Chimney Creek where he built a one room cedar log house. When it was ready, he moved his family from their tents on Dog Creek into their new home there. He had constantly been on the move for 22 years and now he had a family and a place to call home. While he farmed and ranched his own place, he periodically worked on other ranches to make ends meet. He worked often for the Quinlan brothers who had purchased and leased land and operated a large new ranch headquartered a couple of miles southwest of his place. Over the years, he improved his home by adding a room connected by a hallway and he and his family lived on their Chimney Creek ranch for the next 17 years.


The land John had chosen for his home was some of the most remote and rugged land in the Oklahoma Territory. To the west of the Cimarron River’s south bank, (the river runs north to south here) from the north at Freedom, Oklahoma to its eastern bend south of Waynoka, Oklahoma the erosion which formed the Cimarron valley had created a steep escarpment with a plateau topped by gypsum cap rock to the west. On the low plain between the river and the plateau are a series of flat top buttes and mesas with valleys between them that open eastward toward the river.
The many buttes and mesas in the Cimarron valley plain are also capped with gypsum rock formations and their steep eroded sides often display horizontal layers of red sandstone, red clay, and white gypsum. Many of the valleys they form are watered with spring fed creeks and have an overlay of sandy loam that supports rich grasslands interspersed with trees, mostly cedar and mesquite. It was the valley watered by the spring fed Chimney Creek that John chose for his home.


On the western plateau behind the escarpment, the ruggedness of the land continues. Known as the Ragged Hills, the landscape consists of a series of sometimes rolling and sometimes steep sided hills interspersed with large rolling plains that extend west for twenty or more miles.
In places, the land is cut by long, steep ravines that can run for miles and in other places depressions will sometimes contain spring fed watering holes. The area is covered with well watered grass lands that provide excellent forage for cattle. Much of this land went unsettled for years after the opening of the Cherokee Outlet and about 30,000 acres of it was leased from the government by the Quinlan Brothers Cattle Company for their ranching operation where John frequently worked as a cowboy and range rider.


Because of the ruggedness and remoteness of the area, outlaws often traveled through it, and sometimes hid out in the remote ravines or canyons, usually, but not always, being careful to avoid the local population. The following incident demonstrates local residents concern about outlaws in the area. John was returning home during a severe thunder storm after a day at the Quinlan Ranch and he found himself having a difficult time finding his ranch in the darkness and rain. He assumed that he would be able to see the lights of the house to guide him, but there were none to see. He was finally able to get his bearings by sighting landmarks during lightning flashes and when he got to the house he was angry and barely in control of his temper. However, he soon relented and cooled down when Tillie told him that she was afraid to light lanterns because she was frightened and afraid that outlaws passing by would see the lights and come to the house seeking shelter.
The Atchison, Topeka & Santa Fe Railroad (AT&SF) built tracks through this area in the 1880s and the Quinlan brothers built cattle loading pens next to a railroad siding to support their cattle operation. In addition to the Quinlan brothers, other cattlemen often used the loading pens and a flourishing community had taken root there, and with settlement of the Cherokee Outlet in high gear, the town of Quinlan was founded adjacent to the cattle loading pens in 1901, in what became Woodward County, Oklahoma after statehood in 1907.
In their home in this rugged land, John and Tillie prospered and during their life together three children were born to them: Mary Ann Callaway, born July 28, 1893, in Englewood, Clark County, Kansas; John William Callaway, born April 15, 1895, in Waynoka, Woods County, Oklahoma, while the family was living on Dog Creek; and Caroline Elizabeth Callaway was born November 29, 1896, in their home on Chimney Creek in Woodward County, Oklahoma. With his three step-daughters, Jennie, Lucy, and Flora Douglas, John was blessed with a family of six children.
Sometime after John and Tillie moved to Chimney Creek, John’s younger brother George Dickerson Callaway moved his family from Gonzales County, Texas to the area nearby to be close to John. His place was west of the Cimarron and south of Belva in Woodward County, Oklahoma; and, on January 1, 1902, George’s last child, George Dickerson Callaway, Jr., was born there.
John’s life with Tillie and their family was satisfying and happy. The land was productive and the cattle business provided a decent living. He was doing well, he loved his family and his home, and he loved the land. He was content with his life and with the world. Time passed and for nine years, each year merged seamlessly into the next; but, the tranquillity of his life would not last.



1903 was an important year in the life of John Callaway. On May 28, his beloved wife Tillie passed away and was buried in the Waynoka Cemetery. John was devastated; but, he steeled himself against his grief and assumed the stoic demeanor he displayed all his life. On the frontier in the 1800’s the cycle of life played out often and death was not a stranger, it was a constant companion, and people seldom lived into old age. Extended grief was a luxury few could afford, because the process of maintaining life had to take precedence.
John was alone with his children, he missed his beloved wife and companion, and in his loneliness he felt the weight of his responsibilities more heavily than ever before. Life was hard; it was a day-light until dark affair filled with unending work. There were children to raise, livestock to care for, land to till, and crops to harvest. His only reprieve was that his older step-children were able to assume the domestic work for the family and care for the younger children while John did the ranch work.
In September that year, as a member of the local Chimney Creek School Board, John assisted in hiring 30 year old Minnie Gorman as the teacher for the local school. Because he was a widower with six children in school, John and Minnie became well acquainted during the course of the year.
Minnie Gertrude Gorman was born February 13, 1873 in Fithian, Vermilion County, Illinois, one of four girls and one son born to John Brooks Gorman and America Jane Norton. In about 1899 or 1900, her father loaded the family into a covered wagon and moved them west to Indian Territory where they stayed with a relative in Newkirk, Kay County, Oklahoma until John Gorman found land for a home. He found the place he wanted and brought the family to Heman, Oklahoma Territory, west of the Cimarron River on March 5, 1901. After they arrived at Heman, Minnie and her sister, Nellie Gorman, went to live in Alva, Oklahoma Territory, so they could attend school to obtain teaching certificates for the lower eight grades.
John Callaway married his second wife, Minnie Gorman, on September 29, 1904 in Alva, Woods County, Oklahoma Territory. John was 47 and Minnie was 31 years of age when they married. After their marriage, Minnie moved into the home on Chimney Creek to help John raise his six children.
John and Minnie lived in the home on Chimney Creek for seven years and three of their six children were born there: James Gorman Callaway, was born August 13, 1905, Minnie Callaway, was born February 11, 1907, the same year that Oklahoma became the 46th state of the union on the 16th of November. The last of the three children born at the Chimney Creek Homestead was Fred Dickerson Callaway, born there on August 17, 1909.
Minnie’s mother, America Jane (Norton) Gorman, died on April 3, 1909 and was buried in the Waynoka Cemetery. A couple of years later, in 1911 John and Minnie moved the family to her father, John Gorman’s place at Heman, Woods County, Oklahoma, several miles southeast of Chimney Creek, to be near her aging father. And, there was the added advantage of being closer to town.
During the 1880’s when the Cherokee Strip Livestock Association grazed cattle in the Cherokee Outlet, a lone butte landmark identified an area of lush grass west of the Cimarron known as the beef pasture. When the AT&SF laid their tracks, they built a section house opposite that lone butte and named the section house “Heman” for a railroad official. A town was platted, a school district was formed, and eventually a couple of stores and a feed lot opened for business there; but, the businesses did not last and only the homesteaders and cattle were left. The landmark butte and the area around it continued thereafter to be known as Heman.
When John Callaway moved to Heman, he sold his place at Chimney Creek to the McNeely family. During the McNeely family’s time at Chimney Creek, Jean Ingelow McNeely was born there on August 12, 1914. She was born in the same house where Fred Callaway had been born 5 years earlier. Fred Callaway and Jean McNeely would be married on December 12, 1931 in Alva, Woods County, Oklahoma.
After arriving at Heman, John and his son John William, with the help of neighbors, constructed a house there at the edge of an embankment about three quarters of a mile west of the Cimarron River and about a quarter mile from the AT&SF Railroad which runs parallel to the river there.
They dug a basement into the embankment with the back side opening toward the river and lined it with native stone. They then built a two-room frame house on top of the basement and anchored it to the native stone walls of the basement with heavy wire. The front of the house opened west onto the plain facing away from the river toward the butte and the basement opened to the east on the lower level behind the embankment. Upstairs, one room was John and Minnie’s bedroom and the other room was a living area during the day and children’s sleeping area at night. The lower level had a large cast iron stove and was the kitchen and dining area.
The family continued to grow, and three more children were born at Heman: Nellie Luella Callaway, born March 28, 1911; Enid America Callaway, born April 10, 1913, and Arnold Lafayette Callaway, born May 15, 1917. The place at Heman remained the Callaway family’s home for the next 19 years, until 1930.
John and his boys raised cattle and farmed at Heman and sometimes share cropped other farms for additional income. And, although money was in short supply, as it was in many rural families at that time, they did not consider themselves poor or underprivileged. Theirs was a happy family and although short of material goods they were abundantly blessed with love for each other. John loved to tease the children, especially the girls, and at mealtime, there was always conversation, fun, and laughter.
The Callaway family worked hard and participated vigorously in the life of their community. When the occasion arose, and the community asked them, they were willing to step-up and assume leadership positions and served on numerous community boards and committees.


The farming and ranching community in which the family lived was populated by a diverse group of people and like most rural communities in the west they banded together to look out for each other and help their neighbors when the occasion arose. Their neighbors were John’s brother George, the Quinlans, Graves, Kohlers, Drakes, and the Daltons among others. The Callaways were good neighbors and they were held in high esteem by those who lived around them. His friends Jim Dalton, Perry Phillips, and Jim Jones with whom he had worked on the Quinlan Ranch, were pall bearers for John Callaway when he died.
When John’s son James was 16 he began working part time for Marion Graves, a local rancher. James was an excellent hand and the two remained friends, and sometimes business partners, for the rest of Marion’s life.
When Mr. Kohler became elderly, he quit farming and ranching and moved to town so John leased his place and he and James farmed it for several years where they batched together during the summer because of its distance from Heman. Later, James acquired the Kohler place for himself and he and his wife, Naomi (Hutchinson) and their children farmed and ranched there for many years.
Again, time was moving on and the years slipped by. The children from John’s first family were adults and were now gone and had families of their own. This was a time when extended families often occupied the same household and children cared for their parents as they aged. John was no longer young, and as he was becoming more elderly, his younger children were becoming adults. His sons James, Fred, and Arnold carried more of the farming and ranching work load. Minnie, Nell, and Enid helped their mother with the domestic work. Everyone had chores to do that were based on their age and ability. There was never a shortage of work.
In 1929, at the age of 71, John helped his 20 year old son Fred acquire a piece of farm land on a lease purchase contract in the Texas panhandle outside of Dalhart, Texas. John Callaway had never learned to drive an automobile and in late summer of 1930 he decided to drive a wagon and team of horses to Dalhart and help Fred with his harvest. During the course of his trip to Texas he became ill and Fred had to bring him home.
By the time John arrived home he was very sick. It is unclear what happened to him. Some think he developed a gastro intestinal illness or had a heart attack, and some believe he developed pneumonia. Whatever his illness, eleven days after returning home John Callaway died on October 17, 1930. He was 72 years, 11 months, and 2 days of age. He was interred in the Waynoka Cemetery beside his first wife Tillie, and now rests there between his first wife Tillie and his second wife, Minnie.
After John’s death, Minnie moved to Alva, Oklahoma to make it easier for Arnold and the girls to continue their education and she continued to live there until her death on March 27, 1967 at the age of 94. John William Callaway and his wife Estella and their family lived on the Heman homestead and continued to work the place for a number of years. When John got older, he left Heman and moved his family to Waynoka. Minnie Callaway-Grover and her husband Harry bought the place and owned it for several years before finally selling it.


John Arnold Callaway was a prototypical man of the old west, a self-sufficient man of action. He was a working man who by financial standards was only moderately successful. He was not a large land owner, he had a sometimes struggling ranch business, and he certainly never became wealthy. Yet, by the most important standards by which we judge a man he was imminently successful. He was a man of character and principal who became a pillar of his community and was loved and admired by his family and friends. He was a successful father, family-man, pioneer, frontiersman, and cowboy who helped settle a wild land. He did the dangerous, hard, and dirty work that needed to be done. He was one of those men whose courage, grit, and fortitude made the cattle drives and ranches of the nineteenth century possible. He was one of those mostly nameless, faceless men who lived during the classic age of the old west; now a celebrated time in American History.
In his obituary that appeared in the Woods County Enterprise, published in Waynoka, Oklahoma, the week after he passed away, John Arnold Callaway was lauded as a pillar of the local community. He was mourned by his family and many friends and neighbors. He is remembered for his pioneering role in early Oklahoma Territory with his name engraved on “The Cimarron Cowboys Monument”, a fifteen foot long red granite stone memorial on the banks of the Cimarron River in Freedom, Oklahoma commemorating the old cowhands that helped settle the Cherokee Outlet in northwest Oklahoma.

Woods County Enterprise Weekly Newspaper Published October 1930 in Waynoka, Oklahoma Obituary of John A. Calloway Announcing the death of John A. Calloway, who was one of your old time and esteemed citizens, and who spent almost a third of a century in this community where he had raised his children and had undergone the trials and hardships of the early day pioneers an through the years following seen the wonderful development to the present, the state he had chosen for his home. John Callaway had gone to Dalhart three weeks before death to harvest crops when he was struck with intestinal flu and returned home where after eleven days he passed away. Funeral services were held at the ? church at 2:30 conducted by Rev. Grady Guy?. The large attendance was a demonstration of the respect in which the deceased was held. Burial was in the Waynoka Cemetery. His old close friends Tom ?, Jim Jones, Jim Dalton, Marion Graves, C. E. Hilton, Perry Phillips, acting as pall bearers.

John Arnold Callaway was born in Houston County Texas, Nov. 15 1857, and expired at his home in Woods County, aged 72 years, 11 months and 2 days. August 16, 1892 he was united in marriage to Tillie Douglas at Englewood, Kansas. To the marriage were born three children: Mary, Johnnie, and Caroline. After eleven brief years of happiness, Tillie was called home leaving the grieving husband and their three children and his wife’s three little girls: Jennie, Lucie, and Flora Douglas. In Alva on the fifth of September, 1904, he was again united in marriage with Minnie G. Gorman. To this union were born six children: James, Minnie, Fred, Nellie, Enid, and Arnold. He Leaves to mourn his death, a wife, 9 children, 2 step-daughters, Mrs. Jennie Ulmer, Marysville, Mo., Mrs. Lucie Williams, Conway, Kans., Mrs. Mary Duncan, Cromwell, Okla., Johnnie Callaway, Waynoka, Mrs. Caroline Harrison, Enid, James G., Quinlan, and Fred, Nellie, Enid and Arnold are still at home, one brother G. D. Calloway of Snyder, Tex., twenty grand children, 2 great grand children, a number of other relatives, and an innumerable host of friends. Eleven of the children were

called to his side, with the exception of Mrs. Flora ? who preceded him in death. John A. Calloway was a pioneer in Texas and Oklahoma and made many trips over the trail with cattle from southern Texas to northern shipping points. He was in Oklahoma and Kansas at the opening of the strip and watched the development of the Indian Territory to the present day State of Oklahoma. Note: This obituary was transcribed from an original copy in which some of the words were illegible. Where words were illegible, an appropriate word has been inserted in italic type. Additionally, in some instances where the illegible word was a person’s name, a question mark has been inserted rather than attempt to guess the name. And finally, for what it’s worth, his last name, Callaway, was misspelled in his obituary, as was often the case throughout his life.

John Arnold Callaway Family Pedigree

Peter Callaway	Before 1640	Emigrated from England
John Callaway	Born 1685	Somerset County Maryland
Edward Callaway	Born 1711	Somerset County Maryland
Isaac Callaway	Born 1750	Somerset County Maryland
David Callaway	Born 1779	North Carolina

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