Cowboy Pioneer

Rex A. Reynolds

Life of A Cowboy

A Biography of John Arnold Callaway 1857-1930


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, April, 2015



This biography is dedicated to the many descendents of

John Arnold Callaway

and, to the larger Callaway Family.


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 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 as 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 1836, before John's father, James, came to Texas, in the Texas War for Independence, Sam Houston had defeated Santa Ana's troops, but those troops were not the bulk of the Mexican army and hostilities continued periodically between Houston's Texas troops and the Mexican Army until a formal armistice was reached between the Mexican Government and the new Texas Republic in 1843, ending the Texas War for Independence.

In 1839, James Callaway came from Georgia to Colorado County, Texas, West of present day Houston. Shortly after he arrived, he 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.

John's mother, Elizabeth Dillard, had come from Tennessee to Houston County, in East Texas, with her family, in 1835, and in about 1844, after the armistice with Mexico, James moved to Houston County. After arriving in Houston County, James and Elizabeth met and they began a courtship and 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 a successful 14 year partnership, in 1860 William Dillard died and James was appointed executor of his estate. His responsibility was 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.

Then, after the civil war began, (1861-1865), the Confederacy requisitioned cattle and other livestock belonging to 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's Civil War began, and the combination of the war and the death of his maternal grandfather the year before, effectively 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 1866 or 1867, on to DeWitt County, Texas.

John spent his childhood, and attended school, in DeWitt 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 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 DeWitt 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 Territory. 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 together on 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 driving cattle 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 recorded there. Some of the men whose names are on display there, like Jesse Chisholm, and Charley Goodnight, are legendary; but, most are men whose lives are lost to history.

Following here are the name of eleven of these stalwart men who rode the cattle trails 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 became the man he was when he reached adulthood, it is also 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 hard wood trees, mostly blackjack and post oak, which bisected what, would become the State of Oklahoma diagonally into 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 mostly be Indians that had been resettled there from east of the Mississippi River, 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, Arapaho, 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.

The Indian Nations: Oklahoma Territory and Indian Territory

It is crucial to understand that long before the white 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 for 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 native 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. 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.

General Philip Sheridan, in command of the U. S. Army's Department of the Missouri in 1868, decided to send Lieutenant Colonel, General Armstrong Custer, and the U. S. Cavalry into Oklahoma Territory for a winter campaign to pacify hostile Indian tribes there.

During his winter campaign of 1868, Custer massacred Black Kettle, a Cheyenne peace chief, and his village of Southern 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, children, and the elderly, and their massacre would enrage the plains Indians.

A story has been told that sometime later during a Sacred Medicine Arrows ceremony, Custer had pow-wow with Cheyenne Chief Medicine Arrows (aka: Stone Forehead) who rebuked him for the massacre of Black Kettle's village and then, after smoking the pipe with him, insulted him by emptying the pipe's ashes on his boots. During the ceremony, Custer pledged he would not to kill Cheyenne people in the future. The chief then warned Custer that if he should break his word, his life would be forfeited, a forewarning, some say a prediction, of his death.

In June of 1874, Cheyenne and Comanche warriors were rebuffed after attacking heavily armed buffalo hunters at the battle of Adobe Walls in the Texas panhandle, a part of the multi-year Red River War with the U. S. military. Then, after having gone unconquered for years, that winter (1874-1875), they were defeated by Ranald Mackenzie, 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 the next 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. Quanah added his mother's surname, Parker, to his Indian name as a tribute to his mother and in recognition of his white heritage.

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 Rose bud and then, in a pitched battle, 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 and death.

After the battle, the Sioux and Cheyenne women mutilated the soldier's bodies, as was their custom; but, they only striped Custer's body naked and pierced his ear drums with sewing awls. When asked later why they had pierced Custer's ear drums, they said it was done so he would be able to hear better in the next life, since it seemed that he had been unable to hear Chief Medicine Arrows warning, that he would die if he broke his word not to kill Cheyenne people in the future, a promise that he had made under the Sacred Medicine Arrows at the ceremony.

Later, when the Sioux and Northern Cheyenne were finally subdued, Sitting Bull, Crazy Horse, and 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).

In Arizona, New Mexico, and Texas the Apache wars continued non-stop from 1849 until 1886, when the U. S. Army and Kit Carson defeated the Navajo in the battle of Canyon de Chelly and destroyed their winter food supplies. In later actions, war leaders Mangas Coloradas, Cochise, and Victorio from other Apache tribes were defeated. And finally, General Crook and General Miles with the U. S. Cavalry made life so impossible for Geronimo and his band of Chiricahua Apache that they surrendered and were relocated to Florida and later to Southwest 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 whit 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, sometimes called the Wild Bunch or Oklahombres, the Dalton gang, the Younger gang and the black and Indian gang of Rufus Buck. They were also the home of the renegade Indian outlaws and serial killers, such as, Cherokee Bill and Blueford 'Blue' Duck.

Many of the men who lived and worked in the west were rough and hard living, with little regard for society's rules. And, between periods of law breaking, or as a way to hide from the law, some outlaws, like Bill Doolin, sometimes worked as cowboys. So, in addition to the inherent dangers of a cowboy life, like wild longhorn cattle, treacherous rivers, dangerous terrain, and hostile Indians, John Callaway was also forced, by necessity, to associate with men who were intemperate and not of the highest character. A few men he knew, and with whom he had at times worked, and were, or would later become, outlaws, were Bill Doolin, who was a rustler, bank robber, stage and train robber; several Dalton brothers, two of whom were killed robbing a bank in Coffeyville, Kansas; and Sam Bass, who became a train robber after working for John when he managed a livery stable in the Texas Panhandle.

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 to the Indian Nations. And, as an example, he told his sons the following story of an incident that happened to him in Dodge City, Kansas while he was still a teenager.

It seems he had found himself in the wrong place at the wrong time. His cattle trailing outfit had arrived outside 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. One group appeared to be lawmen; but, he had no idea who the others were.

The store clerk suggested he stay in the store until whatever was going to happen was over. But, John was anxious to get going and said he thought he would be able to get out of town before any trouble started; so, the clerk saw him out and locked the door behind him. He quickly realized he had made a mistake and he would not be able to get past the combatants, and now he had no good place to take refuge. So, to get out the of way, young John escaped up an alley between two buildings, where he could wait it out, away from any gun fire. During the confrontation a group of men came up and 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 hill country of West Texas, John had come upon a cowboy who was in the process of branding calves. As he 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 he 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 they let him continue on his way. Again, he had been lucky.

In conversations with John's sons, they marveled that their father was able to survive so many dangerous situations, under grave circumstances, and they expressed amazement and admiration for his ingenuity, his depth of knowledge and his wisdom. Several of his children related the above incident as an example.

They said that when John related what he believed to be life and death incidents, 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. He learned to be cautious and to realize that things are not always what they appear to be.

Considering this particular incident, what are the specific lessons it contains? First, one should recognize that branding cattle is fundamentally a group activity, and that it would be highly unusual for one man alone to be branding cattle in an isolated location, and it should be highly unusual for one man alone to be branding cattle in an isolated location, and it should arouse suspicion. And, further, if a person was sufficiently aware, they would probably sense that something was not quite right as they approached and they should not dismiss feelings of doubt; but pay attention to their suspicions and not be distracted by other desires, such as, his eagerness to show off his roping skills. And, in this case, the best course of action would have been to tip his hat and continue on his way.

In general, John would appear to have learned from these incidents that, if something does not seem quite right, there is a good chance that it isn't, and healthy suspicion is a good thing. Moreover, a person should condition themselves to be aware at all times and to think critically and analyze every situation, and to pay attention to feelings of uneasiness. And finally, one should approach each situation with caution and not dismiss concerns lightly; because, they are important to your safety, and maybe to your life. And if you conclude that things are not as you think they should be, you should act conservatively, cautiously, and decisively, not recklessly.

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 John lived and worked. He obviously learned his lessons well, because he avoided making the same mistake repeatedly, and in the era in which he lived, you could not always count on being lucky, you needed to be smart, cautious and wary in order to increase your chances of survival. And, perhaps the best proof that he learned these lessons well is, that he survived and lived to be an old man.

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