American Endurance

by Richard A. Serrano

  The committee paused to take a group portrait of their nine riders (see this page). They had strapped saddlebags, bedrolls, blankets, chunks of bacon, and cans of beans on their horses and, for some, a pistol or two. Photographers from the local Foss and Eaton studio stepped up and arranged the shot. The bright flash from their big box cameras captured images that soon would brighten newspapers and magazines around the country. “A finer looking body of men and horses it would be hard to find,” the Omaha Daily Bee gushed. “They stood grouped together for the benefit of an enterprising local photographer, decked out in the accouterments of the wild and woolly west and surrounded on every side by eager friends. They presented a most picturesque sight, one to be seen but once in a lifetime.”

  Berry now had the last word. He would race with the others, he said, “but under protest.” If he won, the matter of the prize money, the new Montgomery Ward saddle, and the Colt revolver could be settled in Chicago. Buffalo Bill had been appointed to declare the winner and divide the spoils, not the crowd in Chadron and not the members of the race committee. They had long ago handed that responsibility over to Cody, who was waiting for the first of the nine horsemen to reach his doorstep, be he a cowboy or otherwise.

  But John Berry was not a cowboy. He was a railroad man. Born in November 1854 in the seaport village of Lynn, Massachusetts, he had moved west and found work with the Fremont, Elkhorn, and Missouri Valley Railroad and other lines chugging through the Nebraska Panhandle and beyond. The tracks bypassed Fannie O’Linn’s tar soddie and tiny settlement and plunked down a new depot that spawned the town of Chadron.

  In helping plat the new city, Berry set up a large booth with a small roof for shade and started selling town lots. The bidding began on a Saturday, the first day of August 1885. He and others had designed Main Street to be the commercial center, but most of the merchants and businessmen chose Second Street instead. At first it had little more than a saloon and a brace of restaurants, and they kept the doors open all night. New settlers slept in tents or under the twinkling summer stars until the railroad built a headquarters, digging earth, hammering boards, and anchoring it near the depot. Bidding was brisk, and some of the choicest lots drew ten times their value. By nightfall on the first day, Berry had collected more than $52,000 in cash. No bank had yet opened in Chadron, so he kept the bundle, which he called a “piece of money,” and slept over it for several nights. Then he hopped a construction train east to Valentine, Nebraska, and found a bank for safekeeping.

  Some recalled Berry as a “sphinx-like scout for the railroad.” Back in 1882, he had helped lay the right-of-way for another Nebraska community that he proudly named Johnstown after himself. He named some of the new roads for his family and friends—Carpenter Street for Uncle Dan and Frame Street for Jake and Elias. Over the years, he scrambled up and down the line as a land agent, surveyor, and engineer. Earlier he had driven the mail by stage to Fort Niobrara during the hostilities with the Sioux. He punched farther west, too, past Denver, searching for new train routes up and over the Rockies. He knew the region so well he did not need a map to find the quickest trail in or out of the West. After he helped pick the route of the cowboy race, the Omaha Daily Bee declared, “Rest assured that it will be the best.” Those who knew Berry’s work called him “the Pathfinder.”

  He sported a small-brimmed hat and a walrus-thick, rust-red mustache. He seemed more town-like than any cowboy, according to the Chicago Herald, which described him halfway through the race: “Nor was he rigged out in buckskin, jingling spurs, broad hat and revolvers. He was a small, thin-waisted man with a bright eye, a red mustache, a home-sick hat and a gore in the back of his $3 trousers.” Another paper observed that despite his small size, “he had all of the natural endowments for endurance.”

  He did not tolerate fools. When he was helping design a new saloon in Douglas, Wyoming, he grew weary of drunken cowboys taking target practice on his gas lamps. “There’s no particular harm in shooting out the lights, boys,” he told them. “But it strikes me you’d lose a heap of time between drinks. And no man gets a drink over this bar in the dark. He might get water by mistake, and then I’d be down to Laramie for homicide.”

  A niece, Doris Bowker Bennett, recalled in a memoir she titled A Girl in Wyoming: 1905–1922 that Uncle John was twenty years older than his seventeen-year-old bride, Winifred Howell. They stood at the altar in 1890 in Newcastle, Wyoming, three years before the Great Cowboy Race. Winifred hailed from Halifax, Nova Scotia. She and her mother had moved to her father’s log ranch house on Skull Creek on the eastern edge of Nebraska back when her father was digging for Wyoming gold. They rode out west to join him, first in a stagecoach, then in a mule-drawn wagon.

  Bennett wrote that “during the Indian wars [Berry] carried mail by stage coach through Nebraska and South Dakota.… Later he became a pathfinder for the C.B.& Q. and laid out the routes for the rails” of the old Chicago, Burlington, and Quincy line.

  John and Winifred’s marriage license was the first issued in newly founded Weston County in the newly admitted state of Wyoming, and they were the first newlyweds to board the train at the new CB&Q station. “Mr. Berry is well known all over the West having been in the employ of the railroad for a number of years as a right-of-way man and inspector of the frontier country,” noted the wedding announcement in the local Republican newspaper. “There is scarcely a ravine or hill in Wyoming or mountain that he has not visited and perhaps no man in the west is as well posted upon the actual resources of Wyoming as Mr. Berry.” The announcement called the bride “a young and accomplished lady and among the fairest of the fair.” It added, none too happily, “We don’t know what our young men are about, to allow these railroad chaps to come out here and select and carry away the fairest of Wyoming’s flowers.”

  Berry would have made an ideal catch in eastern Wyoming or almost anywhere else. “He was not a gambler, did not drink or smoke, and because of his quiet manner was known to friends as ‘Silent John,’ ” his niece Bennett wrote. “He never was a heavy eater and paid little attention to food,” all of which kept him small and lean in the saddle and a light burden for any horse, someone hard to beat on a thousand-mile run.

  Others described him as “being about as close to the classic figure of the western good man opposed to the western bad man as was possible for a creature of flesh and blood. He was slight, soft spoken, modest, hard working, intelligent and kindly.”

  A nephew, David Howell in Wyoming, said his father had helped Berry in some of his railroad surveying. “They went all through the mountains in southern Wyoming trying to find different routes,” he said. “And Aunt Winnie was a lovely lady, loved to laugh. A big, pretty, heavy-set gal. She giggled all over when she laughed.” She and John reared two daughters, Beryl and Ruth.

  Jack Hale had early on spotted talent in John Berry. The South Dakota cattleman and stock herder from near the Black Hills had also ranched under the shade of Devils Tower. He grew well acquainted with Berry’s work for the railroad carrying families and jobs to the expanding West. When Hale had offered his compromise to the Minneapolis Humane Society officials, he knew he would have a horse in this race. And when he asked John Berry to step in for an ailing cowboy and race his horse Poison, he knew Berry would do it.

  But Berry never spoke much about it. Even over the long march of years, when children begged to hear about the Great Cowboy Race, Berry had little to offer. He never told Winifred much, either. About all she ever got out of him was that somewhere in Iowa—or was it Illinois?—he happened upon a train platform and spotted a bucket of milk. Tired and thirsty, he dipped a ladle into the pail and drew out a big cup of milk.

  An angry farmer complained. “Hey, fella, that milk cost me money.” John was so sure he was going to win that he flipped the farmer a quarter. “Here,” he said. “I’ll have money to burn.”

  Some said he was racing to raise funds for a down payment on a new ranch in Wyoming, that he was short a thousand d
ollars or so. But he never spoke about that, either. He did offer one other story from the race, about when he finally came crashing into Chicago nearly dead and beaten and was put up in a hotel bed. He awoke hours later and his bleary eyes fixed on a sign someone had tacked over the doorway. “Silence!” it warned. “John Berry Sleeps Here!”

  For a sad-faced, silent man, that made him smile.

  Not so modest or soft-spoken was Doc Middleton. The former outlaw, horse thief, and rumored murderer had exercised his horse up and down the Chadron city streets for two days. Women snatched souvenir strands from his horse’s tail. They might just have likely dreamed about a lock of Doc’s beard; it fell nigh to his holsters. Or maybe they craved a more intimate look at his gold tooth.

  When Doc pulled up on his lead horse, Geronimo, a mighty yell rose from the rooftops. With his piercing, dark gray eyes under a new wide-brimmed hat, he bent low to kiss his wife, Rene, and two of their young children. Then he turned, smiled, and waved his hat to his Chadron cheerleaders. The day seemed his.

  Middleton was now forty-two years old. He once had run two criminal outfits, the Pony Boys and the Hoodoo Gang. He had been in and out of jails and prisons throughout the West, and had been ambushed and captured by a posse hired by the Wyoming Stock Growers Association. It was said he had settled down some before moving to Chadron with his third wife and their family. She was only fifteen when they had eloped in Neligh, Nebraska; he was thirty-three.

  A cowboy outlaw, horse thief, and leader of the Pony Boys and the Hoodoo Gang, Doc Middleton was the odds-on local favorite to beat them all to Chicago. (Nebraska State Historical Society)

  He was sharp with cards but nothing to talk about as a cowhand. For ranchers, he was a horse thief who fenced his loot up north. For the Sioux, he was a menace who preyed on their herds. Wanted posters featuring his rugged good looks and offering from $100 to $1,000 wallpapered the Nebraska and Wyoming countryside. He most likely was born in Texas, though his death certificate said he first breathed air in Mississippi. From the South up to northern Wyoming, he was known by a string of aliases: Dick Milton, Texas Jack, Jack Lyons, Gold-Tooth Jack, and Gold-Tooth Charley. He sometimes said his name was David, sheepishly adding that he was merely a “dealer in stock.”

  Where the “Doc” came from, no tongue could tell. His birth name most likely was James Riley, but that had to change to fit the times. His confederates were lusty, dangerous, hard-bitten toughs, men such as Kid Wade, Lame Johnnie, Lengthy Johnson, Sixteen String Jack, and Curly Grimes. A name like James Riley just was not going to cut it out west. So he became Doc to fit his own special brand of prairie house calls. He ruled his gangs with an “iron nerve,” and yet he claimed many of his ill-gotten proceeds went to helping the poor and the needy immigrants huddled in covered wagons crossing the Great Plains. Some went so far as to revere him as the “unwickedest outlaw” in the country. He considered himself a Robin Hood of the West, a Rob Roy of the Niobrara.

  Once he came across a bored cowboy at a cattle ranch shooting at the feet of an old man, making the old man dance. The old man was tiring and begging to sit down. An angry Middleton turned his guns on the cowboy and made him dance.

  Another time a greenhorn came riding past Doc in a hurry. Middleton slowed him down. “Where you bound?” he asked. “They say there’s a damned old horse thief named Dick Milton who is scaring everybody,” came the reply. “I sure wish I could get a look at him. He wouldn’t scare me.” Doc drew his pistol. “Young man, you’re talking to Dick Milton.” Then he took the greenhorn’s guns and stole his horse.

  On a Union Pacific train out of Denver, Doc elbowed into a twenty-five-cent-limit game of poker. Out the window, someone spotted a line of free-range cattle, and one of the gamblers, a Texan named J. S. Robb, swung around and took a long look. When he turned back to the game, Robb noticed he had drawn four kings.

  “If the limit was off, I would bet $5 on this hand,” Robb said. “If you did,” said Middleton, “I would raise you $10.”

  They quarreled a bit and upped the wager to $15. Middleton then turned over four aces. Robb instantly realized he’d been had. He placed his six-shooter on the card table. “My friend,” he told Middleton, “I guess I will have to trouble you to hand me back that money.”

  Doc had stolen his first horse at the age of fourteen. Word spread that he had shot and killed a soldier in a dance hall brawl, clubbed a man to death for threatening his grandmother, and fatally beat and whipped a cowhand during a squabble inside a Texas corral. At eighteen he murdered a schoolteacher for defiling his sister. In a Huntsville, Texas, prison for horse stealing, he broke out and fled the Lone Star State for good. Others said that when he was twenty he killed several men in Newton, Kansas, for murdering the town marshal, a man who had befriended the young Doc.

  During a two-year spree in the late 1870s, Middleton and his Pony Boys and Hoodoo gangsters stole more than three thousand horses, mostly along the Niobrara River Valley. When it was forbidden to sell whiskey to the Indians, he shipped wagons full of chicken carcasses to the reservations, the chickens stuffed with half pints. When the railroads replaced the cattle drives, he stole from the cattle cars.

  Stories circulated through Nebraska, Wyoming, and the territories that Doc and his gangs hid in dugouts along the Niobrara, well beyond the reach of the law. “A great many efforts have been made to capture Doc Middleton,” the Daily Leader in Cheyenne, Wyoming, reported in April 1879. “But as yet he is still at large. He has had many escapes and adventures and is regarded as the luckiest outlaw who ever infested the western frontier.”

  Tall and handsome, elusive and ornery, for a while he led as many as a hundred bandits terrorizing the countryside. “He has no education but is a smooth talker, and was born to command,” according to the Cheyenne Daily Sun in 1879. “He is loved by his men and yet they fear him.… He carries two trusty revolvers and is regarded a dead shot.” Some called him the “Man with the Golden Tooth” after part of a tooth was chipped out and rebuilt with gold filling. Others mocked him as “the golden-toothed lover of other folks’ cattle.”

  The railroad magnates and the stockmen at last did him in. He was run to ground in a canyon shootout that ended with two of his gangsters dead and a lawman seriously wounded. The authorities took Middleton into custody and sent him up for grand larceny and stealing horses. He pled guilty in a Cheyenne courtroom, and the judge gave him five years. They slapped handcuffs on his wrists and led him away in a horse-drawn bus to the railroad depot and from there to prison. Crowding into the bus with Middleton was a well-armed security detail—a deputy warden, a sheriff, a deputy sheriff, a police officer, and, carrying just his notepad and pencil, a Cheyenne newspaper reporter.

  Doc did not much seem to care; little of it fazed him. Being escorted to prison seemed mostly an inconvenience. “It’s pretty hard,” he mused in the bus. “But I’ve made up my mind to take it philosophically. I expect that five years down there will seem as long as ten out here on the free prairie.”

  They were taking him to the fairly new Nebraska State Penitentiary in Lincoln because a fire had closed the Wyoming Territorial Prison near Laramie. What was left of those burned walls and charred cinder blocks did not seem likely to hold someone as mean and treacherous as Doc Middleton. Deputy Warden C. J. Nobels told him that many of the Wyoming prisoners liked the Lincoln facilities. Nice new quarters, they said; easy street. “Well,” said Middleton, “I’m glad to hear it. I’m not used to being caged up that way. I don’t think my punishment is just.” To read the Nebraska papers, he complained, “you would think I’m the worst man in the world.”

  The reporter asked why his wife had not come to Cheyenne for one last kiss before he was hauled off to prison. The question stopped Middleton. For all his toughness and defiance, Doc let out a long, pitiful sigh. His voice trembled, and he began to cry. “Because she didn’t intend to come,” he barked back. “I did not expect her. There was no truth to the report that she was on he
r way to Cheyenne. That was another lie.”

  Middleton made parole in just under four years and returned to his hard-won turf on the Nebraska Panhandle. He seemed bent on going clean, on starting fresh, on living his life on the square. For a while he managed a saloon and dealt poker, dusting off his newfound city manners in Nebraska towns such as Valentine and Gordon and eventually Chadron.

  By the time the Great Cowboy Race came along, he was trying hard to fit in. Even the Chadron Democrat was amazed to report that “Middleton was walking the streets of Chadron looking as bland as a Sunday School missionary.” Others found him more like a “mild Methodist circuit rider.” He sought signatures on a petition to get himself appointed Chadron’s night police watchman. But some wag at a city council meeting blurted out, “Hell, you can get a petition to hang a man!” The appointment was voted down. But Middleton did manage a temporary job as a “special” night watchman, assisting the town constable “in times of need.”

  The new Doc Middleton craved acceptance in the emerging new West, even as his outlaw past shadowed him around town. At Billy the Bear’s gala wedding in Chadron a year before the cowboy race, Doc presented the couple with an expensive silver spoon and vase. He signed the wedding registry, rather properly, as “D. C. Middleton.”

  With nine horsemen about to tear off for Chicago, all the smart Chadron money was riding on Doc Middleton to win. None of that, however, meant another hometown favorite was counted out.

  Joe Gillespie sat on his horse, Billy Schafer, next to the others, the biggest cowboy, the strongest of them all, and the oldest at forty-three. Josiah Bankston Gillespie’s brother was a well-respected Dawes County physician; his niece was Temperance, the beautiful bride of Billy the Bear. Gillespie had ties rooted deep in Nebraska soil and branching throughout the Chadron community. He was known affectionately as “Old Joe” for his gray sideburns and white handlebar mustache as well as his raw, rugged Western determination. In any challenge he undertook, Old Joe aimed to win.