It was almost eight in the morning on June 3, 1895, when Jennie Freeman and Belle Black rode into the quiet, unassuming town of Fairview, Oklahoma.  The women, who would later be described by the people they robbed as “neither young, fair, nor dashing”, steered their rides toward a large, brick building that was a combination mercantile and post office.  Although few paid much attention to them, the women smiled politely to passersby going about their daily routines.  When Jennie and Belle reached the store, they tied their horses to a hitching post in front of the business and went inside.  

A handful of customers browsed through the assortment of merchandise on display, blankets, canned goods, material, brooms, etc.  Belle and Jennie did the same.  Jennie concentrated on the back of the store and Belle the front.  She lingered around a long counter near the entrance, inspecting a decorative row of lady’s hats laid across it.  She tried one of the hats on then reached for a nearby hand mirror to check her look.  Belle glanced behind the counter and spotted a rifle leaning against a back wall close to the cash register.  She caught Jennie’s eye as she removed the hat and put it back in place.  

Jennie inconspicuously scanned the shelves and barrels around the section of the room where she was at.  A pair of six-shooters resting on a table next to several neatly stacked cans of chewing tobacco gave her pause.  She gave the weapons a closer look.  They were new, unloaded guns with price tags hanging from the barrels.  

After a several minutes shopping, both women strolled nonchalantly toward the exit.  A store clerk called out to them just before they reached the door.  “Was there something I could help you ladies find?” The courteous man asked.  “Now that you mention it,” Belle said as she stopped and turned around.  “That lovely hat on the end…,” she said, pointing.  “How much is it?”  The clerk walked over to the item Belle referred to and she followed him.  The clerk located the price tag, tucked inside the brim of the bonnet, and showed it to Belle.  She studied it for a moment then sadly shook her head.  “Thank you for your help,” she said as she headed for the exit. She glanced thoughtfully back at the hat one last time before joining Jennie, waiting for her outside.   

The two women climbed onto their horses and rode out of town in the same slow, deliberate fashion they arrived.  Jennie smiled at Belle and patted the rifle cradled in her lap.  The gun was the same one that had been sitting behind the register at the store.  Jennie had stolen the rifle.  Belle almost laughed.  

Five hours later Jennie and Belle returned to Fairview.  When they arrived the second time, they were wearing men’s clothing and accompanied by outlaw Zip Wyatt and his gang.  They helped the desperados rob the mercantile and post office and stole three horses while making their getaway.  

According to the August 14, 1895, edition of the Hutchinson, Kansas newspaper, The Hutchinson News, Jennie and Belle had participated in numerous robberies with Wyatt and his men.  The women knew their jobs well.  Prior to holding up a post office or a store, the women were supposed to ride to the appointed location to determine how many armed men were on the scene.  If they found any unattended guns, they were to take them.  Jennie and Belle would then use the weapons in the robbery.  

The Hutchinson News described Jennie Freeman as a sinister looking woman, tall and slender with snapping black eyes, and thick black hair.  Her husband, Matt became a member of Zip Wyatt’s gang in 1891.  Nathaniel ‘Zip’ Wyatt was a murderer and a thief from Indiana.  He, and his fugitive followers, was responsible for a variety of crimes committed in Kansas, Illinois, and the Oklahoma Territory from June 1891 to July 1895.  They robbed trains, stole cattle, and killed more than eleven men in the process.

Federal officers arrested Wyatt’s in July 1891.  He escaped from the jail in Guthrie, Oklahoma, where he was being held on December 31, 1892.  A thousand-dollar reward was offered for Wyatt’s capture.  A posse was quickly organized to track the desperado, but he managed to elude law enforcement hiding near the Cimarron River in Major County, Oklahoma.  Changing his name to Dick Yeager, Wyatt sought refuge at the home of aspiring outlaw, Matt Freeman.  Freeman owned a horse ranch in northwest Oklahoma.  For more than four months, the rancher and his wife, Jennie provided Wyatt with all the comforts he required.  Wyatt and Jennie became romantically involved and shortly after his partner in crime arrived, Isaac ‘Ike’ Black and his wife, Belle, the four abandoned the Freeman home.  

Unusual though it was at the time to have women gang members, the ladies proved to be valuable asset.  After other members of the Wyatt-Black gang were recruited, plans were made to steal cattle and horses and drive them into Texas to be sold.  Jennie and Belle helped the men with their efforts by carrying messages and supplies to their various camps.  

The Wyatt-Black gang found a permanent hideout near the head of the Salt Creek canyon.  It was a large cave that had at one time been used by the Dalton gang.  According to author and historian, Glenn Shirley, the drifting sands of the Salt Plain, Oklahoma area, “rapidly obliterated a trail and made it impossible for a posse to follow.”  The cave had two entrances.  The outlaws stayed in the front part of the cave because they could look out and see any enemies approaching from a long distance away.  The horses the gang stole were kept in a corral in the back of the cave.  

The Wyatt-Black gang robbed from logging operations, freight wagons, and settlers traveling through the region.  Newspaper accounts about their crime sprees, as told to reporters by victims, noted that the outlaws consisted of four men and two women.  According to the November 7, 1895, edition of the Wichita, Kansas newspaper, The Wichita Eagle, “Belle Black was not a handsome woman by any means, yet she is lithe and has a keen eye….  Mrs. Freeman is small in stature and quite handsome.  She wears her hair short, and it curls around the bill of her cap.  Both Mrs. Freeman and Mrs. Black led raids on several occasions, and in bravery and daring were not second to any member of the gang.”  

By 1895, the Wyatt-Black gang’s lawlessness had become so commonplace throughout the Oklahoma Territory that storeowners and homesteaders organized chapters of the Anti-Horse Thief Association.  Law enforcement officers like U.S. Marshal Bill Tilghman were encouraged by politicians and landowners to make apprehending the gang top priority.  The April 14, 1963, edition of the Guthrie, Oklahoma newspaper, the Guthrie Daily Leader, Marshall Tilghman described the job Jennie and Belle had with the gang.  “The two women traveled with the team and covered wagon [Wyatt and Black on horseback],” the marshal explained.  “They would establish camp near some country post office or store and make some purchases of canned goods or other supplies…survey the place thoroughly and note if there were any Winchesters or shotguns setting behind the counter, then go to camp and report to Wyatt and Black who, as soon as night came, would ride to the store, hold up the proprietor and loot the place….  They would then ride off in the opposite direction from the camp, make a circuit and go back, hitch up their team and ride behind the wagon as lookouts.  Next morning, they would be miles away…. [There was also a brisk demand for horses for farm power and other uses] and occasionally they would steal a good team, leave the women in camp, and run the horses up the Kansas line and sell them.”

On November 18, 1893, the Wyatt-Black gang robbed the Hightower Store and Post Office in Arapaho, Oklahoma.  On March 28, 1894, they robbed the general store and post office in Blaine County, Oklahoma.  Edward Townsend, the owner of the store was shot and killed in the holdup.  One of the murderers was tracked to his relatives’ home in Logan County, Oklahoma.  The marshal in charge of the arrest tried to persuade him to tell police where Wyatt, Black, and the other gang members were hiding but he refused.  The shooter was tried, convicted, and sentenced to life in jail.  

Despite the loss of one of their members, the Wyatt-Black gang continued on with their nefarious ways.  Throughout April and May 1894, Jennie and Belle helped Wyatt and Black steal pension funds and livestock from farmers throughout northern Oklahoma.  The outlaw women were finally apprehended for their misdeeds on June 4, 1894, by law enforcement agents who followed them to their cave hideout.  According to the June 27, 1895, edition of the Kingfisher, Oklahoma newspaper, the Kingfisher Free Press, “Belle Black and Jennie Freeman were captured as they attempted to escape from a dugout near the cave where the outlaws quartered…and when searched they had in their possession money and valuables taken from the [Fairview] post office.”  

Zip Wyatt and Ike Black managed to escape the June 1894 raid on their hideout, but they were injured in the process.  Wyatt was shot through the left arm and Black was shot in the right heel.  

In late October 1895, Jennie and Belle were taken to Alva, Oklahoma to appear before a grand jury.  The November 7, 1895, edition of the Alva Republic reported that “after a thorough examination, the women were discharged without indictment.”  The newspaper noted that the jury found no evidence of “a criminal nature against the women, other than the fact that they were present with the two outlaws.”

Given the rarity of women outlaws at the time, newspaper, and Dime novels, carried story after story about the lady renegades and the lives they lived.  Prior to Belle and Jennie being released from the jail in Guthrie, Oklahoma, the women were the center of attraction for many visitors.  “Unlike the female bandits of romance books, these female outlaws had their own manner of dress,” the August 14, 1895, edition of the Hutchinson News noted.  “Instead of being dressed in the dashing cowboy garb, they wore the attire usual of the wives and farmers and working men, save that one wore boots and spurs to aid her in urging her horse when attempting to outride the deputy marshals.”

The May 30, 1896, edition of the Fort Wayne, Indiana newspaper, the Fort Wayne Sentinel, reported that Belle Black and Jennie Freeman were “victims of circumstances over which they had not control.”  “The capture of the female bandits dispelled the popular myth of the lady bandit,” the newspaper story continued.  “Neither woman has the appearance of a desperate criminal.  Mrs. Freeman, who eloped from her husband with the leader of the gang has defied sheriffs and has robbed right and left.  It was not known that Mrs. Freeman or Mrs. Black were women during the raids because the two women always dressed like men.  

“Mrs. Black and her husband came to western Kansas six years ago and were financially embarrassed through failure of crops.  They took to stealing cattle and were obliged to hide to escape arrest.  A gang of desperadoes gradually joined them.  Zip Wyatt, the leader, was a cowboy who came to Guthrie once a month to spend his wages in high living and it was here that he met Mrs. Freeman, who was an Illinois girl who had formed an incorrect idea of the glories of a bandit’s life from too many trashy novels.  He persuaded her to elope with him after he had killed two or three men and gone into hiding.  He has often puzzled the sheriff as they have fired their rifles at him point blank, and he has escaped without injury. 

“Since her capture, Mrs. Freeman says Wyatt always wears steel plates over his back, front and thighs and will never be taken alive.”

On August 1, 1895, Zip Wyatt and Ike Black were overtaken by a posse four miles outside of the town of Cantonment, Oklahoma.  Black was shot in the head and killed.  Wyatt was captured after being shot in the chest by lawmen.  Before dying of his wounds at the Enid, Oklahoma jail on September 7, 1895, he admitted to killing eleven men.   According to a report by Marshal Bill Tilghman that appeared in the August 14, 1963, edition of the Guthrie Daily Leader, Jennie Freeman became an evangelist and preached throughout the same section of country where she rode and scouted with the Wyatt-Black gang.  Belle Black moved to Missouri where she married a successful farmer.  Belle and her husband had three children and she became a respected member of the community.