The Top 5 Most Notorious Outlaws Read online

  When the Civil War finally broke out in 1861, the border states of Kentucky and Missouri became even more important. By remaining neutral and not seceding, they became battlegrounds between the Union and Confederate forces, and Kentucky was so important that President Lincoln himself famously said, “I hope to have God on my side but I must have Kentucky.”

  The unsettled nature of the politics also dictated the nature of the fighting there, which would be dominated by guerrillas and “bushwhackers”. By 1862, the battle lines in the Western theater had shifted well south of Missouri, leaving it firmly in Union control. Frank James joined the Confederate army, but when the Union dominated the rebel forces in Missouri, Clay County became occupied territory. Meanwhile, the state had its own militia and took the position that anyone associated with the Confederacy was a traitor. Anyone believed to be a Confederate or assisting the Confederacy risked a raid from the militia.

  Thus, Confederate sympathizers fought what could loosely be called a counterinsurgency, sparking savage guerilla warfare in the woods and fields of Missouri. Cattle were confiscated on behalf of the Union, houses were burned, and pro-slavery sympathizers were lynched on their own property. Union civilians were murdered in their own fields in retaliation.

  By 1864, the violence within the state began to slow down, but a small, militant faction remained committed to aggression against the Union for humiliating the Confederates, as well as persuading others from supporting the federal government. Known as the bushwhackers, the guerilla soldiers of western Missouri operated outside of the chain-of-command of the Confederacy, seeking vengeance with no small dose of extreme violence.

  Frank joined one of the dozens of bushwhacker groups, with Jesse, now 15 years old, sometimes serving as a messenger between his mother and the band of guerillas Frank rode with. When Union soldiers came to the Samuel-James farm to get more information on Frank’s location, Rueben initially would not comply. However, when the Union men strung him up and hung him from a tree, with Zerelda standing nearby, unleashing a verbal barrage upon the Union militia, Rueben eventually gave in and led the men to the bushwhackers’ hiding place. The militia interrupted a poker game and the guerillas scattered. Frank got away with some of the other men, leaving two dead bushwhackers behind. After the bushwhackers regrouped, they were attacked again and lost more men in the fight.

  Though he ultimately relented and gave the Union militia the information they wanted, Rueben was taken to Liberty, Missouri and jailed for aiding the Confederacy. Soon after that, he was transferred to St. Joseph. He was paroled on June 24, 1863. Zerelda was paroled in St. Joseph on June 5 after she signed an oath pledging her loyalty to the Union, which she, of course, had no intention of honoring. A letter dated July 8, 1863 was found in Rueben’s file with the provost marshal and was signed by three neighbors. It addressed the incident at the farm and his initial refusal to assist the Union men, which led to his arrest. The letter said:

  “In the case of Dr. Reuben Samuel, held as prisoner by the military, to report at Saint Joseph, we his neighbors, desire to state that we regard him as a peaceable, quiet, and inoffensive man, who would harm no one. He is, we hesitate not to state, under the control of his wife [and] stepson, and is really afraid to act contrary to their wishes on anything. This fear, we believe, caused him to make a false statement, which he would not, otherwise, have done. We know no man who is more peacefully inclined and who is more inoffensive. We therefore request you to discharge him.”

  Though Jesse wanted to join his brother with the bushwhackers, he was brushed off as being too young, not to mention the fact he had other responsibilities at home with his parents in jail and a tobacco farm to tend. It did not help his cause when he blew off the tip of a finger cleaning a gun, earning him the nickname “Dingus” from the guerillas.

  It is believed that Jesse finally got his chance to join up with the bushwhackers in the spring of 1864. Lt. Charles “Fletch” Taylor was in Clay County on a recruiting trip and likely encountered Jesse at that time. As a bushwhacker, Jesse saw violence on a horrific level. Men were not simply murdered, but some were scalped or disemboweled. Other Union men had their noses and ears cut off, their skulls crushed, or their throats cut. Fighting occurred at close range with revolvers rather than rifles. Bushwhacker units often carried multiple guns with them, allowing them to fire off six shots from one gun, six from another, and sometimes, six more shots from a third revolver, all at close range. Jesse survived a gunshot that passed through his upper chest and out the other side of his body. He was taken to Kansas City and spent two months recuperating at the home of his uncle, John Mimms. His cousin, Zee, kept a close watch over him until he was ready to return to the fighting.

  The man who served as Jesse’s mentor was a cold-blooded psychopathic killer named William T. Anderson, also known as “Bloody Bill.” Before the Civil War, Anderson was a horse thief, and when it began he was part of the pro-Union “Jayhawkers” before he switched sides and worked with William Clarke Quantrill, perhaps the most famous bushwhacker in the region and considered by many to be the most vicious killer of them all. It is believed that Frank James may have also been part of Quantrill’s Raiders, which became notorious for the August 1863 massacre of 200 men and boys in Lawrence, Kansas, an abolitionist center. Jesse’s mother would later name her daughter Fanny Quantrill Samuel after the notorious killer.

  Bloody Bill Anderson

  Quantrill

  In the summer of 1864, Jesse joined Anderson, who led his band of guerillas on a murderous rampage. Known to decorate the saddle of his horse with Union scalps, Anderson was not afraid to take risks and start a fight even if he was outnumbered. His campaign of violence peaked in Centralia, Missouri on September 27, 1864, when he led a group of guerilla soldiers into Centralia and pillaged the town, murdering 22 unarmed Union soldiers along the way. When over 100 Union soldiers pursued the rebels, Anderson and his men were waiting and successfully ambushed them, killing even those who attempted to surrender. Many of the soldiers were tortured, and some were beheaded. This bloody massacre was Jesse’s introduction to a violent life that he would never leave behind. When Anderson was caught and killed near Albany, Missouri a month later, a rope that he used to track the number of murders he was responsible for had 54 knots.

  After the Centralia massacre, Zerelda was very proud of her sons, never swaying from the belief that they were Confederate heroes. However, in January 1865, Rueben and Zerelda received official orders from the Headquarters of the Department of Missouri accusing Zerelda of being disloyal to the federal government. She and her family were ordered to go under the supervision of an armed guard to either Memphis or Little Rock, whichever location they chose. However, they opted to hide out in Rulo, Nebraska, where Zerelda may have taught school and Rueben might have tried to revive his medical practice. They did not return to Missouri until the Civil War was over.

  As the war finally drew to a close in April 1865, the bushwhackers initially did not believe it and thought it was just another Yankee lie. However, even after it was verified, Jesse James and the bushwhackers did not quit fighting on behalf of the Confederacy. After heading to Texas with Anderson’s bushwhackers near the end of the war, Jesse returned to Missouri in time for a Wisconsin cavalryman to shoot him during a skirmish in May 1865, sending a bullet through his lung. Jesse was sent back to Kansas City to recuperate once again and made his way to Rulo, no doubt under the care of his stepfather. He was also tended to by first cousin Zerelda Mimms, who was named after Jesse’s mother, and nearly a decade later Jesse would make her his wife. During his recuperation, according to his mother, Jesse said that he did not want to die but, if he did, he did not want to be buried in a northern state. She vowed that would not happen.

  In May 1865, Missouri crafted a new, voter-approved state constitution. The state’s slaves were freed and in order to vote, men had to take an oath verifying that they had not committed disloyal ac
ts against the United States. This resulted in sweeping changes in local politics, including in Jesse James’s home county, as any last vestiges of the Confederacy were removed. That August, Zerelda and her husband returned home, and soon after that Jesse and Frank joined her. As Missouri politics shifted toward an acceptance of Union values, particularly regarding emancipation, Jesse and other guerilla fighters resisted. While some former Confederates were able to move forward, Jesse either could or would not. He, like many of the other bushwhackers, viewed himself as a victim and believed he was being persecuted because of his role in the Civil War. Thus, the resistance of the bushwhackers would continue, albeit in another form.

  Chapter 3: A Bushwhacker Becomes a Bank Robber

  The war may have been officially over, but it was not over as far as the guerilla armies were concerned. Bushwhackers were believed to have been responsible for the theft of $58,000 from the Clay County Savings Association in February 1866, and after Jesse became famous he was tied to that robbery, but there is no evidence to support that Frank or Jesse had anything to do with it. Nevertheless, the fact the bank was owned and operated by Republicans who had been part of the Union militia made it a clear target for bushwhackers.

  The Clay County Savings Bank

  There were a string of bold armed robberies in broad daylight conducted by bushwhackers that Jesse was associated with, particularly Archie Clement’s men. In later years, eyewitnesses to some of these robberies would claim that the James brothers participated, and after an 1867 robbery one man claimed “positively and emphatically that he recognized Jesse and Frank James … among the robbers.” Still, there was no clear connection made between a bank robbery and Jesse James until December 7, 1869. Jesse was on the lookout for Samuel P. Cox, the member of the Union militia that killed Bill Anderson. Jesse and another man – most likely Frank - went to Gallatin, Missouri and robbed the Daviess County Savings Association after asking for small bills in exchange for a 100 dollar bill. During the robbery, respected community citizen and family man Captain John W. Sheets was fatally shot in the heart and head. Sheets was working as the bank’s cashier, and Jesse mistakenly believed that Sheets was Cox, so he murdered Sheets on the spot while getting away with less than $1,000.

  Although the James brothers managed to escape and get out of town, Jesse bragged about avenging Bloody Bill’s death to anyone who would listen, despite the fact he was wrong. Naturally, that had the effect of implicating him in the robbery and murder, and Gallatin was in an uproar. The governor of Missouri offered a reward for the capture of Jesse and Frank, and the St. Joseph Gazette provided details of the robbery and murder. Mentioning Jesse and Frank by name as the suspects, the article marked the first time that Jesse’s name appeared in print in connection to a crime. It was exactly what Jesse had been waiting for. For a man who spent much of his brief life seeking attention, he had it now, and with the help of a newspaperman from Kansas City, Jesse James would soon become a household name.

  John Newman Edwards was a former officer in the Confederate army who worked as an editor at the Kansas City Times. An alcoholic who was still bitter over the war, he was eager to stir up the former Confederates within the Democratic Party. His interests were purely political, as he wanted the ex-Confederates to resume their place of power. He saw the story in the Gazette about Jesse and Frank James and, with it, an opportunity to spread propaganda about the former Confederates of the Civil War, which in turn could potentially help his cause. He had already shown no hesitancy to portray armed rebels as victims of radicals from the North.

  Edwards

  Edwards met with Frank and Jesse and quickly realized that Jesse sought the limelight far more than Frank did. Jesse possessed almost an urgency to be noticed and this played well into Edwards’ desire to create a story about the unfair treatment of ex-Confederates. About six months after the robbery in Gallatin, Jesse wrote an open letter to the governor, which Edwards printed in the Times. Jesse claimed that he was innocent of the charges against him and that the Union men were the true criminals. Jesse said that he was being unfairly cast as an outlaw simply because he held beliefs that were different from the Union. The creation of the mythical Jesse James was underway.

  It was Edwards who started the myth that Jesse was the modern day Robin Hood who stole from the rich to give to the poor. In 1873, he devoted 20 pages to the James gang, glorifying their achievements as noble and for the greater good. Jesse was so enamored with the image that Edwards would create for him that he named his son, Jesse Edward James, after Edwards, although Jesse, Jr. was known as Tim. To make sure there was no doubt that he had been there, Jesse even took to leaving press releases at his crime scenes. He had no difficulty trying to live up to the image Edwards created, usually dressing in style and carrying a Bible that looked like it had been referred to often.

  Chapter 4: The James-Younger Gang

  The Younger Brothers and their posse

  The James brothers had certainly committed their first notorious robbery before the end of the decade, but they were just getting warmed up. Even while Jesse was asserting his innocence in papers, the James brothers were forming a gang of robbers by linking up with the Younger brothers, Cole, John, Jim and Bob. The James-Younger Gang would also include Clell Miller and other former Confederate guerrillas and sympathizers. As the most notorious and the one with a public persona, Jesse became the face of the group, and though he was often assumed to be its leader, it appears the group shared power and decision-making.

  Cole Younger

  Cole, Jim, John, and Bob Younger formed the core of the James-Younger gang along with Jesse and Frank. Other men came and went from the group, participating in various armed robberies that occurred over Jesse’s 15-year run as an outlaw. The James and Younger brothers moved freely about their home turf in Missouri. Thanks to Edwards, the public was convinced that the gang was on a noble pursuit. They not only did not turn the gang in, they helped shield them from the law, making the task of finding Jesse and his gang very difficult for Missouri authorities. This coincided with ex-Confederates winning back their seats in the state Senate. The conditions were ripe for the mythical Jesse to flourish.

  It is no coincidence that Jesse’s wife had the same first name – Zerelda – as his mother. Zee, as she was more commonly known, was named after Jesse’s mother. Zee’s mother was Robert James’s sister, making Jesse and Zee James first cousins. The two met in 1865 when Jesse was recuperating from his gunshot wounds in Kansas City. Jesse and Zee had a long engagement, but after nine years, during which time most of Jesse’s energy was spent on the exploits of the James-Younger Gang, the two were married at a family home on April 24, 1874 in Kearney, Missouri. By all accounts a plain woman, Edwards portrayed her in the press as a God-fearing Christian of striking beauty. While that characterization may not have been accurate, there is no doubt that she was loyal to her infamous husband. A year after they were married, Zee gave birth the Jesse, Jr. She had twins on February 28, 1878, but they both died. A year after that, on June 17, 1879, Zee and Jesse welcomed daughter Mary Susan James to the world.

  In June 1871, Jesse and his gang arrived in Croydon, Iowa as many of the town citizens were at a local Methodist church to hear Henry Clay Dean give a speech. Dean was known throughout the region as an entertaining speaker, and he was also an outspoken critic of President Abraham Lincoln. While many in the town were distracted by Dean, the James–Younger Gang stole $6,000 from the Croydon State Bank. Rather than simply taking the money and running, the gang, not wanting to be upstaged by Dean, went to the church and brashly displayed the money they had stolen.

  That crime brought additional attention to Jesse James, and it was an indication that James and his gang were operating across multiple states. In fact, the gang would operate as far south as Texas and as far east as West Virginia. Powerless to stop outlaws like James, banks began turning to the Pinkerton Detective Agency in an attempt to track the
m down. In the 1850s, Allan Pinkerton had established a private detective and security guard agency in Chicago, a forerunner of sorts for both private investigators and the Secret Service. A decade later, the Pinkertons, as the agency was informally called, claimed to have uncovered and thwarted a plan to assassinate President Abraham Lincoln, and from there they created the first secret service in the U.S. during the Civil War. In an effort to fight back against the notorious outlaws that targeted the nation’s railroad system, railroad companies such as Union Pacific hired the Pinkertons to join forces with their own police force to capture the outlaws that preyed on their trains. Now the banks were getting in on the act and hiring the Pinkertons to protect them as well.

  Allan Pinkerton

  Allan Pinkerton’s son Robert was sent to Missouri to find Jesse and Frank, and with the assistance of a local sheriff, Robert Pinkerton tracked the gang to a farm in rural Missouri. However, the gang got away and a few weeks later, Jesse sent another letter to the local press, again claiming that he was an innocent victim.

  The following year, Jesse’s gang rolled into Columbia, Kentucky, intent on robbing a bank. When the cashier, R.A.C. Martin refused to open the safe, one of the bandits turned to leave, then turned back around and shot the man in cold blood. Later that year, Jesse and two of the Younger brothers went to the Second Annual Kansas City Industrial Exposition. In front of thousands of witnesses, they robbed a ticket booth and got away with about $900, but a little girl was shot in the fight with the ticket seller. Jesse again wrote a letter to the paper, denying any involvement by him or the Youngers in harming the child. However, Cole Younger was furious that his name was being mentioned in print in any capacity with the crime. Edwards seized the opportunity to write an editorial titled “The Chivalry of Crime” and compared the bandits to President Ulysses S. Grant, the former Union general. Edwards said that Grant had stolen millions of dollars from Americans, whereas Jesse and his gang stole from the rich to give to the poor.