Roy Daugherty

One of the most interesting notorious characters of the Old West era from the Ozarks was Roy "Arkansas Tom" Daugherty; yet he is someone that many people are not familiar with. Actually, Daughterty's criminal career merely started during the Old West era with his participation in the Doolin gang's infamous shootout at Ingalls in Oklahoma Territory in 1893. It continued well into the twentieth century until he was finally killed in a shootout with Joplin police in 1924.
Daugherty was born in Missouri but apparently spent enough time in Arkansas to acquire his colorful nickname before drifting into Oklahoma Territory and hooking up with Doolin. Daugherty was captured at Ingalls, although the rest of the gang escaped. He spent a good while in prison but was paroled in the early 1900s and was even in a movie called Passing of the Oklahoma Outlaws, in which Henry Starr also had a bit part. Daugherty, though, apparently decided that being an outlaw was more fun than playing one in the movies, because he soon resorted to bank robbery, except that now he was using motor vehicles instead of horses as his means of transportation (and escape). He robbed banks at Oronogo, Fairview, and Asbury (all in southwest Missouri) and perhaps other places as well before his encounter in west Joplin with the constabulary of that town proved to be his undoing. After he was killed, his body was taken to a Joplin undertaker, and the next day thousands of spectators filed through the mortuary, anxious to get a glimpse of a man who was one of the last links to the Wild West days of yesteryear.

Eureka Springs Bank Robbery

Henry Starr, as I pointed out last time, was killed in a bank robbery at Harrison, Arkansas, in February of 1921. The rest of the gang escaped, but apparently they didn't learn much from the fatal outcome of the crime. A year and a half later, in September of 1922, the attempted holdup of a bank in Eureka Springs ended even worse for the remnants of the gang than the Harrison caper had. Local citizens armed themselves when they realized a crime was in progress, and three of the gang members were killed and the other two wounded and captured in the ensuing shootout. Commenting on the downfall of the gang, some people have pointed to various mistakes the robbers made, such as the fact that they chose a difficult target with few easy escape routes and the fact that they brought along a raw, inexperienced kid as the driver of the getaway car. There is little doubt that the gang was pretty inept, but the main mistake they made was not taking into account the determined resistance the townspeople put up. As one newspaperman pointed out at the time, maybe they didn't realize they were in Arkansas, and standing idly by while their bank was getting robbed was not how they did things in Arkansas back then.
I recently had an article in The Ozarks Mountaineer about the failed Eureka Springs bank robbery, and you can also read a version of the story in my book about notorious Ozarks incidents, which, by the way, I've finally received a copy of. So, it should be available in bookstores very soon if it isn't already. I thought it was going to be out long before now, but the wheels always turn slowly in the publishing world and sometimes even more slowly than others.

Henry Starr

If a tendency toward violence and crime is inherited or even if one's social environment plays an important role, it is little wonder that Henry Starr, the so-called "King of the Bandits," grew up to become a notorious outlaw. Also sometimes called the "Cherokee Badman," Starr's mixed-race Cherokee family had a long history of violence dating back to the feud that developed between the John Ross faction (mostly purebreds) and the Major Ridge faction (mostly mixed-race Cherokees) over the question of removal of the Indians from their native homelands in the southeastern United States. Henry's great grandfather, James (whose mother was a full-blooded Cherokee and whose father was white) was a member of the Ridge faction, which favored the removal treaty. After the removal to Indian Territory in the late 1830s, bitterness lingered, and open warfare erupted between the two sides during the 1840s. James's son Tom (Henry's grandfather)was suspected of killing several members of the Ross faction, and James was killed in retaliation for his son's actions. Tom then supposedly killed several more pro-Ross Cherokees in revenge for his father's death before a treaty between the two warring factions finally brought the bloodshed to a close, at least until the Civil War. During the war, Tom Starr served with Stand Watie and most of the other other mixed-race Cherokees in the Confederate Army, while many of the purebreds served in the Union. After the war, Tom's son Sam became notorious in his own right and later married Belle Shirley Reed, the widow of outlaw Jim Reed, who became infamous as Belle Starr. Another of Tom's sons, George, was the father of Henry, who went on, according to legend, to carry out more robberies than any other outlaw in American history, beginning during the Old West days of the 1890s and ending in February of 1921 when he was killed trying to rob a bank in Harrison, Arkansas. You can read more about Henry Starr and particularly the Harrison bank robbery in my book about notorious Ozarks incidents.

Cora Hubbard--Female Bandit

After Cora Hubbard helped a couple of male sidekicks hold up the Pineville Bank in the summer of 1897, one area newspaper compared her to Belle Starr, the so-called "Bandit Queen." In actuality, of course, Cora's notoriety never approached that of Belle Starr, but Ms. Hubbard did cause quite a stir in the southwest Missouri region for a brief time, not only for the audacity of her bold act but also for her unrepentant atttitude about the deed she had committed. In fact, she seemed quite proud of having committed the crime and, after being captured, even posed for pictures wearing the men's clothes she had donned for the robbery and holding the rifle she had wielded. A pistol that was recovered from the crooks when they were caught had the initials of one of the Dalton gang carved on its handle, and Cora claimed the weapon belonged to her and that she had been with the Daltons several years earlier. Cora seemed to like the idea of shocking people, but in the end the only thing her unabashed attitude got her was a good long stretch in the Missouri state pen. She was let out after serving about seven years, but what happened to her after that is not known.
I've had articles about Cora Hubbard published in Wild West and The Ozarks Mountaineer, and a version of her story also appears as a chapter in my Ozarks Gunfights book.

The Staffelbachs

Galena, Kansas was founded as a lead mining camp in the late 1870s, and it was a wild and rowdy place during its early days. Several notorious incidents happened in the vicinity during the late 1800s, a couple of which I've already mentioned in previous posts. Perhaps the one that is most famous (or infamous) locally, however, is the murder (or murders) committed by the Staffelbach family in 1897. The Staffelbach home sat near present-day West 7th Street in Galena, and the family consisted of the mother and several grown sons, all of whom were shady characters. The old lady ran a house of ill fame out of her home, and the boys were in and out of trouble for a number of petty crimes. In the summer of 1897, they graduated to murder when two of the sons killed a gentleman caller who came to the house one night in the wee hours of the morning and insisted a bit too strongly upon seeing one of the female occupants of the house. The body was dumped in an abandoned mine shaft not far off 7th Street. After the body was discovered, the Staffelbachs were quickly suspected of the crime, and soon the whole gang was rounded up. At their preliminary hearing and trial, several other crimes came to light of which they were suspected, but they were tried only for the death of the gentleman caller. That was enough. The whole family, including the old lady, were convicted on various counts and given sentences of varying severity. The two sons who had actually commited the deed were given the death sentence but later had the penalty commuted to life imprisonment.

Bill Doolin's Southwest City Bank Robbery

When I wrote about the Daltons' fiasco at Coffeyville last time, I remarked that Bill Doolin has been mentioned as possibly having been the gang's supposed "sixth rider." What is known for sure is that Doolin soon organized the remnants of the Dalton gang into the Wild Bunch (not to be confused with Butch Cassidy's Wild Bunch) and almost reenacted the Dalton disaster when he and the gang held up a bank in Southwest City, Missouri, in May of 1894, a year and a half after the Coffeyville caper. The townspeople of Southwest City opened fire on the outlaws the same way the citizens of Coffeyville had done with the Daltons. The outlaws returned fire, and over a hundred bullets whirred through the air on Main Street in a gun battle that one observer described as akin to war times. The outcome, though, was very different from what happened at Coffeyville. When the shooting stopped, one townsperson lay mortally wounded and a couple of other had lesser injuries, while the robbers had run the gauntlet of the citizens' guns and escaped with about $3,500 in cash and only minor wounds. Bill Doolin was finally captured about a year and a half after the Southwest City robbery. He escaped about six months later but was tracked down and killed by a U. S. deputy marshal only a month or two after his escape.

The Daltons' Coffeyville Fiasco

Although Coffeyville, Kansas, is not actually a part of the Ozarks, it's close enough to my hometown of Joplin that I consider it to be in the general region. So, I've included a chapter on the Dalton gang's unsuccessful attempt to rob two Coffeyville banks simultaneously in my book about notorious incidents of the Ozarks.
The holdup attempt occurred on October 5, 1892. The Daltons had grown up hearing about and idolizing their notorious cousins, the Youngers, and the Youngers' even more infamous sidekicks, the James brothers; and Bob Dalton had supposedly boasted that he meant to top the record of Jesse James. Instead, the whole gang was virtually wiped out by vigilant townspeople who armed themselves when they realized the banks were being robbed and shot the outlaws to pieces. Four of the five gang members were killed, and the fifth was seriously wounded.
The story of the failed holdup attempt has been written about fairly extensively, and one of the elements of the story that continues to fascinate students of the Old West is the question of whether or not there was a so-called "sixth rider," as popular myth holds. This person, so the story goes, acted as a lookout on the outskirts of town and managed to escape when the shooting started, and there has been much speculation about the person's identity, if, indeed, he existed. Some, for instance, have claimed that Bill Doolin was the sixth rider.
Local residents who met the Daltons coming into Coffeyville on that fateful morning reported seeing six men, and their testimony has given rise to over a hunded years' worth of sometimes wild speculation. None of the citizens in town, however, saw more than five men, and Emmett Dalton, the only outlaw who survived the ill-fated holdup attempt, also said the gang numbered only five. I think Emmett was probably telling the truth, but many people love a mystery and will eagerly advance a marvelous explanation while scoffing at a simpler, more logical one.