The former Dalton Gang member was fortunate to miss the fiasco at Coffeyville, Kansas, but now his new bank-robbing gang faced the wrath and bullets of a Missouri town’s stirred-up citizens.

When Bill Doolin and his gang robbed the bank in Southwest City, Missouri, on May 10, 1894, almost 100 shots rang out across Main Street in a shootout between the outlaws and the town’s citizens. The wild exchange of lead threatened to turn the escapade into a reenactment of the fiasco at Coffeyville, Kansas, a year and a half earlier when four members of the Dalton Gang and four citizens were killed and a fifth outlaw seriously wounded during a holdup attempt. The outcome of the earlier venture might have been weighing heavily on Doolin’s mind as he and his comrades in crime tried to get the best of the brave defenders of Southwest City.

Doolin was born in Johnson County, Ark., in 1858, and grew up there. In 1881 he drifted west, and, for the next decade, he worked on ranches in Kansas and Oklahoma Territory and was considered a steady hand. His first brush with the law came around the Fourth of July in 1891 near Coffeyville when he and several other cowboys decided to celebrate the holiday by throwing a beer party. Kansas was a dry state at the time, and when local constables showed up to try to confiscate the refreshments, a shootout ensued, leaving two lawmen wounded. Soon afterward, Doolin joined the Dalton Gang.

However, for some reason, Doolin missed the debacle at Coffeyville in October 1892 when the gang was virtually wiped out. One story says he sensed trouble and, feigning a thrown shoe on his horse, backed out of participating in the robbery at the last minute. Another story claims Doolin was the mysterious “sixth rider” who, according to legend, held the gang’s horses in an alley during the holdup attempt and managed to escape after the robbery went awry.

For whatever reason, Doolin came out of the Coffeyville disaster unscathed and emerged as leader of the gang. He formed the few remaining members, along with new recruits, into his own band, called the Wild Bunch (not to be confused with Butch Cassidy’s later Wild Bunch). Members of the gang probably included Bill Dalton, the last of the outlaw Dalton brothers, and other colorful characters like George “Bitter Creek” Newcomb, Bill “Tulsa Jack” Blake, Charlie “Black Face” Pierce, George “Red Buck” Weightman, Richard “Dynamite Dick” Clifton, Richard “Little Dick” West and William “Little Bill” Raidler. During the next year and a half, the gang robbed several banks and trains throughout Kansas, Indian Territory and Oklahoma Territory and got involved in a number of shootouts with law officers, including the infamous gunfight at Ingalls in Oklahoma Territory on September 1, 1893.

Slightly over eight months later, on May 10, 1894, seven members of the gang rode into Southwest City (sometimes seen as “South West City”), located in the extreme southwest corner of Missouri, at about 3:30 in the afternoon. The masked and heavily armed men rode in from the south and approached Main Street without making any demonstration until they got to the post office on the southwest corner of Main and Cherokee, where they dismounted and tied their horses. Punctuating their language with spectacular oaths, they told everyone on the street to “hunt holes.” To give the command added force, they fired off a volley of warning shots from their Winchesters. The outlaws then kept up a sporadic fusillade as three of them started on foot up Main Street for the nearby bank of A.F. Ault. Two of the other gang members remained behind to watch the horses in the yard of a Dr. Nichols’ office/residence, directly behind (west of) the post office. The last two outlaws took up lookout positions in a pool hall at the northwest corner of Main and Cherokee; the bank was just to the north of the pool hall on the west side of Main. (Bailey C. Hanes’ 1968 biography of Doolin identifies the three men who entered the bank as Doolin, Dalton and Newcomb. Although Doolin probably did enter the bank, most recent authors agree that Dalton and Newcomb were not even present at Southwest City.)

The trio inside the bank quickly got the drop on Ault and his assistant, a Mr. Snyder, while those outside continued firing at anyone who dared to show his head. Two of the men inside jumped onto the counter and crawled through the cashier’s window, while the third covered the bankers with his revolver, forcing them to put their hands over their heads and face the wall. The first two rifled through the cashier’s drawer and ransacked the vault, filling a sack with all the money they could find, which came to about $3,700. In their haste, they overlooked another $5,000 in bank notes that was bound in several packages. After less than 10 minutes inside the bank, the three robbers started back toward their horses on Dr. Nichols’ lawn, marching the two bankers in front of them as hostages.

Meanwhile, the alarm had been raised among citizens, and some of them had secured arms and started returning fire, while others still scurried about helter-skelter. A former state senator, J.C. Seabourn, and his brother Oscar were among the men on the street. Both were struck by shots, in nearly the same place above the right hip, as they started to duck inside a hardware store. (One account of this incident says that a single pistol shot fired by Little Dick West struck both brothers, passing through Oscar’s lower body and lodging in Senator Seabourn’s abdomen. This embellished version is contradicted, though, by newspaper reports at the time, which suggest the two men were struck by separate bullets and that Oscar was the one who had the bullet lodged in him.) J.C. Seabourn died of his wound four days later, while his brother eventually recovered. Another citizen, M.V. Hembree, received a ball in the ankle that almost severed his leg, as he sought shelter inside Barker’s Saloon. One witness said nearly 100 shots were fired on Main Street during the robbery and that it “sounded like war times.”

When the gang members reached their horses, they released the hostages, then commenced firing in every direction and “tore down the street toward the Territory border at breakneck speed.” As they turned south on Broadway, they encountered a determined resistance from several townspeople, including Deputy U.S. Marshal Simpson Melton and City Marshal Carlyle, who had gathered on both sides of the road to give them “a warm reception.” In the exchange of shots, at least two gang members were wounded, including Doolin, who was peppered with buckshot on the side of his head but managed to stay in the saddle.

One of the gang’s horses was also hit, and Melton received a flesh wound in the leg. Continuing their retreat, the outlaws came to the residence of a man named J.D. Powell, who opened fire on them as they rode by, wounding another of their horses. Two other citizens, Charles Franks and Dick Prather, also “gave them a dose” as the outlaws passed the local Baptist Church. On the outskirts of Southwest City, the gang waylaid two citizens driving wagons and cut a horse from each rig to replace the mounts that had been injured while running the gantlet on Broadway Street. One of the new animals, though, wasn’t fast enough to suit the outlaws; so they turned it loose and stole another from a nearby farmhouse. (Although Doolin’s favorite horse, Old Dick, was among those wounded, it was not disabled enough to abandon. Doolin finally sold the animal, however, to a doctor in Ingalls, because its injury had left it no longer valuable as a saddle horse.)

A few miles outside town, the outlaws stopped another team driven by Jim Van Hooser, who was escorting his sister, a Mrs. Sharpe, from his home in Indian Territory by way of Southwest City to her home in Siloam Springs, Ark. Van Hooser balked when gang members first demanded one of his horses, but they raised their Winchesters and, according to one account, “soon convinced him that they wanted the horse badly.”

Several hours after the bank robbery, a posse from Southwest City finally organized and started in pursuit of the bandits, tracking them in a southwesterly direction into Indian Territory (present-day Oklahoma), also known as the Indian Nation or simply the Nation. The outlaws stopped for supper that evening about 12 or 14 miles below Southwest City and also dressed their wounds. The woman who prepared the meal for them said later that six of the seven gang members were injured. The posse, however, failed to catch up with the outlaws and finally lost track of them some distance below the Grand River (also known as the Neosho River). About a week later, one newspaper reported that the robbers had not been heard from, and “the probabilities are they never will be.”

Various parties were suspected of participating in the Southwest City bank holdup, and a reward of $1,700 was offered for the capture of the robbers. One newspaper speculated in the immediate aftermath of the caper that it had no doubt been carried out by “the Starr and Dalton gang, which for years has had a rendezvous in the rough hills not more than thirty or forty miles southwest of Southwest City.” Mrs. Sharpe claimed to have recognized several men whom she knew to be associated with the Henry Starr gang as being among the seven who had waylaid her and her brother outside Southwest City on the day of the robbery. At least two of the men she named, Alf Chaney and Dr. Charles Wynn, had been strongly implicated in helping Starr rob the Bentonville Bank in Arkansas on June 5, 1893. However, at the time of the Southwest City Bank holdup, Alf Chaney was already in jail for his part in the Starr gang’s May 1893 train robbery at Pryor Creek in Indian Territory, a circumstance that casts doubt on Mrs. Sharpe’s entire testimony.

On the other hand, evidence exists to suggest that Dr. Wynn, a known associate and abettor of out- laws, was indeed involved in the Southwest City robbery. Hanes says in his biography that the Doolin Gang spent the night at Wynn’s home at Fairland, Indian Territory, on the evening before the Southwest City holdup, that the doctor cased the town for the outlaws before they entered it, and that they returned to his home after the escapade to have their wounds treated. Although contemporaneous newspaper reports cast doubt on the latter assertion (because they say the robbers were trailed in a southwesterly direction, while Fairland lies considerably northwest of Southwest City), Wynn was, in fact, widely suspected of having aided in the robbery. He and a man named Sparks were quickly arrested, but Sparks was soon discharged for lack of evidence. Wynn was held in jail until the next term of court, at which time he, too, was released when the grand jury failed to bring an indictment against him. A third man, James Condry, was later arrested in connection with the robbery and indicted, but his case never went to trial because of lack of evidence.

Other men identified by Mrs. Sharpe as being among the ones who stole the horse from her brother outside Southwest City or who were otherwise suspected of participating in the robbery included Henry Roberts, Bill Cornett, Tom Crather and Bill Doolin. Although most of these men were apparently not involved in the robbery, they were all considered desperate characters, and Crather was shortly afterward killed on the Grand River in Indian Territory by a posse of 50 men sent out in response to the crime.

Of the suspects identified in the days immediately following the Southwest City Bank robbery, apparently only Doolin was an active participant. In reference to the robbery, the 1897 Illustrated History of McDonald County concluded, “In the course of time, it was demonstrated to the satisfaction of most of the people of the town that the raid had been made by Bill Doolin and his gang.” Most modern sources suggest that the other members of the gang, besides Doolin, who made the jaunt to Southwest City were Blake, Clifton, Pierce, Raidler, Weightman and West.

The Doolin Gang continued to rob and raid throughout Kansas and Oklahoma Territory during the next year and a half. Then, in January 1896, legendary Deputy U.S. Marshal Bill Tilghman finally caught up with Bill Doolin in Eureka Springs, Ark., where the outlaw had gone to seek treatment for a rheumatic leg he’d developed from being shot in the foot during a train robbery near Cimarron, Kan., in June 1893. Tilghman found Doolin in a bathhouse, where he had registered under the alias of Tom Wilson, and arrested him without incident. The hombre was taken back to Guthrie in Oklahoma Territory and placed in jail, but less than six months later he and about 10 other prisoners escaped. In late August 1896, a month and a half after the jail break, Doolin was killed in a shootout with Deputy U.S. Marshal Heck Thomas and members of his posse near Lawson, Oklahoma Territory.

A hundred and some years later, Bill Doolin, like so many outlaws of his era, has become an almost mythical figure, and he has even been romanticized in movies and song. Randolph Scott, for example, played Bill Doolin in the 1949 release Doolins of Oklahoma, and the Eagles’ Desperado album, released in the early 1970s, was inspired by the story of the Doolin and Dalton gangs. The people of Southwest City no doubt would have sung a different song in 1894. To them, there was nothing romantic about Bill Doolin and his notorious Wild Bunch.


Frequent contributor Larry Wood writes from Joplin, Mo. Suggested for further reading: Bill Doolin: Outlaw O.T, by Bailey C. Hanes.

Originally published in the April 2007 issue of Wild West. To subscribe, click here