Major S.A. Doran’s gang ambushed Frank ‘Boss Gambler’ Flynn and two of his brothers in February 1884, triggering an exchange as deadly as the Gunfight at the O.K. Corral.

Most people who traveled to Hot Springs, Arkansas, in the 1880s did so to soak in the mineral baths in hopes of improving their physical health. Not so Samuel Alexander Doran, native Kentuckian and ex-Confederate major. In late fall 1883 Doran, who seldom visited a place without having some kind of confrontation (often deadly), was en route from New Orleans to the spa town in the Ouachita Mountains in hopes of improving his financial health.

A dishonest gambler willing to back his card play with gunplay, Doran had broken the law in a string of towns from Kentucky to Texas. He had left more than a few places on bad terms and was lucky to have spent relatively little time behind bars. It was in New Orleans that Doran had met Jim Lane. Lane had owned and operated two Hot Springs saloons and gaming establishments—the Monarch and the Palace —until running afoul of Frank “Boss Gambler” Flynn. Lane had asked Doran to come to the “Spa City” and stand up to the powerful Flynn gang. It was an offer the New Orleans gambler could not refuse—not for a payment of $6,000.

Born in 1839, S.A. Doran, known to friends as “Alex,” had two brothers and sisters. His family owned and operated a mercantile store in Louisville. By the outset of the Civil War he seemed destined to a successful career as a merchant. Doran’s sympathies were with the Confederacy, and at age 22 he joined fellow Kentuckian John C. Breckenridge (former vice president to President James Buchanan), who had resigned his U.S. Senate seat to raise a regiment. Doran fought alongside Breckenridge’s troops at Shiloh, Murfreesboro and Chickamauga, rising to the rank of major.

Back in Kentucky after the war. Doran found the mercantile business boring. He had developed a fondness for gambling, drinking, chasing women and fighting (not necessarily in that order) that would stick with him the rest of his life. He got into gambling quarrels and other scrapes, during which he shot three men. He was charged and tried but in each case claimed self-defense and escaped prosecution. The major moved to Atlanta, but after arguing with and then wounding a prominent businessman, he bolted to Memphis. Two Atlanta officers followed him. When they could not persuade Tennessee’s governor to sign the extradition papers, they concocted a scheme to kidnap Doran and haul him back to Georgia. Learning of their plan, Doran “placed a card” in the Memphis Avalanche warning that if the duo “made any attempt to capture him, he would kill both of them.” The Georgia officers returned home empty-handed.

Soon after, Doran fell behind on his rent, and his landlord, Colonel Francis E. Whitfield, and Whitfield’s younger brother Edwin threatened to evict and embarrass him. Once again Doran took out a card in the Avalanche, this time denouncing the Whitfields and warning them not to harass him. Two days later Edwin and two other men showed up at the apartment while Doran was in bed with what the Memphis newspapers described as “two lewd women.” Doran admitted only young Whitfield and then pulled a gun from under his pillow and shot him three times, once through the heart. This time Doran did stand trial for murder, but after 27 days of testimony the jury declared him not guilty by reason of self-defense. Doran had brought a gun to court, and he was ready to use it when two members of the disappointed Whitfield family confronted him, but Doran’s attorney, Casey Young, prevented bloodshed and then persuaded his client it was best to leave Memphis behind.

In the mid-1870s Doran appeared west of the Mississippi at Malvern, Ark., a new town southwest of Little Rock at the junction of the Iron Mountain Railroad and the El Paso stage line to Hot Springs. People en route to the spa in the Ouachita Mountains generally had a layover in Malvern while awaiting the stage to Hot Springs, 25 miles to the west. Aware that travelers to the spa typically carried enough funds to support themselves for weeks, Doran and partners James Sherman and Lucius McCann saw opportunity and ran crooked gambling games (dice, three-card Monte, etc.) in Malvern.

Fleeced travelers, as well as Malvern citizens concerned about their town’s reputation, asked Arkansas Governor Augustus Hill Garland to look into the exploits of Doran and associates. Garland at first paid little attention to the complainers. But then he heard from Little Rock residents Johnny Maree and Jack Curtis, who claimed that when they tried to help a friend recover the $150 he had lost to Doran, the gambler drew a pair of revolvers and announced if they“had come to fight, they could have it.” Two of the major’s employees stood by armed with shotguns, and the Little Rock men quickly retreated. Responding to the men’s complaint, Garland called on his troubleshooter, General Robert C. Newton of the state militia, instructing him to clean out “that gang of fakirs” no matter how much force it took.

Newton, an ex-Confederate officer, and two other men—General J.B. Bull and Little Rock detective Gabe Jones —went to Malvern in March 1875 and told Doran and his gang to leave town. “I don’t see how you can compel us to leave,” Doran said. Newton had an answer prepared: “In this instance I represent the state of Arkansas, and the question of your remaining turns on whether you can successfully defy the whole military and civil power of the state government, which will be invoked if necessary, and if you and your gang are still in Malvern 24 hours from now.” Newton reminded Doran that a wire to the governor would bring 100 armed militiamen. Doran grimaced, but then smiled and bowed. “General,” he said, “you’re too strong for me. I’ll go in the required time.”

Later that year the gang transferred its illegal gambling operations to Hearn, a volatile little town in east Texas. Doran quickly found trouble and killed two men in a card game. Once again he was successful in pleading self-defense. Doran next went to Denison, just south of the Red River and the Oklahoma Territory border. There, in a drunken altercation, he killed police officer “Red” Patman and seriously wounded officer Barney Daniel. Authorities charged the major with murder and attempted murder, jailed him and denied him bail. For more than a year Doran languished while his brother spent in excess of $10,000 in attempts to free him. When the prosecution’s key eyewitness vanished in 1879, authorities were forced to dismiss the charges against Doran, and they ordered him out of town.

In the early 1880s Doran showed up for a short while in Shreveport, La., where he again engaged in a drunken fracas that resulted in bloodshed. Yet again his luck held, as authorities allowed him to leave the Red River port. Doran then went to New Orleans. Jim Lane ventured to the Crescent City to look up the major, as he knew he wasn’t going to best mighty Arkansas operator Frank Flynn without a serious fight. If nothing else, S.A. Doran was a fighter.

Flynn had been in Hot Springs for some 10 years and through bribes and payoffs to city officials had reached a position of power. From his saloon, the Office, he dictated final unwritten authority over who could or could not operate a gambling establishment in the spa town. Flynn and Lane had been partners at one time but had come to a parting of the ways. When Lane opened the Palace and the Monarch without Flynn’s blessing, the Boss Gambler and his hirelings entered Lane’s establishments, overturned the gambling tables and closed them—all while police looked the other way.

Lane had returned to his New York home to lick his wounds, seething with hatred for Flynn and planning revenge. His wife, Gracie, a prominent brothel madam, had remained in Hot Springs and updated him about goings-on in town. Other local businessmen shared Lane’s dislike for Flynn. Several of them gave Lane $6,000 to hire someone to either run the Boss Gambler out of town or kill him.

Lane knew S.A. Doran by reputation only when he sought him out in New Orleans in fall 1883. He was likely impressed at first sight, as most people were. The 40-year-old major stood 6- foot-3 and weighed 220 pounds, with broad square shoulders and a dark brown beard speckled with gray. Although he had a ramrod military bearing and his voice could sound gruff, Doran could also be friendly and show charming manners. Lane’s offer to stake Doran for his services could not have come at a better time. Doran still owed his brother $10,000 for attorney’s fees incurred at Sherman, Texas, and he had been down on his luck of late. Also looking forward to a change of scenery, Doran told Lane he would leave for Hot Springs within the week.

When S.A. Doran arrived at Hot Springs in early December 1883, he was not alone. He’d brought with him Dave and Bob Pruitt, known gamblers from Mississippi who had each killed men in gunfights. The trio set about to reopen Jim Lane’s Monarch and Palace saloons and gambling halls. Frank Flynn got wind of it and approached Doran, whom he’d met years before in east Texas. Aware of the major’s reputation as a tough and fearless gunman, Flynn sought to buy him off. Drop the idea of opening Lane’s houses, Flynn told Doran, and he would stake Doran in any Hot Springs business venture of his choosing. To Flynn’s surprise, Doran refused, saying he had given Lane his word and was bound by that oath.

Flynn, no stranger to violence himself, believed he had no alternative but to prepare for battle with Doran. Ten years earlier the Boss Gambler had killed a man in Austin, Texas, and in a Hot Springs bar in 1876 he had shot and killed ex–Deputy Sheriff James Kinnehan. In downtown Hot Springs on September 22, 1882, just over a year before Doran’s arrival, Flynn had shot and killed Charles Matthews, editor of The Daily Hornet. But pitted against Doran, Flynn knew he needed help, so he sent for his brothers, Billy and Jack, and summoned three gun hands from Texas—Hugh Behan, Jimmie Freehan and “Doc” Nagle.

Doran in turn realized he needed more help than just the Pruitt brothers. For additional firepower he brought in Harry Lansing, Jake Lucius, Ed Howell, John Allison and O.R. Ellison, each of whom had a history of violence. The little mountain town was rapidly becoming a dangerous place, and the arrival of all these toughs alerted the citizens of Hot Springs that the trouble between the opposing gambling factions could explode at any time.

The Palace Saloon and gam- bling hall reopened amid great fanfare on December 13, 1883, with a band playing lively tunes and the staff serving great quantities of food to a large crowd. But customers couldn’t help but notice the shotguns and rifles leaning against the wall at each gambling table, and many stayed away after opening night. The tension was also palpable in Flynn’s Office Saloon. The first shots, though, came not in one of the saloons but on Central Avenue, the main thoroughfare in Hot Springs.

Flynn had sent a challenge to Doran, suggesting the two of them settle their differences “one-on-one.” The major immediately went looking for the Boss Gambler. On December 17, in an encounter the Arkansas Gazette billed as A BLOODLESS DUEL, the antagonists met in downtown Hot Springs. Doran pulled his gun first and got off three shots to Flynn’s one. Witnesses claimed they saw puffs of dust rise from Flynn’s coat, and it was assumed he wore a coat of mail for protection. Even so, Flynn was said by some to be “spitting blood” for a couple of days afterward. Doran was unhurt.

Hot Springs authorities charged Flynn with carrying a pistol and disturbing the peace. They charged Doran and the Pruitts with illegally operating a gambling house. But the matter between the men was hardly closed.

Flynn had no illusions about Doran —clearly the major intended to kill him or run him out of town. The Boss Gambler decided to kill him first. Aware that Doran took his lunch and dinner every day at the Arlington Hotel, almost directly across the street from the Palace Saloon, Flynn and two of his gunmen rented a second-floor front room at the hotel and set up a sniper’s nest with two Winchester rifles and a shotgun. But the plan went awry when Doran became suspicious and failed to show. Flynn later denied a maid entry to their room, and she reported the incident to hotel manager S.H. Stitt. When Stitt checked and discovered the heavily armed trio, he ordered them to leave the hotel, threatening to summon Police Chief Tom Toler. Word spread rapidly of the attempted ambush, and public opinion, which had been heavily in favor of Flynn following the “bloodless duel,” now switched in favor of Doran.

Jim Lane suddenly appeared in Hot Springs with a plan. He pointed out to Doran that the gambling houses were losing money because people were keeping away, afraid a gunfight might break out at any moment. Lane proposed the two of them create the appearance they were selling out and leaving town. If Flynn believed they had given up, he might allow someone else to operate the clubs and relax his guard. Doran could then slip back into town and complete his mission—to rid Hot Springs of Frank Flynn.

Lane issued a paper transfer of the Palace title to Dave Pruitt, and Lane and Doran left town, the latter returning to New Orleans. A justly suspicious Flynn had a friend of his in New Orleans keep an eye on the major and after a couple of weeks was nearly convinced Doran and Lane would stay out of his hair. On February 3, 1884, however, Flynn’s friend informed him by telegram that Doran had just hopped an Arkansas-bound train. The Boss Gambler quickly assembled six of his gun hands, and he and the heavily armed men left town in two buggies. At Lawrence Station they boarded an eastbound train on the “Diamond Jo” Line. Arriving at Malvern, the transfer point for Doran’s train, the men learned that the major’s train was running late. Flynn placed one of his men on a train to Arkadelphia (25 miles southwest), instructing him to board the northbound train and find out which coach Doran was in so he could point it out once the train reached Malvern. Fortunately for Doran, a friend of his (believed to be Tom Shannon, owner of the Owl Saloon) had spied Flynn and his men slipping out of Hot Springs and correctly guessed their bad intention. A telegram, signed T.S. and sent to Doran in care of the station at Prescott, Ark., read, YOU MAY WANT TO AVOID PLANNED RECEPTION AT MALVERN. Doran experienced another stroke of good luck as he left the train at Arkadelphia—the man Flynn had dispatched to intercept the major failed to see him.

Flynn and his men vainly searched the train at Malvern, trying to figure out what had happened to Doran. The major, meanwhile, had hired a buggy in Arkadelphia to take him through the mountains to Hot Springs—unseen by any of the Flynn faction. Boss Gambler’s plans to ambush his adversary had failed. Now it was Major Doran’s turn to plan a surprise attack.

On the dreary morning of February 9, 1884, Doran sprang his trap. Frank Flynn and brothers Billy and Jack left the Office about 10:30 in a closed hack owned and driven by Frank Hall. They were headed home after a busy night at the saloon. A witness later claimed that as the hack pulled into the street, an unidentified caller, using an old crank telephone, called the Doran party at the Owl Saloon and merely said, “They are on their way.”

A slow drizzle was turning the street surface to mud. Several dozen people strolled the sidewalks, many headed to their hotels or homes after their prescribed morning mineral baths. Hall urged his big bay into a lively trot as the hack rolled south on Central Avenue. Inside the hack, behind its closed side curtains, Frank and Billy Flynn were on the rear seat facing forward. Their brother Jack was on the front seat facing them. All three were heavily armed—Billy and Jack with shotguns, Frank with a Winchester rifle.

As the hack passed the Owl, on the west side of the street, seven men filled the double doors and the second-floor gallery. At a signal Doran and his six hired gun hands opened a murderous barrage. Rifle bullets, buckshot and slugs tore through the thin wood and fabric of the hired buggy (witnesses later counted more than 140 bullet holes in the body of the hack).

Jack Flynn died instantly as a rifle bullet struck him in the head and buckshot tore through his lungs. Hack driver Frank Hall took a load of buckshot to the upper body, and crumpled from the driver’s seat, mortally wounded. The hack slowly rolled to a stop, just north of the Arkansas National Bank. Frank Flynn, shot in the thigh, realized the thin walls of the hack were of little protection and managed to throw himself to the ground, immediately followed by Billy Flynn. The brothers crouched behind the coach and fired their revolvers at the Doran crowd, who had emerged from the Owl and were openly kneeling and firing their weapons.

J.H. Craig, a pedestrian caught in the crossfire, tried to run to safety but took a load of buckshot to the “upper part of the back and left shoulder.” Bob Hargroves, who was in the Star Barber Shop when the shooting started, curiously stepped onto the sidewalk and caught a rifle ball just below the heart. He would die a few days later.

Billy Flynn emptied his revolver at their assailants and ran for the safety of the bank on the west side of the street. Shot through the chest, he fell at the gutter’s edge. Amazingly, he would recover from his chest wound.

Frank Flynn, too, had run out of pistol ammunition. He reached into the hack, recovered his Winchester, and sprinted for the stairway entrance to the Ozark Club, receiving a bullet wound to one of his hands en route. Reaching the stairwell, the Boss Gambler knelt and, despite his wounded hand, levered shot after shot at the Doran crowd to his north.

The battle raged for several minutes. The Arkansas Gazette reported, “Buckshot, rifle bullets and pistol balls rained up and down the avenue in dangerous and murderous numbers.” The Daily Bulletin estimated that the men fired between 80 and 100 shots and reported that a brownish haze of smoke and the smell of gunpowder hung in the damp downtown air.

Then, suddenly, into the midst of the melee strode Tom Toler, the young chief of police. He was toting a double-barreled shotgun and had a revolver tucked into his belt. In a loud and clear voice he said: “I command you to stop! I’ll kill the next man that fires a shot. Now drop those guns, you are all under arrest.” His tone must have convinced the antagonists, as their weapons at last fell silent. Two officers helped the chief collect weapons and arrest Doran, David and Robert Pruitt, Harry Lansing, Ed Howell, Jake Lucius and John Allison. Toler allowed bystanders to take the severely wounded Billy Flynn to brother Frank’s home for care and had a doctor treat Frank’s wounds. The chief then arrested the Boss Gambler and rounded up his gang.

Visitors to the “Spa City” were appalled by the intense gun- fight that had killed three men and wounded three others on the main thoroughfare. The hail of bullets had shattered windows and pocked storefronts. Hordes of people checked out of the hotels and headed for the train—it was time to “get out of Dodge.” A committee of 12 formed that afternoon, soon backed up by a 70-man armed militia. Their orders were to run every gambler out of town —either peaceably or by force.

Strangely, both the Flynn and Doran gangs pleaded self-defense—more strangely though, juries declared every one of them not guilty by reason of self-defense. Three men were dead, three others wounded (the same number of casualties as occurred at the far more infamous October 1881 Tombstone gunfight down in Arizona Territory), yet no one was guilty. Only at Hot Springs during that era could juries have reached such a verdict. Following trial, members of both gangs quickly scattered.

Billy Flynn was taken to his mother’s home in Little Rock to recover. Just over a month later, on March 11, he tried to kill Robert Pruitt, onetime Doran gang member, outside the upscale Capitol Hotel on Little Rock’s Markham Street. His three shots from a Colt .45 all missed. He was arrested and later tried and convicted of assault to kill.

Brother Frank, head of the Flynn gang, also moved to Little Rock, where for several years he ran a gambling room for resident Angelo Marres. Flynn and family did return to Hot Springs after the turn of the century, but he never regained his position as Boss Gambler. Frank and his wife ultimately separated, and she moved away. He spent his last years suffering from Bright’s disease. His dying request at the Hot Springs Army and Navy Hospital on October 4, 1910, was that his body be interred in the Little Rock National Cemetery and that his wife and daughter not be informed of his death.

Doran gang member Ed Howell remained in the spa town and had a deadly encounter with Chief Tom Toler in September 1884. Hearing of death threats from Howell, Toler shot him down in the Opera House Bar. A coroner’s jury called the killing “justifiable by reason of self-defense.” Toler himself was killed in a March 16, 1899, gunfight on Central Avenue, the climax of a dispute between the Hot Springs Police Department and Garland County Sheriff’s Office (see the feature “Lawmen’s Heated Gun Battle in Hot Springs” in the October 2002 Wild West). Five men were killed that even bloodier day in Hot Springs.

The last member of the rival gambling factions to leave Hot Springs was the major. Doran had hung around the spa town for two years and continued to be a lightning rod for trouble, mainly when he had been drinking. He was accused of stabbing Arthur Parker, a black man, but authorities dropped the charges when Parker and witnesses failed to appear. He was arrested several times, always carrying a pistol. Doran finally got the message he was no longer wanted in Hot Springs. He had been successful in ending Flynn’s rule as Boss Gambler, but in doing so he had injured the gambling fraternity and was forced to find new pastures.

Doran left Hot Springs for good in June 1886, turning up shortly thereafter in Fort Smith, still a frontier town on the border of Indian Territory (present-day Oklahoma). Full of saloons and brothels, it was Doran’s kind of town.

Sure enough, the major soon found more trouble, after stealing prostitute Dot Rowland away from Pink Fagg, described in the newspapers as “an old gambler and transient knight of the green cloths.” Fagg had served several years in the Missouri State Penitentiary for having shot and killed his wife and her young lover, whom he had discovered in a tryst.

Doran and Fagg each frequented the Phoenix and Le Grande saloons and were constantly running into each other. Generally when that happened, an argument ensued, and it was necessary for bartenders to separate the two men to avoid serious trouble. On the evening of July 16, 1887, the tension between the two reached a climax when they crossed paths at Le Grande and argued once again. The argument seemed to peter out, and the two old gamblers actually stood at the bar and had a drink together. Doran announced to the room that he was tired and going home, and Fagg walked out the saloon door with him. As Doran started down the street, Fagg, who would never have faced the major face to face, produced a Smith & Wesson .44 revolver and fired two shots into the back of Major Doran. Doran fell, then rolled up to a sitting position and managed to thumb off a shot from his .44-40 Colt. He missed his target, then fired a second shot, which also missed—Doran, according to an account in the Arkansas Gazette, “evidently being dazed or too much under the influence of liquor.” Fagg emptied his gun, hitting Doran at least one more time. Doran slowly rolled over, mortally wounded.

The major died two days later and was buried at Fort Smith. Fagg was indicted, tried, convicted of murder and sentenced to the Arkansas State Penitentiary at Little Rock. Only a few days before he was shot, Doran told a friend he had killed nine men in his life, had been indicted for murder in the first degree eight times and was never convicted of any of those charges.

An Arkansas Gazette editorial called him a “desperado” and commented, “Doran was a man of blood, who courted deadly encounters, and who at last fitly became the victim of bloodshed. Bloodstains marked his progress. His presence was the signal for strife and turmoil, generally ending in the shedding of blood.” The newspaper also reported how the citizens of Hot Springs felt about Doran’s slaying: “Hundreds of people hereabout breathe easier now that he is dead; not because of personal fear, but for the sake of the fair name of this city, in which the dead chief among gamblers never came without being the precursor of some trouble.” How very true. It was almost a sure bet that anywhere Major Doran ventured, trouble and violence were bound to tag along.


Orval E. Allbritton of Hot Springs, Ark., wrote “Lawmen’s Heated Gun Battle in Hot Springs” in the October 2002 Wild West. For further reading see his books Dangerous Visitors: The Lawless Era and Hot Springs Gunsmoke; the latter includes two chapters that further describe the deadly Flynn-Doran affair.

Originally published in the February 2012 issue of Wild West. To subscribe, click here.