In September 1873, he went to Dallas, Texas, where he opened a dental office at 56 Elm Street, about four blocks east of the site of today's Dealey Plaza. He soon began gambling and realized this was a more profitable source of income, since patients feared going to his office because of his ongoing cough. On May 12, 1874, Holliday and 12 others were indicted in Dallas for illegal gambling. He was arrested in Dallas in January 1875 after trading gunfire with a saloon-keeper, but no one was injured and he was found not guilty. He moved his offices to Denison, Texas, and after being found guilty of, and fined for, "gaming" in Dallas, he decided to leave the state.
In the years that followed, Holliday had many more such disagreements, fueled by a hot temper and an attitude that death by gun or knife was better than by tuberculosis. The alcohol Holliday used to control his cough may also have contributed. He would regularly use the term; "I'll be your Huckleberry." This may have been merely slang of the period for "I'm your best gun/man." Further, there was the practical matter that a professional gambler, working on his own at the edge of the law, had to be able to back up disputed points of play with at least a threat of force. Holliday continued traveling on the western mining frontier, where gambling was most likely to be lucrative and legal. Holliday was in Denver, Cheyenne, and Deadwood (site of the gold rush in the Dakota Territory) in the fall of 1876.
By 1877, Holliday was in Fort Griffin, Texas, where Wyatt Earp first met him (per his later account). They were initially introduced through mutual friend John Shanssey. The two began to form an unlikely friendship; Earp more even-tempered and controlled, Holliday more hot-headed and impulsive. This friendship was cemented in 1878 in Dodge City, Kansas, when Holliday defended Earp in a saloon against a handful of cowboys out to kill Wyatt, and where both Earp and Holliday had traveled to make money gambling with the cowboys who drove cattle from Texas. Holliday was still practicing dentistry on the side from his rooms in Dodge City, as indicated in an 1878 Dodge newspaper advertisement (he promised money back for less than complete customer satisfaction), but this is the last known time he attempted to practice. In an interview printed in a newspaper later in his life, he said that he only practiced dentistry "for about 5 years."
Holliday also met Mary Katharine Horony ("Big Nose Kate") in Fort Griffin and began his long-time involvement with her. Horony also met Wyatt Earp there. Holliday once stated he considered Horony to be his intellectual equal.
Dedicated gambler, gunman reputation
An incident in September 1878 had Earp, at the time a deputy city marshal, surrounded by men who had "the drop" on him. Holliday, who currently owned a bar in the town and was dealing faro (as he did throughout his life), left the bar, approached from another angle to cover the group with a gun, and either shot or threatened to shoot one of these men. Earp afterward always credited Holliday with saving his life that day. Many other accounts of Holliday's involvement in gunfights, however, are sometimes exaggerated. He had several documented saloon altercations involving small shootings, where he was accounted as fast as Wild Bill Hickok.
One documented instance happened when Holliday was employed during a railroad dispute. On July 19, 1879, Holliday and noted gunman John Joshua Webb were seated in a saloon in Las Vegas, New Mexico when a former U.S. Army scout named Mike Gordon began yelling loudly at one of the saloon girls. When Gordon stormed from the saloon, Holliday followed him. Gordon produced his pistol and fired one shot, missing. Holliday immediately drew his gun and killed Gordon. Holliday was placed on trial for the shooting but was acquitted, mostly based on the testimony of Webb.
Tombstone, Arizona Territory
Dodge was not a frontier town for long; by 1879, it had become too respectable for the kinds of people who had seen it through its early days. For many, it was time to move on to places not yet reached by the civilizing railroad, places where money was to be made. Holliday, by this time, was as well known for his prowess as a gunfighter as for his gambling, though the latter was his trade and the former simply a reputation. Through his friendship with Wyatt and the other Earp brothers, especially Morgan and Virgil, Holliday made his way to the silver-mining boom town of Tombstone, Arizona Territory, in September 1880. The Earps had been there since December 1879. Some accounts state the Earps sent for Holliday when they realized the problems they faced in their feud with the Cowboy faction. In Tombstone, Holliday quickly became embroiled in the local politics and violence that led up to the famous Gunfight at the O.K. Corral in October 1881.
The gunfight happened in front of, and next to, Fly's boarding house and picture studio, where Holliday had a room, the day after a late-night argument between Holliday and Ike Clanton. The Clantons and McLaurys collected in the space between the boarding house, and the house west of it, before being confronted by the Earps. Holliday likely thought they were there specifically to assassinate him.
It is known Holliday carried Virgil's Coach Gun into the fight; he was given the weapon just before the fight by Wyatt Earp, as Holliday was wearing a long coat which could conceal it. Virgil Earp took Holliday's walking stick: by not going conspicuously armed, Virgil was seeking to avoid panic in the citizenry of Tombstone, and in the Clantons and McLaurys.
The strategy failed: while Virgil held up the cane, one witness saw a man, almost certainly Holliday, poke a Cowboy in the chest with a "large bronze pistol" (probably the shotgun), then step back. Wyatt Earp and Tom McLaury were the first men to fire, almost at the same time according to Wyatt's testimony. Shortly after, Holliday used the shotgun to kill Tom McLaury, the only man to sustain shotgun wounds — a fatal buckshot charge to the chest. This probably happened quite early in the fight, before Holliday fired a pistol, though scenarios in which Holliday held a pistol with one hand and a double-barreled shotgun in the other during the gunfight are postulated.
An inquest and arraignment hearing determined the gunfight was not a criminal act on the part of Holliday and the Earps. The situation in Tombstone soon grew worse when Virgil Earp was ambushed and permanently injured in December 1881. Then Morgan Earp was ambushed and killed in March 1882. After Morgan's murder, the Earps, their families, and Holliday fled town. In Tucson, while Wyatt, Warren Earp, and Holliday were escorting the wounded Virgil Earp and his wife Allie to California, they prevented another ambush and this could have been the possible start of the vendetta against Morgan's killers.
Earp Vendetta Ride
The first victim of the vendetta was Frank Stilwell, a former deputy of Johnny Behan's. Stilwell was in Tucson to answer a stage-robbery charge but wound up dead on the tracks in the train yard near the Earps' train. What Stilwell was doing in the train yard has never been explained (he may have been waiting to pick up another man who was supposed to testify in his favor), but Wyatt Earp certainly thought Stilwell was there to do the Earps harm. In his biographies, Wyatt admitted to shooting Stilwell with a shotgun. However, Stilwell was found with two shotgun wounds and three bullet wounds. Holliday, who was with Wyatt that night and said Stilwell and Ike Clanton were waiting in the train yard to assassinate Virgil Earp, is likely the second shooter. Holliday never directly acknowledged his role in Stilwell's killing or those that followed.
After the Earp families left for California and safety, Holliday, Wyatt, Wyatt's younger brother, Warren, and Wyatt's friends Sherman McMasters, Turkey Creek Jack Johnson, and Texas Jack Vermillion rode on a vendetta for three weeks, during which Curly Bill Brocius and at least two other men thought to be responsible for Morgan's death were killed. Eventually, with warrants out for six of the vendetta posse (including Holliday) in the Arizona Territory for the killing of Stilwell, the group moved to New Mexico, then Colorado, in mid-April 1882. While in New Mexico, Wyatt Earp and Holliday had a minor argument and parted ways, going separately to different parts of Colorado.
After the vendetta ride, neither Holliday nor any other member of the party ever returned to Arizona to live. In May 1882, Holliday was arrested in Denver for the Stilwell killing. Due to lack of evidence, Colorado refused to extradite him, although he spent the last two weeks of that month in jail while the issue was decided. He and Wyatt met again in June 1882 in Gunnison after he was released. There is controversy regarding whether any of the Earp vendetta posse slipped briefly back to the Tombstone area to kill Johnny Ringo on July 13, 1882. Biographers of Ringo do not believe it is very likely. Several other known gunmen were also implicated in the death, including "Buckskin" Frank Leslie, little known gunman Lou Cooley, and gambler Mike O'Rourke. Some believe, however, that Ringo's death was in fact a suicide, as reported.
Final illness and burial
Holliday spent the rest of his life in Colorado. After a stay in Leadville, he suffered from the effects of the high altitude; as a result of this and his increasing dependence on alcohol and laudanum, often taken by consumptives to ease their symptoms, his health, and evidently his gambling skills, began to deteriorate.
In 1887, prematurely gray and badly ailing, Holliday made his way to the Hotel Glenwood near the hot springs of Glenwood Springs, Colorado. He hoped to take advantage of the reputed curative power of the waters, but the sulfurous fumes from the spring may have done his lungs more harm than good. As he lay dying, Holliday allegedly asked for a drink of whiskey. Amused, he looked at his bootless feet as he died — no one ever thought that he would die in bed, with his boots off. His reputed last words were, "Well I'll Be Damned. This is funny." Recent Holliday biographer Gary L. Roberts, however, considers it unlikely that Holliday, who had scarcely left his bed for two months, would have been able to speak coherently, if at all, on the day he died. Despite legend, Wyatt Earp was certainly not present when Holliday died, and did not know of his death until months afterward. Though she later attested to attending him in his final days, it is also highly doubtful that Big Nose Kate was present at his death.
An Episcopalian minister presided at Holliday's burial, which was on the day of his death, Nov. 8, 1887. His grave stone sits in Linwood cemetery, which overlooks Glenwood Springs. Entirely on the basis of the late date in the year, it has been speculated (for example) that he was not actually buried in his marked grave, or even in the cemetery itself, on the theory that the ground was frozen and he must have been buried the same day in what was probably a temporary grave, not in the old cemetery, which was up a difficult road on the mountain. However, the weather was evidently mild at the time of Holliday's burial, as biographer Gary Roberts has located evidence of other bodies being transported up the mountain to the same cemetary at the same time in 1887. Roberts argues that it is thus possible Holliday's body is indeed where the modern gravesite is, but no exhumation has been attempted.