Born in Salisbury, Missouri, in 1878, Dugan resided in Juneau, Territory of Alaska, after trekking north during the Klondike Gold Rush of 1896–1899 and became a cabaret singer. She subsequently moved to Pima County, Arizona, where she worked for an elderly chicken rancher, Andrew J. Mathis, as a housekeeper. Shortly after her employment was terminated for unknown reasons, Mathis disappeared, as did some of his possessions, his Dodgecoupe automobile and his cash box. Neighbors reported that Dugan had tried to sell some of his possessions before she disappeared as well. The police discovered Dugan had a father in California and a daughter in White Plains, New York. She had been married five times, and all her husbands had disappeared. She sold the Dodge coupe for $600 in Kansas City, Missouri. She was arrested in White Plains when a postal clerk, alerted by the police, intercepted a postcard to her from her father in California. She was extradited back to Arizona to face auto theft charges. Convicted of auto theft, she was imprisoned. Nine months later, a camper found Mathis' decomposed remains on his ranch. Dugan was then tried for murder in a short trial based mostly on circumstantial evidence. During her testimony, Dugan said that Mathis believed that she had poisoned his breakfast food, though she claimed that he ate rotten meat in the form of a rabbit that had boils on it. Dugan also admitted she had sex with Mathis on a weekly basis and performed prostitution at the ranch. According to her, if Mathis "saw any of the men on the street that he thought was all right he would call them off and tell them to come on out to the house." She would perform sex acts for three dollars and give Mathis fifty cents from each transaction. Dugan claimed that "Jack," a teenage boy who had come to the ranch for work, accidentally killed Mathis with a retaliatory punch after Mathis beat him for refusing to milk a cow. According to her, Jack came to the house to tell her what he had done and she and Jack both attempted to revive Mathis with mouth-to-mouth resuscitation after removing his false teeth. When that failed to revive him, they loaded the body into the coupe and Jack drove it out alone to dump it, coming back at five o'clock in the morning. The prosecution proved to the jury's satisfaction that Dugan had murdered Mathis with an axe. After her conviction, in her final statement, she told the jurors, “Well, I’ll die with my boots on, an’ in full health. An’ that’s more’n most of you old coots’ll be able to boast on.” She would remain defiant to the end.
Imprisonment and execution
Dugan gave interviews to the press for $1.00 each and sold embroidered handkerchiefs she knitted while imprisoned to pay for her own coffin. She also made for her hanging a silk, beaded "jazz dress", but later relented and wore a cheap dress as she was worried that her silk wrapper "might get mussed." She remained upbeat, so much so that Time magazine called her "Cheerful Eva" in a March 3, 1930, story about her execution. The day before the hanging, there were rumors she planned to kill herself before being hanged. Her cell was searched and a bottle of raw ammonia and three razor blades hidden in a dress were confiscated. Dugan's appeal for clemency on the grounds of mental illness was denied and she was taken to the gallows at 5 a.m. on February 21, 1930. She was the first woman to be executed by the state of Arizona, and it was the first execution in Arizona history in which women were permitted as witnesses. According to a newspaper account, Dugan was composed as she mounted the gallows. She told the guards, "Don't hold my arms so tight, the people will think I'm afraid". She swayed slightly when the noose was put around her neck and shook her head in the negative when asked if she had any final words. The trap was sprung at 5:11; at the end of the drop, the snap of the rope decapitated her, sending her head rolling to a stop at the feet of the spectators. The grisly scene caused five witnesses to faint. Dugan was one of the last persons to be hanged by the State of Arizona, with only two more hangings – those of Refugio Macias on March 7, 1930, and Herbert Young on August 21, 1931 –– taking place. The gallows were replaced in Arizona by the gas chamber in 1934 and lethal injection in 1993. To date, Dugan is the only woman ever to be executed by the State of Arizona.