On March 15, 1881, Head and outlaws Bill Leonard and Jim Crane ambushed a stagecoach about a mile outside Contention, Arizona. The coach, carrying $26,000 in Wells Fargo money and eight passengers, was waylaid while trying to navigate a steep grade. To conceal their identities, the robbers wore wigs and false beards. Guarded by lawman Bob Paul, gunfire erupted, and stagecoach driver Budd Philpot and a passenger were killed, and stage robber Bill Leonard was wounded. In the meantime, the horses bolted, Bob Paul got the stage under control, and the would-be robbers fled.
Bob Paul and Wyatt Earp began to investigate. They suspected that a man named Luther King was one of the robbers, and Morgan Earp arrested him. However, King said he had only been there to hold the horses and implicated Harry the Kid, Crane, and Leonard. Afterward, King escaped jail. In the meantime, Wells Fargo offered a reward for the three other men of $2,000, each dead or alive.
A few months later, in June, the three outlaws attempted another robbery at a store in Eureka, New Mexico. However, owners Bill and Ike Haslett fought back, and Harry Head and Bill Leonard were killed. Crane was able to escape and orchestrated the killings of both Haslett brothers.
Later that month, Crane and Curly Bill Brocius, Frank Stillwell, Pony Diehl, Pete Spence, and at least five other men hunted down the Haslett brothers. When they found them, the Hasletts fought a good fight, killing two and wounding three of Crane’s party before they were overwhelmed and killed.
The Arizona Star reported the gunfight on June 23, 1881:
“The killing of Bill Leonard and Harry, the Kid, at Eureka, New Mexico by the Haslett brothers, has been summarily avenged. It appears that a cowboy named Crane organized and led a band of congenial spirits in the work of vengeance. They followed the Haslett boys for some twenty-six miles from Eureka before overtaking them, and, as soon as they came up with them, the fight to the death commenced. The Haslett boys were game and made a brave fight killing two and wounding three of the Crane party, but being overpowered were finally killed.”