After he was passed over by Johnny Behan for the position of undersheriff, Earp thought he might beat him in the next Cochise County election. He thought catching the March 15, 1881 robbers of the Benson Stage (in which the driver and a passenger were killed) would help him win the sheriff's office. Earp later said that on June 2, 1881 he offered the Wells, Fargo & Co. reward money and more to Clanton if he would provide information leading to the capture or death of the stage robbers. According to Earp, the plan was foiled when the three suspects, Leonard, Head and Crane, were killed in unrelated incidents.
On August 12, 1881, Old Man Clanton and six other men were herding stolen cattle sold to him by William Brocius through Guadalupe Canyon near the Mexican border. Around dawn, they were ambushed by Mexicans dispatched by Commandant Felipe Neri in what became known as the Guadalupe Canyon Massacre. Old Man Clanton and five other men were killed in the ambush.
Clanton had told others that Doc Holliday, Virgil Earp, Wyatt Earp, and Morgan Earp had all confided in him that they had actually been involved in the Benson stage robbery. On October 25, 1881, while Clanton was in Tombstone, drunk and very loud, Holliday accused him of lying about the Benson stagecoach robbery. Tombstone City Marshal Virgil Earp intervened and threatened to arrest both Holliday and Clanton if they did not stop arguing, and Holliday went home.
Clanton was later accused, along with his brother, Phin Clanton, and friend Pony Diehl, of attempting to kill Virgil Earp on December 30, 1881, a shooting which left Virgil with a crippled left arm. Though Ike Clanton's hat was found at the scene where the ambushers waited, a number of associates stood up for him, saying that he had been in Contention that night, and the case was dismissed for lack of evidence.