Frequenting the many saloons of Tombstone, Alvord started to socialize with some of the criminal elements and was known to get into frequent scuffles. As Slaughter began to chastise his actions, Alvord soured on both the Sheriff and the law.  

Alvord moved to Fairbank, Arizona in the early 1890’s and became a town constable. Continuing to drink heavily and cavort with known outlaws, he was soon asked for his resignation and he moved once again, this time, to Pearce, Arizona. There, he worked briefly as a deputy marshal for George Bravin in 1896, who was looking for a "tough nut" to make sure his  growing mining camp didn't get out of hand. However, after just six months, Bravin decided that there was no longer a need for the toughened lawman and Alvord moved on the Willcox. Little did Bravin know that the two would meet again under far different circumstances.

Again he obtained work as a town constable but commanded very little respect as by this time he had become a serious alcoholic. By the turn of the century, Alvord had given up on being a lawman and joined with the many outlaws he had befriended over the years. Starting with cattle rustling, he later formed a gang with Billy Stiles and began to commit armed robberies. After a foiled attempt to rob a Fairbank train and a run-in with tough lawman Jeff Milton, Alvord was arrested and taken to the Cochise County Jail. By that time, his former boss, George Bravin was working as a lawman in Tombstone and the two came face to face once again.

However, on April 7, 1900, as Bravin had some 25 prisoners housed in his jail, Billy Stiles went to visit Alvord and other gang members who were in the jail. He then held a gun to Bravin demanding the release of all of the prisoners and ended up shooting the lawman taking off two of his toes. The prisoners, including Alvord, then escaped.

The gang continued their criminal ways until both both Alvord and Stiles were arrested in December, 1903. Again they were incarcerated in the Tombstone Jail and again they escaped. Shortly later, Alvord got the idea that they would fake their deaths in order to get the law off their trail. The pair either killed two Mexicans or unearthed them from recent graves and sent them in sealed coffins to Tombstone. Spreading the word that the coffins contained their own outlaw bodies, the lawmen were suspicious and opened the coffins. Finding the moldering remains of the Mexicans, rather than the outlaws, they went after them again. 

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