San Simon was established as the first Butterfield Overland stagecoach station inside the Arizona-New Mexico border early in 1859. Located on the flats, it was a welcome site for stage drivers after the dangerous trip through Doubtful Canyon. But it was just a short break as the next station was a dreaded run into Apache Pass.
During the 1880s the Southern Pacific Railroad built a station there and a small town grew up around it.
As late as 1900 the San Simon River ran from its headwaters and through the fertile San Simon Valley to the Gila River but a three-year drought 1902-1905, overgrazing and removal of the vegetation that held its banks in check hastened its deterioration.
During the 1880s San Simon the lair of a band of outlaws known as “Cowboys,” a loose-knit band of rustlers in Cochise County was known and was the scene of a voting scandal in November 1880. Johnny Ringo was a Pima County delegate to the Democratic convention. Republican Bob Paul, a tough, veteran lawman was running against the Democrat, Charlie Shibell, who was supported by the Cow-boys.
San Simon had only fifty eligible voters yet there were 103 ballots. When the ballots were counted there were 103 for Shibell and only one for Paul. Incidentally two of the election officials were Ike Clanton and Ringo, two men who didn’t exactly inspire trust. San Simon was in Pima County at the time. The election was eventually overturned and Paul was declared the Pima County Sheriff. In 1881 it would become Cochise County. The first sheriff of the new county was Johnny Behan so the Cow-boys wound up with another ally.