He served as a child soldier during the American Civil War, protecting frontier settlements from Comanche raids while the older rebels engaged the Union Army.

After the Comanche Wars, Reynolds participated in the cattle drives from Texas to Kansas until being elected sheriff of Throckmorton County in 1885.

He then took his portion of the livestock and settled at a ranch in Pleasant Valley, a troubled region in a time known as the Tonto Basin War between feuding settlers.

When the situation in Pleasant Valley became intolerable, Reynolds moved his family to Globe, where he was elected sheriff in November 1888.

Reynolds was ordered to command the procession, with Sheriff William A. Holmes and coach driver Eugene Middleton as a company.

The party stopped at Kelvin, Arizona, on the Gila River, for the first night, and then set out for Casa Grande early the next morning.

After the murders, the United States Army launched a campaign to catch the fugitives, and by October 1890, all were caught except the Apache Kid.