At best, a cowboy’s life during the early 1900’s was hard. Long hours saddles in the hot sun or moving cattle through a driving blizzard. Little money, and plenty of lonesome hours spent drifting from place to place. His total worldly possessions included a horse, gun a good saddle and whatever he could stuff into a bedroll. In 1912, the Connolly Brothers, (Jack & Pat) moved from the copper rich mining town of Butte, Montana to the thriving commercial hub of Billings in eastern Montana. The two, along with another brother Andy, planted deep roots in the grass rich prairie cow-country. With their extreme skills, The Connolly Brothers Saddle Co. was formed, and soon became a favorite of the western cowhand. Prominent customers and riders of the famous Connolly saddle of this period included Jim and Walt Hill (builders of the Great Northern Railway), and famous bronc rider Al Grasfeilf. Perhaps the most noted cowboy to ride and promote the Connolly Brothers saddle however, was famous western artist and author Will James. He bought his first Connolly saddle second-hand as a young man while living in Canada. Upon moving to the Yellowstone Valley region, he became friends with the Connolly’s and rode nothing but their saddles until his death in 1942. Saddles were made under the brand of “Connolly Bros. Makers – Billings Montana” from 1912-1929 | 
