Born in Indiana, Caylor specialized in ranch, roundup, and trail drive scenes. After studying in Indianapolis with portrait and landscape painer Jacob Cox (1810-1892), he cowboyed in Kansas, then across the West to California, sketching in his spare time. Caylor lived at Parsons, Kansas, painting portraits before moving to Big Spring, Texas, about 1890. He sketched from a mule-drawn hack and found acclaim for his authentic ranching subjects. J. Frank Dobie wrote that Caylor’s paintings found “deep appeal to men who drove up the trail, faced blizzards, loved horses, and regarded longhorns as a symbol for Texas itself.”
Caylor began ranching himself about 1898. Winter Gloom stayed in the same Big Spring family since 1898 when Caylor traded it for legal services due the loss of a ranch due to a severe winter. The painting may be an allegory about the difficulties of ranching, depicting his own abandoned ranch house in the background, its demise symbolized by the grave, and the emaciated coyotes fighting over the remains.
Purchase funded by Cynthia and Bill Gayden