During his 50 years as an active industrialist, Crosby owned thousands of acres of southern pine timberlands and numerous sawmills for converting trees into lumber.

Around age 20 and with only a third-grade education, Crosby left the family farm and set out on his own to labor in the timber industry – at first working behind oxen, hauling logs.

[6] Also in 1917, Crosby and partner, Lamont Rowlands, acquired the Rosa Lumber Company and sawmill near Picayune and approximately 3,500 acres (1,400 ha) of timberland in Hancock County, Mississippi.

[1] In addition to lumber production, Crosby added a broom-handle factory and a creosote treatment plant for preserving utility poles, pilings, and railroad ties.

[1] By 1931, the virgin pines on Crosby's timberlands around Picayune were almost exhausted and lumber markets had deteriorated as a result of the Great Depression.

[8] By the time the tung trees matured, the Crosby family had constructed their own tung-oil processing plant and paint factory in Picayune.

[11] In 1937, Crosby entered the naval stores industry by building a processing plant in Picayune to extract rosin from longleaf pine stumps left on his timberlands following logging.

[13] By the end of World War II, products from naval store industries were in high demand; consequently, the Crosby's expanded their business by purchasing stumping rights on thousands of cutover longleaf pine acres in Louisiana.

Crosby Sr. died November 24, 1948, at Foundation Hospital in New Orleans and was interred at Rose Hill Cemetery in Brookhaven, Mississippi.