Orlando S. Holland was born around 1826 in Georgia. He married Rebecca P. Howard on December 28, 1845, and they had at least two children: William, born around 1847; and Isaac, born around 1849. They lived in Monroe County, Georgia, and he worked as a merchant. By 1850, he owned $800 of real estate. His wife died in June 1857, and he married Lucy P. Freeman on January 29, 1859. They had at least three children: Mattie, born around 1860; Paul, born around 1862; and Lilie, born around 1864. By 1860, he was working as an editor in Clarke County, Mississippi. He owned $3,000 of real estate and $1,585 of personal property.

 

He joined the Confederate army, and he served as lieutenant colonel of the 37^th Mississippi Infantry. He eventually earned a promotion to colonel. The regiment took part in the Vicksburg campaign, and Union forces captured it when the city surrendered in July 1863. He was eventually exchanged, and he returned to action. The regiment participated in the Atlanta campaign, and it surrendered again as part of General Joseph E. Johnston’s Army of Tennessee on April 26, 1865. He received a parole on May 2, 1865.

 

He settled in Mobile, Alabama, after the war, and he earned a living as a clerk. By 1870, he owned $1,000 of real estate. He died in Columbus, Georgia, on March 29, 1875, during a shoot-out with a local police officer.

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