Born of a noble family, Cholokashvili was a decorated officer of the Imperial Russian Army during World War I. After the Russian Revolution of 1917, he served in the ranks of the Democratic Republic of Georgia. Following the republic's overthrow in a Soviet invasion in 1921, Cholokashvili, with a band of followers, took to the mountains and fought a guerrilla campaign against the Soviet government in the province of Kakheti. After a failed August 1924 anti-Soviet rebellion, during which Cholokashvili commanded the largest single rebel contingent, he fled to France, where he died of tuberculosis in 1930. His remains were reburied, in a state funeral, from the Leuville Cemetery near Paris to the Mtatsminda Pantheon in Tbilisi, Georgia, in 2005.