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.

[4] With the outbreak of World War I in 1914, Cholokashvili was recalled to active duty and assigned to lead a cavalry squadron on the Austro-Hungarian front.

During the Battle of Sarikamish in December 1914, he commanded a cavalry squadron under General Vasily Gabashvili and distinguished himself by capturing and defending a strategic fortification known as "the Eagle's Nest" against the overwhelming Ottoman troops.

After treatment at the St. Nino Hospital in Tiflis, he was enlisted in the nascent Georgian Cavalry Legion which marched into Persia as part of General Baratov's 1915–1917 expedition.

In this capacity, Cholokashvili served in the campaigns against Armenia (December 1918 – January 1919), White Russian forces (February–October 1919), pro-Bolshevik rebels in Gori (November–December 1919), and in a raid in the Batumi Oblast (February–March 1920).

In his 1976 study of the Georgian revolt, the Soviet Russian historian Trifonov wrote that "the most numerous and dangerous band was that of Chelokaev.

The Mensheviks treated Cholokashvili, a former nobleman, with suspicion, but were eager to exploit his standing among the Georgian nationalists for their political ends.

On the other hand, Kakutsa (and many of his fellow military officers such as General Giorgi Kvinitadze) contemned the Mensheviks for their alleged disregard of national interests and indifference to the army.

Beria's designs were foiled as Kakutsa's health rapidly declined; he died of tuberculosis, in 1930,[6] at the Plaz-Coutant sanatorium near Passy, Haute-Savoie.

With the rise of nationalist and pro-independence movements in the 1980s, Kakutsa re-emerged as a major symbol of Georgian patriotism and resistance to the Soviet regime.

In October 1990, his closest companion and comrade-in-arms, the 94-year-old émigré Aleksandre Sulkhanishvili, returned from his 66-year-long exile to a hero's welcome in Tbilisi, bringing Kakutsa's banner to Georgia.

[12] On 20–21 November 2005, Cholokashvili's remains were brought to Georgia and afforded a state funeral, in the presence of high-ranking government and church officials and thousands of Georgians, at the Mtatsminda Pantheon.

[13] The same year, Tbilisi's Marjanishvili Theatre staged Levan Tsuladze's successful production of "Kakutsa Cholokashvili", an epic patriotic play by Guram Qartvelishvili.