His soldiers called him Kutuzov, not because of his style of leadership, but because of his appearance: he was fat and flabby and wore a pince-nez.

He entered military service in 1885, graduating from the Nikolaev Engineering Institute, serving as a lieutenant with the elite Izmailovsky Life Guards Regiment.

Although his obese appearance was distinctly unmilitary, he had military talent and a reputation for calm bravery and quick decisive action.

In March 1918 May-Mayevsky fled to the Don region, and joined Mikhail Drozdovsky's White movement army as a common soldier.

By December 1918, May-Mayevsky was a general fighting on the Don front, including the Battle for the Donbas (1919).