Oleshev volunteered for the Red Army in 1918 and served in the Russian Civil War as a clerk at a field hospital.

After graduating from a course at the Frunze Military Academy, he was chief of staff of the Southwestern Front composite border detachment during its retreat across Ukraine after Operation Barbarossa.

During the summer the corps transferred to the Far East and fought in the Soviet invasion of Manchuria in August.

For his leadership in the offensive, Oleshev was awarded the title Hero of the Soviet Union.

Oleshev was the senior military adviser to the chief of combat training of the Bulgarian People's Army.

[1] Oleshev was born on 21 September 1903 in Poshekhonye in Yaroslavl Governorate in the family of a Kapellmeister in an artillery regiment.

From October, Oleshev served successively as assistant chief and outpost commander, assistant commander of a border detachment and head of the mobile group and 51st Troitsevo Savskogo (Grodekovskogo) Border detachment.

In May 1932, he became assistant chief of maneuver troops and senior commissioner of the 54th Nerchinsk Border Detachment.

Oleshev was head of the 1st Staff Department in the Transbaikal District NKVD Border Troops Office.

[1] In July 1940, Oleshev transferred to the NKVD Border Troops Kiev District Headquarters and a month later became the chief of the 2nd department of the 1st NKVD Kiev District Border Troops Division.

On 3 July, he was appointed military commandant of Minsk and oversaw the clearing of rubble from streets, the removal of unexploded ordnance and restoring of power and water supplies during the next ten days.

During the Battle of Memel, the corps, advancing in the vanguard of the 39th Army, captured Smalininkai on 9 October.

[6] For its actions in the subsequent Battle of Königsberg, the corps was awarded the Order of the Red Banner.

The corps reportedly crossed the Greater Khingan mountains quickly and advanced 950 kilometers, capturing Wangyemiao,[8] Liaoyang, Siping and Mukden.

On 8 September, Oleshev was awarded the title Hero of the Soviet Union and the Order of Lenin for his leadership.

Between December 1955 and March 1959, Oleshev was the senior military advisor to the Chief of Combat Training of the Bulgarian People's Army.