Sergeant Alexey Oleshko Honoured After 19 Years of Dedicated Service to the RMR

For nearly two decades, Sgt Oleshko was a familiar presence within the RMR, progressing from a young rifleman in Bravo Company to the appointment of Company Sergeant Major of Headquarters and Services Company. Along the way, he helped train, mentor, and lead generations of soldiers, leaving a lasting impression on the Regiment and those who served alongside him.

Sgt Oleshko enrolled in the Canadian Armed Forces Primary Reserve in May 2007. After completing Basic Military Qualification in Saint-Hyacinthe that summer, he continued his infantry training in Meaford and Valcartier, becoming a qualified infantry soldier in 2009. His early career included participation in Exercise NOBLE GUERRIER at Camp Shelby, Mississippi, in 2009, followed by NOBLE WARRIOR exercises in North Carolina and Virginia in 2012 and 2013. He also served domestically during Operation LENTUS in 2011, supporting flood-relief operations.

Promoted to Master Corporal in 2011, he quickly established himself as a capable junior leader and instructor. Following his promotion to Sergeant in 2015, he served as both a Section Commander and Platoon Second-in-Command in Bravo Company, developing the soldiers under his command while contributing to the unit’s operational readiness. His subsequent appointments included Company Quartermaster Sergeant of Bravo Company from 2019 to 2020 and Platoon Second-in-Command of Depot Platoon from 2020 to 2024.

In May 2024, Sgt Oleshko assumed his final major regimental appointment as Company Sergeant Major of Headquarters and Services Company. Entrusting a Sergeant with responsibilities normally associated with a more senior rank reflected the confidence the Regiment placed in his professionalism, judgment, and leadership.

A Legacy of Mentorship and Excellence

Perhaps Sgt Oleshko’s most enduring contribution was his dedication to developing other soldiers. Over the years, he instructed on numerous Basic Military Qualification courses and Infantry DP1 training, helping transform civilians into soldiers and junior soldiers into capable leaders. His own performance consistently reflected the standards he expected of others. In 2009, he received the Colonel Trent Cup, awarded to the Regiment’s top performer in physical fitness. In 2019, he earned the Regimental Sergeant Major’s Trophy, recognizing exemplary leadership, professionalism, conduct, and dedication. In 2023, he added the RMR Best Rifle Shot Trophy to his accomplishments.

His contributions also extended into regimental life beyond the parade square. He served as Vice-President and later President of the Junior Ranks Mess Committee, and subsequently held responsibilities within the Warrant Officers’ and Sergeants’ Mess Committee. Outside the military, Sgt Oleshko successfully balanced his Reserve commitments with a demanding civilian career, earning a Bachelor’s degree in Accountancy in 2015 and completing the requirements for his Chartered Professional Accountant designation in 2017.

Throughout his service, he was supported by his wife, Cristina, and their two sons, Max and Daniel. The Regiment recognizes that 19 years of military service also represent countless sacrifices by the families who make that commitment possible. His service was formally recognized through the award of the Canadian Forces’ Decoration (CD) and the King Charles III Coronation Medal.

Although Sgt Oleshko officially concluded his military career in May 2026, the October gathering provided an opportunity for the regimental family to recognize his accomplishments and thank him personally. During the ceremony, the Commanding Officer presented him with a commemorative shadow box marking his years of service.

Those who served with Sgt Oleshko will undoubtedly remember his attention to detail, insistence on doing things properly, and commitment to maintaining high standards. They may also remember his determination to ensure that everyone spelled his surname correctly: O-LESH-KO! It was a fitting detail for a soldier whose professionalism, precision, and consistency helped define his military career.

As the gathering concluded, attendees assembled for a group photograph in front of the Regiment’s memorial tablet on the parade square, connecting the occasion with the RMR’s long tradition of service and remembrance. After 19 years, Sgt Oleshko leaves behind more than an impressive record of qualifications, appointments, and awards. His true legacy is reflected in the soldiers he trained, the leaders he mentored, and the friendships forged through nearly two decades of shared service.

The entire RMR regimental family extends its sincere congratulations and appreciation to Sgt Oleshko, Cristina, Max, and Daniel, and wishes them every success and happiness in the years ahead.