The Canadian-born Holmes enlisted in the Grenadier Guards in London on 8 January 1940. While stationed at Wellington Barracks, he volunteered for Special Service and joined No. 8 Commando. He sailed to Egypt via South Africa, trained at Geneifa, and was hospitalized with typhoid. During recovery, he was sent to Crete in May 1941 as a reinforcement, attached to the Hampshire Regiment near Heraklion. He fought German paratroopers during the airborne assault and was evacuated under fire back to Egypt.
With No. 8 Commando disbanded, he rejoined the Guards, posted to the 2nd Battalion Scots Guards. Frustrated by inactivity and disciplinary issues, he applied to the SAS and transferred in January 1942. Before parachute training, he was recruited into the Special Boat Section (SBS) and sent to Beirut.
The SBS launched raids on Crete airfields ahead of the Sicily invasion. His team landed covertly and marched to Heraklion, only to find no aircraft present. Redirected to a nearby fuel dump, they planted explosives. Holmes narrowly avoided detection by German sentries and completed his mission. The resulting explosions destroyed multiple fuel stores. Other teams had mixed success—one destroyed aircraft at Kastelli, another found no targets.
Following Italy’s surrender, Holmes and S Squadron secured garrisons across the Dodecanese. At Leros, German forces countered, forcing their escape to Turkey. Instead of internment, they crossed Turkey to Syria and returned to base.
After ski training in Lebanon, Holmes resumed raids from Turkish waters. He led missions to Nissoros and other islands, conducting reconnaissance and sabotage. He later estimated landing on 15 islands during this period.
In June 1944, Holmes left Beirut, was promoted to Sergeant, and awarded SAS Operational Wings. He joined a 10-man team under Lassen in Italy, then Yugoslavia, where they destroyed a key bridge used by retreating German forces. After a firefight during extraction, they returned safely. In 1945, Holmes parachuted into Northern Italy to train partisans in weapons and explosives.
After the war, he became a schoolteacher and returned to Canada in 1966.
His Military Medal sold at auction on 18 August 2021 for £74,000 (plus £14,800 commission). Included were his SAS Certificate of Service (1942–1945), Soldier’s Service Book, SBS blazer badge, an un-named SAS certificate, copied photos, Buckingham Palace MM letter, and a copy of The SBS in World War II by Gavin Mortimer, where he is prominently featured.
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