In Memory of
ROBERT FREE OSLER
Liutenant
48th Highlanders of Canada,, R.C.I.C
who died 32 age
25th July 1943
AGIRA WAR CEMETERY, SICILY
Osler, Robert Free ('21-'29), was born December 26,1910 at Toronto, Ontario. He came to T.C.S. at the age of eleven and took an enthusiastic part in all the activities of the School, becoming especially proficient at cricket. For two years he was a member of the first cricket team and also played on Bigside football and hockey, winning second team colours in both these sports.
He left the School from the Fifth Form, enetering the firm of Osler and Hammond, Investment Brokers, Toronto.
After a serious illness he decided to practice farming and attended O.A.C. in guelph. He later returned to the business world and after gaining experience in New York and London, joined a firm in Montreal.
He received his commission in the 48th Highlanders of Canada at the outbreak of war and went overseas with his regiment in 1940. He trained in England until 1943 whenn he took part in the invasin of Sicily. While serving as a platoon commander in "D" Company of his regiment, he was killed in action on July 25, 1943, when his men came under heavy machine gun fire during an attack.
The action is described by one of his men as follows: "All the way up the coast his Company, with "B" Company, had been taking the major part of the fighting. In the action on the night of Sunday, July 25, "B" Company attacked a ridge and "D" Company a high hill overlooking the ridge. They both came under enemy fire when they got to the top they came up against very heavy machine gun cross fire. Bob's Company suffered many casualties and Bobs himself got a blast from a machine gun which killed him instantly".
In the press report of the action it was stated that he deliberately drew the fire of the enemy in order to protect another party of his men.
Wedding of Robert Free Osler (Bobs) and Elizabeth Evelyn Harty (Betty), at Roselawn, Kingston, Ontario, on September 5, 1936.
Source: Hamilton Spectator, August 17, 1943
Jason Osler (Robert's grandson) becomes the first immediate family member to visit the grave.
Information courtesy of the 