John Lewis Shepherd, known as Jack, was born on November 7, 1921 in Bronte, Ontario. His father, John Sr, also known as Jack, was a labourer renting property to the west of the village on Lake Ontario. Today it is all part of Oakville. He and his wife Marion settled there after the First World War. Jack Sr was born in England in 1888. Marion Brown Wood was a Scot, born near Dumfries in southern Scotland in 1892. They married in Morpeth, England in November 1919 and were living in Bronte at the time of the 1921 census. They both stated that they came to Canada in 1907. Unless Marion was serving in the First World War, it is doubtful whether she came to Canada before her marriage. Jack Sr was a veteran of the recent war and it seems he fought for the British, not the Canadians, so he, too, may not have arrived in Canada until after his marriage.

 

After Jack, the couple had two daughters, Doris and Elsie. Jack should have started school in Bronte. They moved to Toronto by 1932, the first owners of what today is 45 Westlake Crescent. The street was called Payler Crescent until the late 1940s. Jack Sr took a job as a steel worker at the Canadian John Wood factory on Hanson Avenue, east of today's Monarch Park Collegiate. The company built water heaters. The Shepherds became members of the Church of the Resurrection on Woodbine Avenue.

 

Jack was a bit older than the others in his cohort, making it appear as if he wasn't enrolled for long in Bronte's school and may have started school late. He attended Danforth Park, probably for Grades 2 to 8. Jack's school career ended when he graduated Grade 8 in 1938. He was 16 and went to work as a garage mechanic's helper. Jack had a mechanical mind and also liked hunting and fishing. In 1940 he sustained a cut on his right wrist at work that put him on worker's compensation for two weeks.

 

After two years at the garage, Jack found a job at Canada Illinois Tool, a tool manufacturer which was making government gauges. It was located at Front and Sherbourne Streets. After he was with the company for a year, he apprenticed for two years as a precision grinder, but didn't complete the apprenticeship before he enlisted in the army on April 20, 1943. He stated that after the war he hoped to return to his job, to qualify as a machinist.

 

On November 6, 1942, Jack's sister Doris had married Jack Wisdom West. He was a recent observer graduate of the RCAF's training scheme and was about to leave for Britain. Doris continued to live with her family while her husband was away.

 

When he enlisted, Jack was 5'8.5” and 145 pounds. He was a redhead with hazel eyes. The army thought that he would be suitable in the Royal Canadian Engineers for trade training as a fitter or in the machine shop trades. He was made a sapper, the rank given to members of the army engineers. On May 14, he was sent to Newmarket for his basic training. When that was finished in mid-July, he was assigned to the Canadian Engineer Training Centre in Petawawa where he was a candidate for the auto trades. In September he was given a two week furlough and returned to Toronto. It wasn't long after that, on October 12, that he was given four more days of leave prior to being shipped to Britain. When he left Petawawa in early November, he was recommended for a mechanic's course and if there wasn't one available in Canada, it was suggested that he be given it overseas.

 

On November 4, he arrived in Debert, Nova Scotia. The camp was the final staging area for men embarking from Halifax. Jack spent Christmas there and sailed on December 27, spending New Year's at sea. He arrived in Britain on January 3, 1944 and appears to have been tested as a precision grinder, but on January 19, he failed to qualify which would have been a tremendous disappointment for him.

 

At the time, troops were flooding into Britain in preparation for the coming invasion of Europe. The army didn't seem to need any of Jack's skills and he was re-mustered into the infantry as a reinforcement. He became a private on April 26. Instead of being assigned to a unit that was stationed in Britain preparing for D-Day, he was assigned to the Royal Canadian Regiment (RCR) and embarked for Italy on May 3, landing on the 16th but he wasn't immediately deployed to the unit, probably for further training prior to his deployment.

 

In July, the mood at home became grim. Jack's sister Doris received a telegram that her husband was listed as missing when his plane didn't return to base in England.

 

On August 31, Jack, along with two officers and twenty-four other reinforcements, joined the RCR. He was posted to D Company. The regiment had fought in Italy since the Sicily landings a year earlier. After the liberation of Rome in early June, the Allies were now pushing north along the northeast coast of Italy towards Rimini. On the day Jack arrived, the regiment was at rest in the hilly region 10 kilometres south of Pesaro. The rest wasn't a long one and on September 2 the regiment moved out at 1130 hrs on troop carrying vehicles (TCVs) to the assembly area for the next battle. They arrived at 1500 hrs and were told that the plan was to cross the River Conca, going as far as possible on TCVs then moving on foot to establish a bridgehead on the other side of the river. The regiment moved forward at 2030 hrs, with D Company in the rear. All established a position across the river in the early morning of the 3rd. As they pushed farther in , they discovered they were fighting fierce German paratroopers. “A” Company suffered very heavy casualties and D Company was sent forward to replace it, continuing to attack a ridge. Six tanks arrived to assist the company. Jack saw several of his fellow soldiers killed or taken prisoner but the company had moved 550 metres forward. The next day at 2000 hrs D Company led yet another attack on the ridge. Their first objective was achieved in six minutes. The regiment's war diary noted that “a great dash was displayed by D Coy who went in with bayonets fixed in perfect extended line.” The company was up against machine gun fire and soon the attack was cancelled and the company was to re-assume its starting position.

 

At 0600 hrs on September 5, the regiment again attacked the ridge, but it was found that after heavy air bombing, the Germans had retreated and the ridge was captured by 0700 hrs. The next ridge was established as a target and the next morning at 0600 hrs, Jack's company along with two others began an assault. They advanced to within 140 metres of the ridge when the forward company, “A,” came under “murderous machine gun fire.” The company was practically destroyed, but in so doing, it protected the other companies behind it. The Hastings and Prince Edward regiment moved in to relieve the RCR.

 

At home, Doris received word that her husband was safe, probably parachuting into Allied territory, and was shipped back to Britain.

 

On September 15, as the RCR was moving to a new area, closer to Rimini, the enemy began shelling the road and the men jumped in the ditches for safety. It was over in 5 minutes and Jack's company continued on foot to the camp. The next day they were advancing near the airfield south of Rimini. During the morning they were subjected to heavy shellfire and prolonged fire fights. At 1000 hrs a platoon of D Company identified the enemy. At 1430 hrs they attacked, but the company's commanding officer was killed by shellfire at 1600 hrs. The next day the entire regiment inched forward, causing considerable German casualties. On the 18th at 2000 hrs they were ordered to a new position and it was thought that the German paratroopers were withdrawing. By now the regiment was on the outskirts of Rimini and on the 21st, the Canadians entered Rimini, which had been abandoned by the Germans.