Jack Wootton's father, William Greenway Wootton, was born in 1867 in Walsall, Staffordshire, England. He was a harness maker who married Agnes Mary Petch in her home town of Liverpool in 1901. Agnes had been born in 1877. In 1902 she gave birth to twin sons who didn't survive. When the family emigrated to Toronto in 1905, William and Agnes had two daughters, Jessie Annie and Edith Mary. In Toronto, the Woottons lived on Oak Street, near River and Gerrard Streets and welcomed Eleanor Margaret in 1907 and Agnes May in 1908.

In 1909, they relocated to 1548 Dundas Street West, near Dufferin Street, where William also conducted his harness work. Their son William George was born there in 1911 and Jack followed on March 9, 1915. As World War I was being fought overseas, William Sr joined the Canadian Expeditionary Force in February 1916. When he was young, he had served three years with the 4th Liverpool Artillery. William was 39 years old and knocked a few years off his age on his paperwork. He sailed to Liverpool in September 1916 and was sent to fight in France the next March as a gunner in the 48th Howitzer Battery of the Canadian Field Artillery. William had a good seven months, until October 1917 when he was admitted to hospital with nephritis, an inflammation of the kidneys. Within two weeks William had returned to England to recover. He arrived back in Canada in March 1918 and was invalided out of the army the next month.

In 1917, Agnes had moved the family to Weston and ultimately lived in a house on Victoria Avenue. When William returned, they bought a house at 15 Waterloo Avenue, near Dundas and Dufferin Streets. William continued to do his harness work from home. The family lived there until 1922. Agnes gave birth to a daughter in February 1922, who died when she was five days old.

With the increasing numbers of automobiles on the roads, the day of the horse and the related businesses were in decline. No doubt William was aware of his dwindling income and moved the family to 4186 Dundas Street West in Lambton Mills. He was located near the corner of Prince Edward Drive (named Lambton Road at the time) and took advantage of the need for a harness maker in agricultural Etobicoke. He became involved in the community and the family joined St. George's on-the-Hill church, where William was warden for several years.

Jack began school at Lambton Mills in 1922 and graduated Grade 8 in June 1929. He entered the year old Etobicoke High School that September where he played outside on the rugby team. During his high school career, he also played hockey and first base in baseball games. Jack proved to be clever with mechanical and electrical handiwork and handicraft in general.

William's nephritis had begun to trouble him again in the late 1920s and he passed away on January 11, 1931. Agnes waited until Jack had completed his year at Etobicoke before moving to 43 Gilmour Avenue, a couple of blocks from Western Tech. Jack went to school there that fall and graduated in June 1934 with his senior matriculation in Electrical Construction. He enjoyed his Electricity class and did well in Drafting and Arithmetic.

He started a job in November as a clerk at Terry Hardware on the southwest corner of Annette Street and Runnymede Road for $40 a month. By early 1936 Jack was earning $50 a month, but he was disillusioned with the job as the pay wasn't in keeping with the number of hours he found himself working. He quit in March. He landed a job in July at the Avis Marketeria, two doors west of his old home on Dundas Street in Lambton Mills. The Avises had been his family's neighbours. He became a clerk, truck driver and maintenance man for the store for $65 a month. Jack was able to take night school courses from 1937 to 1939 at Central Tech, learning about diesel engines. He quit his job in May 1939 to enlist with the RCAF as a mechanic. Whether he had military ambitions or he anticipated World War II is unknown.

He joined No. 110 (City of Toronto) Auxilliary Squadron which was an army co-operation squadron. Jack likely learned to maintain army vehicles along with aircraft. When war was declared on September 3, six days later Jack formally signed up with the RCAF for the duration. He was stationed at Camp Borden at the time and was learning his trade as an air engine mechanic, qualifiying as an “A” level air mechanic in March 1940 and was promoted to corporal in August 1940.

Jack had a girlfriend, Dorothy Rose Holland, whose family lived on Islington Avenue. They may have met at St. George's church as they were both members. When it became apparent that Jack would soon be transferred away from the Toronto area, he and Dorothy married in their church on November 22, 1940.

The air force was quickly assembling a program to train flying crews, which would become the British Commonwealth Air Training Plan. Flying schools were established on many existing airfields and with the increasing enrolment, new military airfields were being built across Canada. On November 25, 1940, the RCAF opened No. 6 Service Flying Training School (SFTS), three kilometres south of Dunnville, Ontario, near the mouth of the Grand River on Lake Erie. It was one of a cluster of RCAF bases in the region, including Jarvis, Hagersville and Welland, which provided the students with several options for a safe landing if they had difficulties in the air. An SFTS took pilots who had passed their 50 hour elementary training and gave them 9 weeks of advanced lessons that would lead to being awarded their pilot's wings. Later the course was extended to 16 weeks.