Jack Raleigh was born in Kenora, Ontario on May 10, 1924. Raleigh was a phenomenal first baseman, second baseman, and shortstop, though first base was always his favorite position. Raleigh was known as a daring baserunner, who once stole home in a triple steal against Winnipeg at Osborne Stadium. In 1941, with East Kildonan, Raleigh won 28 consecutive games with a .300 batting average. His team then went on to be Winnipeg junior champions in 1942 and ’43. Throughout 1944 and 1945, Raleigh played with the Navy team in Victoria, BC. Following WWII, he returned to Winnipeg to play for the CUAC (Canadian Ukrainian Athletics Company) Blues, who were runners up in the Winnipeg League to Transcona in 1946. In 1948 Raleigh had an all-star season with the ANAF (Army Navy Airforce) Vets, and the next year he was their playing-manager. He then spent one more season with the Vets before returning to the Blues, where he led his team to a Winnipeg League title in 1950. Raleigh then spent one more successful season with the CUAC Blues before moving to Portland, Oregon the next year.