Harold Jackson was Windsor’s first regular player in the National Hockey League. He played on two Stanley Cups during a career with the Detroit Red Wings and Chicago Black Hawks (modern-day Chicago Blackhawks). that spanned parts of eight seasons. An excellent high school track and field athlete, Jackson held a WSSA high jump record for 35 years.
Jackson, born in Cedar Springs, Ontario on August 1, 1918, came to Windsor at the age of six.
As a high school student, Jackson spent time at Kennedy Collegiate and Assumption in Windsor and St. Michael’s College School in Toronto. He developed a fine reputation in track and field, football, and hockey.
In three years of track and field competition at the WSSA and WOSSA levels, Jackson won a total of 25 medals in high jump, broad jump, hurdles, shot put, discus, javelin, and pole vault. A three-time Individual champion at the WSSA and WOSSA championships, Jackson was a three-time undefeated WSSA and WOSSA champion in the high jump and pole vault. He set two WSSA records in the high jump, plus one in the broad jump. At the WOSSA level, he set a further two high jump and pole vault records and one broad jump record. Significantly, he was the first WSSA athlete to clear six feet in the high jump. Incredibly, his 6’1” record stood from 1935 to 1970.
Jackson was also an excellent baseball player. He garnered attention as an outfielder while playing with Sports Incorporated and the Tecumseh Indians. Connie Mack, the legendary Philadelphia Athletics manager, is said to have approached him about signing a contract. Such was his earned reputation that, in 1947, Jackson was inducted into the Windsor Old-Time Ballplayers Association Hall of Fame.
Jackson, a team-first defenseman, reached the National Hockey League after toiling with the Windsor Wanderers in the MOHL and the OHA Junior St. Mike’s Majors from 1933 to 1936. All in all, he played eight years at hockey’s highest level, including one complete season with Chicago and four with Detroit. He contributed to Stanley Cup-winning seasons in 1938 and 1943 with the Black Hawks and Red Wings respectively. Jackson played a total of 350 NHL games, scoring 18 goals and adding 36 assists for a final total of 54 points.
During his professional hockey career, Jackson also spent time in the AHL with Buffalo, Cleveland, Indianapolis, and Providence.
Harold Jackson passed away on January 30, 1997.