A defenceman known for being steady in his own end, Harold Jackson spent parts of eight seasons in the NHL with Chicago and Detroit in the 1930s and 40s. Although he wasn't considered a rough player, Jackson utilized his 6' 195 lbs. body if a game turned more physical.He dressed for 38 games as a rookie with the Chicago Black Hawks in 1936-37, but his progress was curtailed by an injury the next season. He did return to play game one of the semi-finals versus Montreal during the Hawks' run to their Stanley Cup championship that spring, the team's second win after 1934.
Jackson spent most of the next four years with the AHL's Providence Reds and Indianapolis Capitals but did see spot duty with the Detroit Red Wings. In 1943-44 he started a four year term as a regular in Motown where he was a part of another Stanley Cup winner in 1944. He retired in 1948 after one season with the Buffalo Bisons of the AHL.