Norris followed through on the recommendation and Stewart was assigned to the Red Wings minor league affiliate, the Pittsburgh Hornets of the International-American Hockey League for the 1937-38 season. With no aspirations to join the offense, Stewart play in 48 games for the Hornets with his entire offensive contribution consisting of a lone assist.
Stewart would start the 1938-39 season with the Hornets, but after 21 (scoreless) games, he was called up to Detroit for his first taste of play in the NHL with the lackluster Red Wings, which would eventually amount to 32 games with credit for just one assist.
For the 1939-40 season, Stewart played in all 48 games of the Red Wings schedule, again scoring a single point for the season - only this time it was a goal! His hard hitting style made an impression around the league and got the rookie noticed.
Now regarded as the hardest hitter in the league, as evidenced by the numbers of injuries and scars he suffered as a result of hy physical style of play, he earned the nickname "Black Jack" Stewart, a name he did not care for, as he thought it made him sound like a dirty player. However, he did not help his case by being quoted as saying things such as "I don't use [my stick] for scoring, I use it for breaking arms."
"King" Clancy stated Stewart was not a dirty player, but was "the toughest son of a gun you'd ever want to meet", evidenced by his eventual total of over 200 stitches and once playing a full season despite a broken hand.
For the 1940-41 season, Stewart played in 47 games and produced a virtual offensive explosion of 2 goals and 8 points, four times his previous career total! The Red Wings finished third in the seven team NHL and were able to win two playoff series to make it to the Stanley Cup Finals.
Detroit again made it to the Stanley Cup Finals in 1942 after a regular season in which Stewart had 4 goals and 11 points.
In 1942-43, Stewart again had 11 points from 2 goals and 9 assists. Detroit finished first overall in the regular season in the now six team NHL following the loss of the New York Americans after the previous season. The Red Wings then defeated the Toronto Maple Leafs in 6 games before sweeping the Boston Bruins to win the Stanley Cup. Stewart played in all ten Red Wings playoff games, contributing a goal and 2 assists. Stewart was named as a First Team All-Star after the conclusion of the season.
Stewart's career was interrupted when he joined the Royal Canadian Air Force. He was able to remain in Canada during his tour of duty as an aircraft mechanic, which did allow him some time for hockey, playin in 7 games with the Montreal RCAF team om 1943-33 and a pair of games with the Winnipeg RCAF club in 1944-45.
He returned to the NHL with Detroit for the 1945-46 season, picking right up where he left off with a Second Team All-Star selection to go with a new career high 15 points and led the NHL in penalty minutes with 73.
Another Second Team All-Star selection was in the offing for 1946-47 thanks once again to Stewart's hard hitting, excellent defensive play after a season that saw him set a career high with 5 goals.
Before the 1947-48 regular season began, Stewart was selected to play in the first of the annual NHL All-Star Games, which in the early days was not only played prior to the season began, but with just six teams playing in one division, the game paired the defending Stanley Cup champions against a team of all-stars chosen from the five remaining clubs. Stewart was one of only three Red Wings chosen, along with fellow defenseman Bill Quackenbush and forward Ted Lindsay.
Stewart established a career high offensively in 1947-48 when he matched his 5 goals from the season before while being credited with 14 assists for 19 points while playing in all 60 of Detroit's games. Stewart also played in the All-Star Game prior to the season and was named a First Team All-Star after the conclusion of the season, during which the Red Wings returned to the Stanley Cup Finals.
He played in his third All-Star Game prior to the start of the 1948-49 season and then went on to set a career high in penalty minutes with 96. Stewart was named as a First Team All-Star for the third time as the Red Wings once again made it to the Finals, only to be swept by Toronto yet again.
For the fourth consecutive season, Stewart had a place in the NHL All-Star Game prior to the 1949-50 season. He chipped in his customary 14 points as Detroit went 37-19-14 to finish first, 11 points clear of the second place Montreal Canadiens. During the playoffs, Detroit defeated their recent nemesis Toronto 1-0 in overtime of Game 7 and then defeated the New York Rangers 4-3 in double overtime of Game 7 to win the second Stanley Cup of Stewart's career.
It would prove to be his final game as a Red Wing, as Stewart was a key piece in a massive nine player trade, at the time the largest in NHL history, that sent him and four teammates to the Chicago Black Hawks, who would name Stewart as their team captain and assistant coach, such was the level of respect he commanded.
Unfortunately, Stewart would only play for two months before suffering a spinal injury that many believed would end his career. He was told he was lucky he could still walk and to not risk any further play. Instead, Stewart had the ruptured disc removed and signed with Chicago for the 1951-52 season.
Injury struck again though, and he missed several weeks of play with a minor skull fracture early in the year. After he recovered, he returned to play, but with the lowly Black Hawks mired in last place with no chance to make the playoffs, Stewart asked Chicago to release him in mid-February so he could start his coaching career. Over his two seasons with the Black Hawks, "Black Jack" played in a total of 63 games with a goal and 6 assists.
The first two seasons of his coaching career were as a player/coach with the Chatham Maroons in the Ontario senior league starting in 1952-53. He played 45 games his first season with 2 goals and 27 assists and 134 penalty minutes, still living up to his credo of "hit 'em hard and hit 'em often". He played another 21 games while coaching the Maroons in 1953-54 before retiring as a player.
His coaching career would continue at various levels until 1963 after which he focused on his love of harness racing, acting as a judge with the Ontario Racing Commission for nearly 30 years.
His final NHL totals were 565 games played with 31 goals and 84 assists for 115 points and 765 penalty minutes and two Stanley Cups. Stewart was inducted into the Michigan and Manitoba Sports Halls of Fame, was named a charter member of the Red Wings Hall of Fame in 1944 and was inducted into the Hockey Hall of Fame in 1964.
Today's featured jersey is a 1949-50 Detroit Red Wings Jack Stewart jersey from his final season as a Red Wing as they won the second Stanley Cup of Stewart's career.
A unique feature of the Red Wings jerseys was putting the captain's C and the assistant captain's A's in a white diamond shape.
Detroit debuted this jersey in 1932-33 when new ownership changed the name of the team from the Falcons to the Red Wings. The only changes to this jersey since then have been the addition of sleeve numbers and names on the back for one of the most enduring jerseys in NHL history.