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Leonard (Red) Kelly, then-Toronto Maple Leafs hockey coach, talks with then-general manager Jim Gregory, on Sept. 17, 1973.

John Wood/The Globe and Mail

Jim Gregory challenged Canadian chauvinism by importing two Swedish hockey players for the Toronto Maple Leafs, an important step in turning professional hockey into a global game centred on skill rather than thuggery.

Mr. Gregory, a hockey executive who has died at 83, was a creative thinker in a sport mired in an antediluvian culture. It was his ill fortune that a foremost proponent of the old ways happened to be his employer, the irascible and unpredictable Harold Ballard. For a year, Mr. Gregory had meetings with the boss at the latter’s temporary residences, the Kingston Penitentiary and the medium-security Millhaven Institution, while the team owner was serving a sentence for fraud.

Mr. Gregory spent 10 years as general manager of the Maple Leafs, a time during which he acted as a one-man firefighter snuffing Mr. Ballard’s many arsons. In a tumultuous decade, which would be best captured in a farcical episode in which a fired coach was rehired three days later only to be ordered to wear a paper bag over his head (he refused), the beleaguered Mr. Gregory managed to put on the ice teams that made the playoffs in eight of 10 seasons.

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Two of Mr. Gregory’s draft picks – offensive forwards Darryl Sittler in 1970 (No. 8 over all) and Lanny McDonald three years later (No. 4 over all) – were central to Toronto’s exciting style through the 1970s and both went on to be inducted into the Hockey Hall of Fame. He also drafted Tiger Williams, another fan favourite and a noted scofflaw who became the league’s all-time leader in penalty minutes, a nod to the realities of an era in which star players needed to be protected by brawlers.

At the time, the Canadians who ran NHL teams felt Swedish players were too soft to survive the league’s cutthroat game. Based on the scouting of Gerry McNamara, the Leafs signed winger Inge Hammarstrom and defenceman Borje Salming. The forward averaged more than 20 goals a season in four campaigns with the Leafs, a modest contribution, while the fearless Mr. Salming became an all-star and a Hall of Famer who combined mobility and scoring talent with a rugged disposition.

Mr. Gregory was a squat, stocky man with a dark complexion, a permanent five o’clock shadow and a thick black unibrow. He offered a calm, soft-spoken presence at Maple Leaf Gardens, a home to the hockey team as well as to travelling circuses, not to mention the circus conjured by the owner’s whims and prejudices.

“A lot of things Harold did were erratic,” Mr. Gregory once said. “He wasn’t patient a lot of the time.”

The team the general manager tried to build was eviscerated when more than a dozen players fled to the rival World Hockey Association, where offers of higher salaries were not matched by the parsimonious Mr. Ballard.

As a National Hockey League executive, Mr. Gregory encouraged the use of video replay on controversial plays. For more than three decades, he read aloud the names of picks in the annual NHL entry draft, making him a familiar face to generations of hockey fans.

As chair of the Hockey Hall of Fame selection committee, Mr. Gregory had the pleasant task of informing newly elected members of the good news. When he was too sick to attend meetings in 2007, the committee voted to induct him into the hall as a builder in recognition of his half-century as a hockey executive and administrator.

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After a decade of poor health, including a serious heart attack suffered in the NHL’s Toronto offices in 2009, which left him in critical condition, Mr. Gregory died at his home in suburban Toronto on Oct. 30. He leaves his wife of 60 years, the former Rosalie Bruno, whom he met on a blind date. He also leaves a son and three daughters, 13 grandchildren, two great-grandchildren, two brothers and two sisters. He was predeceased by a brother.

Hockey Hall of Famer Jim Gregory, seen here at the Hall in Toronto in November, 2013, spent 10 years as general manager of the Leafs.

Frank Gunn/The Associated Press

James Michael Gregory was born on Nov. 4, 1935, in Port Colborne, Ont., and grew up in Dunnville, a town 35 kilometres to the west. He was one of six children born to Henry Gregory, a stationary engineer from Salford, England, near Manchester, and the former Catherine Cecilia Gandour, known as Pearl. She was a bookkeeper before her marriage and one of five daughters born to Michael Gandour, a Dunnville fruit and confectionery merchant originally from Lebanon. Henry Gregory, whose own father died in Malta in 1915 of wounds suffered at Gallipoli, signed up for military service soon after the outbreak of the Second World War, though he was never sent overseas as he wished.

In Dunnville, population about 5,000, young Jim starred as a track athlete, as well as on the football gridiron, the baseball diamond and the hockey arena. Eager to play junior hockey, he followed three cousins to St. Michael’s College, a private Catholic boys’ school in Toronto known as a hockey hotbed. One of his roommates in Tweedsmuir House was Dick Duff, who would go on to win six Stanley Cup championships (twice with the Maple Leafs and four times with the Montreal Canadiens).

Mr. Gregory’s own dreams of playing in the NHL were stymied by his poor skating. The Grade 12 student was twice cut from the school’s junior-B hockey team and the youth was prepared to leave the school to try out for a team in Hamilton when persuaded by homeroom teacher David Bauer, soon to be ordained as a priest, to help out with the St. Mike’s junior-A team by keeping statistics and buying equipment. (Father Bauer went on to create a Canadian national amateur hockey team composed of student-athletes to compete at the Winter Olympics in 1964 and 1968.)

In 1959, by which time he was working as a sales representative for the consumer products manufacturer Colgate-Palmolive in Toronto, Mr. Gregory was hired by Conn Smythe to handle minor hockey teams in winter and to work in the Smythe family sand and gravel business in summer. Mr. Smythe nicknamed his new hire Pope, a reference to his Catholicism.

Mr. Gregory was an assistant coach and manager under Father Bauer when St. Michael’s won the Memorial Cup as Canada’s junior hockey champions in 1961. The Basilian priest led the team in a prayer of thanks in the locker room after the final game. Three years later, Mr. Gregory coached the Toronto Marlboros to the Memorial Cup championship with one of the greatest junior hockey teams ever assembled. Eleven of the Marlies went on to play in the NHL. In 1967, the Marlboros again claimed the junior title with Mr. Gregory as general manager.

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The 1966-67 season was a hectic one for Mr. Gregory, who also filled in as acting Maple Leafs general manager for 10 games while Punch Imlach recovered from illness. Those Leafs won the Stanley Cup in Centennial Year, the most recent championship for the storied team.

After a year as coach of the Vancouver Canucks of the Western Hockey League, Mr. Gregory spent a season as a scout before being promoted to replace Mr. Imlach as Toronto’s general manager.

Mr. Imlach won four Stanley Cups for Toronto in the 1960s, but by 1969 the team was tired and in disarray. The ownership was also in turmoil, as three owners – Mr. Smythe’s son Stafford Smythe, newspaper baron John W. Bassett and Mr. Ballard, a long-time friend of Stafford’s – jockeyed for control after an RCMP raid led to charges being laid against the younger Smythe and Mr. Ballard. Mr. Bassett sold his shares and Mr. Smythe died suddenly at the age of 50, leaving Mr. Ballard as principal owner shortly before he was jailed.

The Leafs needed rebuilding. Early in his tenure, Mr. Gregory shocked fans by trading veteran defenceman Tim Horton to the New York Rangers for future considerations (which turned out to be veteran goalie Jacques Plante and wingers Denis Dupéré and Guy Trottier).

Unlike many of his counterparts in the expanded, 12-team NHL, Mr. Gregory was impressed by novel European approaches to the game. He marvelled at the Soviets practising deflections for more than two hours. In practices, he encouraged the development of patterns of play, instead of mere scrimmages.

He was also keen to sign other Europeans, notably Anders Hedberg and Ulf Nilsson, but Mr. Ballard was reluctant to spend more money on Swedes. The pair instead signed with the Winnipeg Jets of the WHA, where they were scoring sensations alongside Bobby Hull on what was the dubbed the Hot Line.

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The upstart league’s raids also cost the Leafs the likes of veteran goalie Bernie Parent, centre Jim Harrison, defencemen Jim Dorey and Rick Ley, as well as veteran winger Paul Henderson and Dave Keon, a stalwart for the Leafs who had first played for Mr. Gregory at St. Mike’s.

Savvy draft picks compensated somewhat for the loss of talent, as Mr. Gregory grabbed defenceman Ian Turnbull in the first round (No. 15 over all) of the 1973 draft and solid goalie Mike Palmateer with the 85th pick of the 1974 draft.

A willingness to experiment led to the hiring of Roger Neilson to replace Red Kelly as head coach in 1977. Captain Video, as he was known, introduced the study of videotape to the game. He was also a rule-bender and a tactician of rare creativity.

Mr. Ballard fired the innovative Mr. Neilson after a game in 1979 before reinstating him because he was unable to find a replacement. The owner ordered Mr. Gregory to tell the coach to come out behind the bench wearing a paper bag, which was to be lifted to reveal his identity as the game started. The humiliated coach refused.

At the end of the season, Mr. Ballard fired Mr. Gregory to replace him with Mr. Imlach. Mr. Gregory learned of his dismissal only when the NHL front office called to offer him a job. He became the director of the league’s Central Scouting Bureau.

When a 1988 university research paper accused the NHL of discriminating against French-Canadian hockey players, Mr. Gregory, who was in charge of the league’s 16 scouts, disputed the claim.

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“I think if you were to ask the 21 teams, they’d tell you they tried to pick the best guy,” he said. “It doesn’t matter if he is Chinese, Japanese, Lebanese, or Quebecese (sic).”

Mr. Gregory held a variety of titles with the NHL over 40 years, often serving as the league’s ambassador. He was one of hockey’s most beloved figures, a man who salvaged unused notebooks after each draft for distribution to needy schoolchildren.

He estimated he had witnessed more than 6,000 hockey games. His one great regret was in not having his name engraved on the Stanley Cup, an honour he should have received for his temporary role as general manager in 1967.

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