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Larry Hillman, Toronto Maple Leaf defenceman, receives the Eddie Shore Award from general manager Punch Imlach in 1961. Mr. Hillman has died at 85.Turofsy

Larry Hillman first won a Stanley Cup at age 18, the youngest player ever to do so. He went on to win the trophy symbolizing hockey supremacy another five times.

Mr. Hillman, who has died at 85, was a steady defenceman whose quiet, diffident personality was reflected in his play on the ice. He delivered bone-rattling body checks without incurring too many penalties, and he had a reputation late in his career as a stay-in-his-home defenceman known for protecting his own net, making him a popular teammate with goaltenders.

He was one of the most travelled hockey players of his era, suiting up for eight National Hockey League clubs.

“Hillman is the most underrated player in the league,” Punch Imlach, his coach and general manager with the Toronto Maple Leafs, said during the 1967 Stanley Cup finals. “He doesn’t get caught [out of position] like he used to. Nobody has worked harder to improve himself.”

The defenceman won his fifth championship days later, though in the following offseason he and Mr. Imlach had an infamous standoff during contract negotiations. The boss fined him $100 for every day he refused to sign. In response, the player imposed what came to be known as the Hillman Hex, a curse on the team’s prospects of winning the Stanley Cup.

Lawrence Morley Hillman was born in the mining town of Kirkland Lake, Ont., on Feb. 5, 1937. He was one of five children born to the former Winnifred Aileen Cascadden and Arthur Ray Hillman, a farmer from southwestern Ontario whose skills on the softball diamond brought him north during the Depression to take a job in a gold mine and a starting spot on the company’s fastpitch team.

All three Hillman sons – Floyd, known as Buddy, Larry and Wayne – would join their father on the diamond but more notably all three played defence for NHL teams.

Larry Hillman was just 15 when he headed south to play junior hockey with the Windsor Spitfires for the 1952-53 season. Two seasons with the Hamilton Tiger Cubs led to a tryout with the parent Detroit Red Wings near the end of the 1954-55 season.

The rookie rearguard played six regular-season games and three playoff games with the Red Wings before being sidelined by a dislocated shoulder suffered when he crashed awkwardly into the boards in the semifinals against Toronto. Despite his absence in the seven-game final series against Montreal, his name was included on the Stanley Cup. Backed by the production of Gordie Howe, the Red Wings won the championship on April 14, 1955. Mr. Hillman had turned 18 just two months and nine days earlier.

The previous youngest player to have his name on the Stanley Cup was Gaye Stewart, who was 18 years, nine months and 21 days old when his Maple Leafs won the championship at the conclusion of the wartime season of 1941-42.

The NHL has since changed its rule on age eligibility, making Mr. Hillman’s accomplishment unassailable.

Competition for jobs was ferocious in what was then a six-team NHL, as Mr. Hillman spent more than a decade as a so-called yo-yo player, moving back and forth between parent clubs and their minor-league affiliates.

The defenceman laced up for Detroit and the Buffalo Bisons before being loaned for a year to the Edmonton Flyers. After two seasons with the NHL’s Boston Bruins, the club sent him to the Providence Reds, where he was named the American Hockey league’s outstanding defenceman.

Mr. Hillman in 1967.Handout

In the summer of 1960, Toronto claimed the defenceman in the intraleague draft. He bounced between the Maple Leafs and the Springfield Indians and the Rochester Americans.

Mr. Hillman’s name was engraved on all three Stanley Cups won by the Leafs in the early part of the decade, even though he played only a handful of regular season games in two of those campaigns.

For the 1966-67 season, Mr. Hillman was paired with the veteran Marcel Pronovost, an old teammate from Detroit.

“Playing with Marse is a big break for me,” Mr. Hillman told Rex McLeod of the Globe in 1967. “I just watch his moves and try to follow up.

“I played with Marse for a few games last year but then we were broken up and I got a shot with everybody. I guess it didn’t work out. You have to keep playing with a guy to learn his moves and make your own adjustments.”

The Leafs stunned the Montreal Canadiens by winning the Stanley Cup in the Centennial Year of 1967, spoiling Montreal’s plans to display the trophy in the Quebec pavilion at Expo 67.

In the summer, the defenceman asked for a salary of $20,000. Mr. Imlach refused to budge from an offer of $19,500. Mr. Hillman refused to sign, staging the longest holdout the league had seen in decades.

His stubbornness infuriated Mr. Imlach, who said: “There’s no way he’s going to get a paid holiday around here. If we can’t make a suitable deal for him, he’ll just sit out the year with no pay.”

He returned to action only after NHL president Clarence Campbell made a ruling in favour of the club. The Leafs fined Mr. Hillman $2,400 for his 24-day holdout. The defenceman vowed the team would not again win the Stanley Cup until he was paid back his fine.

“I never intended to become a labour agitator,” Mr. Hillman said a year later, “but I had to stick by my guns. It was a season I’d like to write off.”

After a forgettable 1967-68 campaign, the defenceman’s rights were acquired in the summer by the New York Rangers and immediately claimed by the Minnesota North Stars. He played only 12 games for the expansion team before he was claimed on waivers by the Pittsburgh Penguins, who then traded him to the Canadiens.

He won his sixth Stanley Cup in the spring of 1969, though as a spare player he skated only in a single playoff game for Montreal.

The defenceman also played for the NHL’s Philadelphia Flyers, Los Angeles Kings and Buffalo Sabres before jumping to the rival World Hockey Association with the Cleveland Crusaders and Winnipeg Jets.

As a coach, he guided the Jets to the Avco Cup championship in 1978.

In 790 NHL games as a player, Mr. Hillman scored 36 goals with 196 assists. He had 579 penalty minutes. In 74 playoff games, he scored two goals with nine assists.

In 2016, the Maple Leafs placed him No. 96 on their list of all-time top 100 players.

In summers, he was a noted fastball pitcher in Kirkland Lake with the Joe Dash Red Raiders, a team which included his two brothers as well as NHL players Dick Duff and Ralph Backstrom.

After retiring from hockey, Mr. Hillman, a pilot, operated a fly-in vacation lodge in Northern Ontario.

Mr. Hillman died on May 31 in Sudbury, Ont. He leaves Elizabeth, his wife of 38 years, as well as their daughter. He also leaves two sons and two daughters from an earlier marriage; six grandchildren; six great-grandchildren; and, a sister, Sharon Savage. He was predeceased by sister Shirley Warchol, and by brothers Floyd and Wayne.

More attention has been paid to the so-called Hillman Hex as season after season passed without another Maple Leafs championship. In 2017, as the 50th anniversary of the Leafs’ last Stanley Cup victory approached, Sports Illustrated magazine reported the hockey club repaid Mr. Hillman his fine of $2,400 with interest. The grateful former player proclaimed his hex at an end.

Alas, for Maple Leaf fans, the club has now gone 55 seasons – and counting – without a championship.