The opposing GMs in the West final were junior teammates who have their names together on the Stanley Cup four times

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Edmonton Oilers and Dallas Stars at the start of the game

Jim Nill and Ken Holland were junior hockey teammates nearly 50 years ago, dreaming of becoming successful players.

Their names appear together on the Stanley Cup four times, but not as players. They achieved these championships through their front-office roles with the Detroit Red Wings from 1997 to 2008.

“We probably left three or four (titles) on the table. That’s how competitive it is,” Nill said. “But we had that good a team.” Now, as opposing general managers in the Western Conference final, only one of them will have the chance to win another Stanley Cup this season.

“We know each other well, so it means a lot to come in here and play against him,” said Nill, who is in his 11th season as GM of the Dallas Stars.

The top-seeded Stars lost the West final opener 3-2 in double overtime at home to Edmonton, where Hockey Hall of Fame member Holland is in his fifth season as general manager after 22 years in the same role with the Red Wings.

Nill was his assistant GM in Detroit before being hired by the Stars in 2013. The Stars are now in their third West final in five seasons.

Ken Holland speaks in a press conference

“Certainly a lot of the success that we had in Detroit, in my mind, is really a tribute to Jimmy Nill. … He ran the draft,” Holland said. “Obviously we go way back and we’re good friends. He’s done an amazing job here with Dallas. It was tough to see him leave.”

Jim Nill and Ken Holland were junior hockey teammates nearly 50 years ago, dreaming of big futures as players.

Their names appear together on the Stanley Cup four times, thanks to their roles in the Detroit Red Wings’ front office during the championship years from 1997-2008.

“We probably left three or four (titles) on the table. That’s how competitive it is,” Nill said. “But we had that good a team.” Now, as opposing general managers in the Western Conference final, only one of the old friends has a chance to win another Stanley Cup this season.

“We know each other well, so it means a lot to come in here and play against him,” said Nill, who is in his 11th season as GM of the Dallas Stars.

The top-seeded Stars lost the West final opener 3-2 in double overtime at home to Edmonton, where Hockey Hall of Fame member Holland is in his fifth season as GM after 22 years in that role with the Red Wings.

Edmonton Oilers players celebrates after winning the match

Nill was his assistant GM in Detroit before being hired in 2013 by the Stars, who are in their third West final in five seasons.

“Certainly a lot of the success that we had in Detroit, in my mind, really a tribute to Jimmy Nill. … He ran the draft,” Holland said. “Obviously we go way back and we’re good friends. He’s done an amazing job here with Dallas. It was tough to see him leave.”

Holland played in only four NHL games, three with Detroit in 1983-84. He finished his playing career the following season with the AHL’s Adirondack Red Wings, then became a scout in the organization.

When Nill retired as a player in 1991, he worked for three years as a scout in Ottawa. He then moved into a scouting role with the Red Wings, where he reunited with Holland, and got to work with GM Jim Devellano and nine-time Cup champion coach Scotty Bowman, who got the last three of those titles in Detroit.

Jim Neill talks to the reports

It was Devellano who first asked Nill about getting into the management side of hockey. “And I did, and I followed Kenny’s path, and he became one of my mentors. Kenny Holland, Jimmy Devellano, Scotty Bowman, I got to work under those men,” Nill said, referring to that trio of Hall of Famers.

“That meant so much to me to be able to learn from some of the greatest minds in the game, be a part of … their wisdom and their knowledge.”

Holland had stepped aside as the Red Wings’ GM and accepted a multiyear contract to stay with the organization as a senior vice president after former captain Steve Yzerman was hired as general manager.

But the Oilers quickly reached out to Holland about joining them, and he called Nill late one night from Europe to see what he thought.

“We walked through it and I gave him my words of wisdom and we talked, hashed through it,” Nill said. “Here he is, he’s now got them on the cusp, same place we are. He’s just done a great job in a high-pressure environment.”

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