Edmonton Oilers general manager Ken Holland speaks during a news conference in Edmonton, Alberta, on May 7, 2019. Holland and Dallas Stars GM Jim Nill were teammates in junior hockey nearly a half-century ago with big aspirations as players. Their names are together on the Stanley Cup four times, not as players but rather for their front-office roles with the Red Wings during Detroit's run of championships from 1997-2008. Now they are general managers of opposing teams in the Western Conference Finas, old friends both hoping to get to another Stanley Cup. (Jason Franson/The Canadian Press via AP)

Their names are together on the Stanley Cup four times, not as players but rather for their front-office roles with the Detroit Red Wings during that run of championships 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.”

Since they are opposing general managers in the Western Conference final, only one of the old friends will get the opportunity this season to maybe win another Stanley Cup.

“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.

Dallas Stars general manager Jim Nill speaks to reporters during a news conference at the NHL hockey team's practice facility in Frisco, Texas, June 8, 2023. Ken Holland and Nill were teammates in junior hockey nearly a half-century ago with big aspirations as players. Their names are together on the Stanley Cup four times, not as players but rather for their front-office roles with the Red Wings during Detroit's run of championships from 1997-2008. Now they are general managers of opposing teams in the Western Conference finals, old friends both hoping to get to another Stanley Cup. (AP file photo)

The top-seeded Stars dropped 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 since the end of his 22 years in that same role with the Red Wings. Nill was his assistant GM in Detroit before getting 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 said he and Nill spoke before the series but probably wouldn’t talk again until it was over. There was also a group text initiated by Ryan Martin, another former Red Wings front-office member who is now assistant GM for the New York Rangers, who are in the East final.

“That’s kind of strange, I guess, to see three of us in the final four,” Holland said.

Game 2 in the West is tonight in Dallas before the series shifts to Edmonton.

Dallas Stars general manger Jim Nill accepts the Jim Gregory General Manager of the Year award during the first round of the NHL hockey draft on June 28, 2023, in Nashville, Tenn. (AP file photo)

The relationship between the current GMs began in 1975-76, their only season playing together for the Medicine Hat Tigers in what is now the Western Hockey League. Holland was a 20-year-old goalie when Nill joined the team as a 17-year-old forward.

“He kind of took me under his wing a little bit,” Nill recalled this week. “So we built a relationship there … (went) our own ways playing pro hockey.”

Nill played 524 NHL games over nine seasons for five teams. The last was the Red Wings from 1987-90, when Holland was in their scouting department.

The only time Nill played in a Stanley Cup was at the end of his rookie season in 1982 with Vancouver, which was swept in four games by the New York Islanders. Nill had been traded to the Canucks from St. Louis late in that season.

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.

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 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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AP NHL playoffs: https://apnews.com/hub/stanley-cup and https://www.apnews.com/hub/NHL