Oilers, Stars GMs face off in Western Final after success with Red Wings

DALLAS -- Ken Holland and Jim Nill have their names on the Stanley Cup together four times. They were on the management team when the Detroit Red Wings won the Cup in 1997, 1998, 2002 and 2008.

Now they’re facing each other as general managers of different teams in the Western Conference Final, Holland leading the Edmonton Oilers, Nill the Dallas Stars. Game 1 is at American Airlines Center on Thursday (8:30 p.m. ET; MAX, truTV, TNT, SN, TVAS, CBC).

Holland has Edmonton in the conference final for the second time in three seasons. The 68-year-old is looking to add another championship to a resume that already has him in the Hockey Hall of Fame.

“Obviously, we go way back, and we’re good friends,” Holland said at the Oilers hotel here Wednesday. “He’s done an amazing job here with Dallas.”

Nill has Dallas in the conference final for the second straight season and the third time in five seasons. The 66-year-old is looking to win the Cup for the first time as a GM.

“Our families are good friends,” Nill said at the Stars practice rink in Frisco, Texas, on Wednesday. “We know each other well and that. It means a lot coming here and playing against him.”

Holland and Nill go back to 1975-76, when they played for Medicine Hat of the Western Canada Hockey League, now known as the Western Hockey League. Holland was an overage goalie who turned 20 that season, Nill a 17-year-old forward. Nill said Holland took him under his wing, and they built a relationship.

After the Oilers defeated the Vancouver Canucks 3-2 in Game 7 of the second round Monday, Holland received a call Tuesday. It was from Bob Ridley, the longtime broadcaster and bus driver in Medicine Hat who retired in 2022. Holland said he asked him if he thought in 1975 he was driving two future NHL general managers who would meet in the final four almost 50 years later.

Holland and Nill reunited in 1994, when Detroit promoted Holland from director of amateur scouting to assistant general manager and hired Nill to replace him. After winning the Cup in 1997, the Red Wings made Holland GM, and Holland made Nill assistant GM. Holland and Nill worked in those roles for the next 16 years, their offices adjacent at Joe Louis Arena.

Nill also worked with two other Hockey Hall of Famers: Jim Devellano, who was the Red Wings GM until he became senior vice president in 1997, and Scotty Bowman, who was their coach until he served as a special consultant from 2002-08.

“I followed Kenny’s path,” Nill said. “He became one of my mentors. Kenny Holland, Jimmy Devellano, Scotty Bowman, I got to work under those men. That meant so much to me to be able to learn from some of the greatest minds in the game, being part of that, and they imparted their wisdom and their knowledge.”

Nill left the Red Wings to become the Stars GM in 2013. He brought director of amateur scouting Joe McDonnell and amateur scout Mark Leach from Detroit, and he inherited an amateur scout in Dallas by the name of Dennis Holland, Ken’s brother. Each remains in the same role today.

“Certainly, a lot of the success that we had in Detroit, in my mind, I really attribute to Jimmy Nill,” Holland said. “… It was tough to see him leave … and he’s built up a tremendous hockey team. They’ve got great vets, great young kids. They’ve done a great job in the draft. Good goaltending. So, we know we’re in for a tremendous series.”

Holland left the Red Wings in 2019. After stepping aside so they could hire Steve Yzerman as GM, he planned to stay in Detroit in an advisory role. But then the Oilers called, and he called Nill.

“He called me late at night -- he was over in Europe -- and said, ‘Jim, what do you think?’” Nill said. “And we walked through it. I gave him my words of wisdom, and we talked, hashed through it, and here he is. He’s now got them on the cusp, same place we are, and he’s just done a great job in a high-pressure environment. He’s in the Hall of Fame for a reason, and that’s why we’re here now.”

Holland woke up to a text Tuesday from Ryan Martin congratulating him and Nill for reaching the Western Conference Final. Martin was in the Red Wings front office from 2005-21, first as director of hockey administration for five seasons, then as assistant GM for 11. He is now an assistant GM with the New York Rangers, who are facing the Florida Panthers in the Eastern Conference Final.

“It’s kind of strange, I guess, to see three of us in the final four,” Holland said. “They want to win, and we want to win, so it’s going to be a great [two weeks].”