Old friends Oilers, Stars GMs battle for chance to win another Cup

The two general managers of the teams that will meet in the NHL Western Conference Final have been teammates, friends, colleagues and co-workers for almost half a century.

Edmonton Oilers GM Ken Holland and his Dallas Stars counterpart, Jim Nill, first met as teenagers in 1975 as members of the Medicine Hat (Alberta) Tigers in the Western Canadian Hockey League — now Western Hockey League.

Holland was a 19-year-old goaltender in his second season with the team and Nill was 17 and a rookie right winger.

That was their only season as teammates. 

Holland moved on to professional hockey, first in the old North American Hockey League — which was the inspiration for the movie "Slap Shot" — and then to the American Hockey League, where he would spend the great majority of his nine-season professional career. Holland played a total of four National Hockey League games, one with the Hartford Whalers (now Carolina Hurricanes) in 1980-81 and three with the Detroit Red Wings in 1983-84.

Nill, on the other hand, spent most of 11 pro seasons from 1980-81 to 1990-91, in the NHL as a third-line forward with the St. Louis Blues, Vancouver Canucks, Boston Bruins, Winnipeg Jets and Red Wings in the NHL.

He spent his last pro season with Detroit's AHL affiliate, the Adirondack Red Wings.

At that point Holland was Detroit's director of amateur scouting.

But Nill did not immediately join his old teammate. He worked as a amateur and pro scout for the Ottawa Senators for three years before returning to the Red Wings organization in 1994, in Holland's old role, director of amateur scouting. 

That position came open because Holland was promoted to assistant general manager. For the next three seasons Holland, senior vice president Jimmy Devellano and coach/player personnel director Scotty Bowman combined to execute the duties of GM. Their were nickname was "The Three-Headed Monster".

Holland became the singular GM shortly after Detroit won the Stanley Cup in 1997. Nill was promoted to assistant general manager a year later, after the team won its second consecutive Cup.

That remained the set up for 15 years, which included two more Stanley Cups, in 2002 and and 2008. Nill had many opportunities to become a general manager with other teams during that time, including an offer from the Montreal Canadiens in 2012, but he wanted to wait for the right opportunity.

That came in April 2013, when Nill became the Stars' GM.

Holland remained the Red Wings general manager until April 19, 2019, when he stepped down to allow current Detroit GM Steve Yzerman to take the helm.

But Holland soon realized he had become too accustomed to running his own team to take a step back and became the Oilers' GM on May 7 of that same year.

Holland, 68, and Nill, 66, won four Stanley Cups together, but only one will have the opportunity to win Cup No. 5.