He served as the club's amateur director of scouting (1987-94), general manager of their American Hockey League affiliate (1994-97), then moved on to become the Original Six franchise's GM for 22 campaigns.
Despite only suiting up in three career games with the Red Wings, he spent 36 years with the team, captured 16 NHL division championships, six Presidents' Trophies and last, but certainly not least, hoisted Lord Stanley on four separate occasions.
He was a beacon of consistency season after season and will now try to replicate his blueprint in Edmonton, where he believes the building blocks to the foundation are already upright.
"When I think about the Edmonton Oilers and the players here, this franchise and the fan base, I just think there's an opportunity here for me to try to make a real positive impact," Holland said.
"After going through the process, all the conversations with Bob (Nicholson) and Daryl (Katz) and them giving me the full authority, that was important."
After three decades with Detroit's organization, the decision to leave was difficult. Red Wings Governor, CEO and President Christopher Ilitch offered Holland a position as the club's senior vice president, which would have cemented his career in The Motor City.
"I consider myself a people-person," the Oilers President of Hockey Operations said. "I'm going to be accessible, whether it's with the media or whether it's with the hockey people before the games. I'm going to be in the media lounge. I'm going to be available. I talk to people, I ask their opinions."
But when it's time to plan the Oilers course of action for the future, Holland and his management team are aware that things could look different.
"Ultimately, when it's time to make a decision, I'm going to rely on key people, on my gut instincts and my experience."
Those decisions, for Oilers Entertainment Group CEO and Vice Chair Nicholson, are Holland's to make.
"When Ken Holland is the General Manager, he'll be President and General Manager," said Nicholson. "He will have the final say in hockey decisions. My job will be to make sure Ken has that autonomy. We're going to even make that more crystal clear as we go forward.