The Detroit Red Wings had just ended their 42-year drought when, on July 18, 1997, they made arrangements to ensure their continued success. They implemented a plan that had been in the works for three years by promoting Ken Holland to general manager. At the same time, they established the parameters for keeping Coach Scotty Bowman and Senior VP Jimmy Devellano. Holland explained, “It’s been a long process to get to this point in time. We wanted to go with a traditional coach/GM setup.” Thanks to these moves, the Red Wings went on to win more division championships, conference titles, Presidents’ Trophies, and (most notably) Stanley Cup championships.

Holland found his calling as a GM. After being drafted in the 12th round in 1975, he struggled his way through eight seasons goaltending for the AHL. He only made one NHL appearance for the Hartford Whalers (a loss during the 1980-81 season) and three for the Detroit Red Wings (including one loss and one tie during the 1983-84 season). Having retired from playing in 1985, Holland scouted for Detroit and became the chief pro scout in 1989. Beginning in 1994, he served the organization as assistant general manager, apprenticing under Devellano. In 1997, he was promoted with a four-year contract that gave him full authority to make decisions on all hockey operations as Detroit’s GM. “Certainly, it’s a tremendous opportunity for me,” said Holland. “I’m excited about my new role in the organization. I’ve been training to reach this point for a long time, and I’ve had the opportunity to work with a lot of great hockey people.”

As Devellano had wished, he took a more backseat role as senior VP without GM responsibilities. He was looking ahead to retirement. He explained, “I feel much more fulfilled about it now that we’ve won a Stanley Cup here. We won a couple of Presidents’ trophies and appeared in the finals, and it’s been three pretty darn good years since I returned to a more active role. Now, I look forward to getting out from under the duty of day-to-day operations.” Devellano had practically hand-picked his successor. “We put in this plan three years ago, and Ken Holland becoming the GM is something I’m very excited and very proud about. He’ll probably be around here for another 10 to 15 years.”

That was an understatement. Holland stuck around for 22 seasons, becoming the second-longest tenured NHL general manager. This past May 2019, he handed the reigns over to longtime-captain Steve Yzerman. “The Ilitches offered me a very, very incredible offer to remain with the organization as senior vice president. My thinking at that point in time was that I was going to be a Red Wing for life and work with Steve and support him.” However, plans changed. “I thought I would be there for life, but I also wasn’t sure if I was going to get restless. I told that to Chris Ilitch. I got restless sooner than I thought.” Instead of remaining with Detroit, Holland took a five-year contract for $25 million and full autonomy from the Edmonton Oilers. Holland commented, “I think there is an opportunity here for me to try to make a real positive impact on this franchise.”

Scotty Bowman had been coaching the Red Wings since 1993, after four seasons coaching St. Louis, eight seasons with Montreal, seven seasons with Buffalo, and two seasons in Pittsburg. By that point he already had five championships with the Canadiens (1973, 1976-1979) and one with the Penguins (1992). Bowman also earned the Jack Adams Award in 1977 and 1996. After bringing the Red Wings to the championship in 1997, he signed a two-year contract for just under $1 million per season and agreed to a limited behind-the-bench-only role. Bowman remarked, “This is what’s best for the organization, I believe that. It’s important to keep as many people as possible the same, and that goes for the coaching staff and the players.” Holland agreed, saying, “Scotty is a great coach, and we’ve had a tremendous run of success the last couple of years.”

Other than the five games each coached by his associate coaches, Barry Smith and Dave Lewis (who also signed deals at the same time in 1997), Bowman continued coaching the Red Wings for a total of nine seasons. He led the team to another Stanley Cup in 1998 and then retired once they won again in 2002. As a coach, Bowman holds the most Cups (9), made it to the Final the most times (13), and has the most wins (1,248 in the regular season and 223 in the playoffs). After his coaching career ended, Bowman became the Senior Advisor of Hockey Operations for the Chicago Blackhawks, who then won three Stanley Cup championships (2010, 2013, 2015).

Since 1997, the Red Wings (and thus Holland) have won 10 division championships (1999, 2001-2004, 2006-2009, 2011), five regular-season conference titles (2002, 2004, 2006-2008), and four Presidents’ Trophies (2002, 2004, 2006, 2008). They made the playoffs the first 18 seasons under Holland, ending a 25-season streak, begun in 1991, that stands as the third-longest in NHL history. Of those 18 postseasons, Detroit won the Stanley Cup championships three times (1998, 2002, and 2008) of the four the played. During Holland’s time, Detroit had more victories (1,012) than any other franchise, including 893 during the regular-season and 119 during playoffs.

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