Ken Holland’s earliest understanding of the Detroit Red Wings’ organizational dynamic was enhanced by a visual aid. Now the team’s GM, Holland first joined the Wings as a journeyman goalie on a three-week call-up from the American Hockey League in 1983, about one year after local businessman Mike Ilitch had purchased the moribund club for $3 million and the rights he held to three Chuck E. Cheese’s franchises.

Holland quickly got the lay of the land in Detroit, including a strong sense of how much Ilitch was invested in the club beyond his initial stake. A proper owner’s suite was among the many things Joe Louis Arena lacked at the time, so Ilitch viewed the games from a makeshift box that was rolled into the Zamboni entrance. “He was right behind the net, on top of the action,” Holland says.

That level of personal engagement enabled Ilitch to rescue his hometown team from hockey hell and transform it into the NHL’s longest-running success story, with four Stanley Cups since 1997 and 22 consecutive playoff appearances. From the front-line involvement of his family in the early days, to empowering capable people with the authority to make personnel decisions and providing the resources necessary to execute them, Ilitch has worked at every turn to create an environment where winning is the only option.

Jim Devellano likes to joke that, before Ilitch bought the team, the Red Wings weren’t in Detroit—they were in the Detroit River. Devellano was the first employee of the Ilitch era, becoming GM of the Wings in July 1982. In leaving his post as assistant GM of the New York Islanders, Devellano was departing a team that had just won its third consecutive Stanley Cup for a club that came by its “Dead Wings” nickname honestly. “Generally, when you get those opportunities, it’s because the team had been so bad for so long,” Devellano says.

The Red Wings had been in the Norris family since the 1930s and were suffering through a serious losing streak. After dropping the 1966 Cup final to the Montreal Canadiens, Detroit made the playoffs just twice in the next 17 seasons, winning a total of three post-season games. By the early 1980s, the season-ticket base—which included Ilitch—had dwindled to roughly 2,100, and apathy around the team was such that tickets were far more likely to be given away than scalped. “It was worse than an expansion team,” Holland says.

Against that backdrop, Ilitch and his wife, Marian, set about propping up the Red Wings the same way they had built the family’s Little Caesars pizza empire. The first step was installing Devellano as GM. After his initial meeting with Ilitch, Devellano was invited to dinner that night with Marian and the couple’s daughter, Denise. “I got the impression he wanted them to meet me and maybe weigh in on my personality a bit,” Devellano says.

The review must have been positive because the next day, over coffee at the airport, Ilitch offered Devellano a four-year contract. While the new GM’s long-term mandate was building a team from the ground up through the draft, Ilitch needed some instant upgrades within the walls of Joe Louis Arena. “It wasn’t very warm,” Devellano says. “With a bad team and antiseptic arena, the first thing I recall Mike Ilitch doing was really improving the building inside, from the corridors to a new dressing room for the players—making the building upbeat and kind of an enjoyable place to be.”

Nobody was happier inside the arena than the lucky fan who walked away with a brand-new car after every home game, a costly move Ilitch was willing to make if it helped remind people the team existed. Counting the beans all the while was Marian, who basically spent as much time at the rink in those days as Devellano. “She was hands-on and you really needed to be back then because the revenues were not great and the team was not great, so it needed someone to really pay attention to it,” Devellano says.

On the ice, improvements were slow to arrive. Detroit missed the playoffs in year one under the new regime, but walked away from the 1983 draft with Steve Yzerman, Bob Probert, Joey Kocur and Stu Grimson. With a dynamic offensive prospect and a few guys who would fight anyone in the league, the Wings gained some appeal. But in 1985, after losing in the first round of the playoffs for the second consecutive year, Ilitch was getting anxious.

In search of alternative ways to boost the club, he asked Devellano how many undrafted NCAA free agents he thought could play in the league. After consulting with his scouting staff, Devellano estimated there were eight college players who could step into the NHL. Never one to go halfway, Ilitch gave Devellano his marching orders. “He said, ‘I’ll tell you what, Jimmy—sign all eight,’” Devellano recalls.

The flummoxed GM managed to ink six of the players his staff identified, which didn’t endear him to his managerial peers around the NHL because the lucrative offers required to outbid other teams drove up the price for incoming talent. And while the ploy didn’t actually do anything to improve Detroit’s fortunes—the only player who ultimately had a fruitful career was Adam Oates—the spirit of the move was undeniable. “He spent a lot of money when money wasn’t plentiful,” Devellano says. “But what he was trying to do—his heart was in the right place—he was trying to see if we couldn’t accelerate the development of our team.”

While there was no instant panacea for the Wings’ ills, the team did so many things right it was bound to improve. Detroit was one of the first clubs to have faith in Europeans, drafting Nicklas Lidstrom and Sergei Fedorov with the team’s third- and fourth-round picks in 1989. When a high-octane club couldn’t get over the post-season hump in the early 1990s, the Wings went out and hired Scotty Bowman, one of the best bosses a bench ever had. Smaller moves—like giving Larry Murphy a new home when he was booed out of Toronto—also helped the team secure back-to-back championships in 1997 and ’98. After Detroit’s first Cup run, the Carolina Hurricanes tendered Fedorov a massive, front-loaded contract offer. Because Fedorov was a restricted free agent, Detroit had the option to either match the deal or let Fedorov walk in exchange for five compensatory first-round picks. Letting him go would have been a lot easier with one championship in the bag, but Ilitch put up the dough because his hockey operations staff said it was the best move for the team.

Beyond supplying the financial backing to sign players and the open mind to go against league norms, the Ilitch family always maintained healthy working relationships with the people they employ. That’s why Devellano—now Detroit’s senior vice-president—and Holland have remained with the organization for three decades.

“You look at the people who work here; they wouldn’t stay if they had an interfering owner,” says Bob Duff, who’s covered the Wings for more than 20 years for the Windsor Star.

Holland worked as a scout, then assistant GM for more than a decade before becoming Detroit’s GM in 1997. He runs all the big decisions by Ilitch, knowing full well his reasoning will be probed. He also knows how rare it is for someone in his position to have a direct line of communication to the owner, something he cherishes. “I have one call to make,” Holland says.

It’s to the same man who—from occupying a patchwork owner’s box in a barren building, through four Cups and two-plus decades of consecutive playoff appearances—has never stopped investing in the Red Wings.