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The Stanley Cup GMs: Ken Holland, Bill Zito and two paths to the finals

SUNRISE, Fla. – It’s killing Jim Nill not to be here for the Stanley Cup Final. Because he certainly had the team to do it.

But when the general manager of the Dallas Stars visited his old friend Ken Holland on Sunday night after the Western Conference finals, no matter how painful and raw the loss was at the time, another thought occurred to him.

“If I were to lose, I would want to lose to Kenny,” said the ever-stylish Nill The Athletics Thursday by phone. “I’m happy for him, for his career, for what he’s done and what he’s built in Edmonton. He did a great job. He built it the right way. And in a high-pressure environment, he stuck to his guns. That’s what I love, what he believes in.

‘He’s done the right things. And now the organization in Edmonton is reaping the benefits.”

There is an elephant in the room, not that it is a secret, when it comes to the Netherlands in this Stanley Cup final. His five-year contract as Oilers GM expires June 30. Beyond that, his future is unknown, and he definitely doesn’t want that to become a topic of conversation or a distraction in the coming weeks.

But in the hockey world, there is some real luck for a man as popular as he is within the GM ranks to have gotten the Oilers over the hump and into the Cup finals.

Bill Zito’s eyes lit up Friday during his Media Day press conference when he was asked about his GM counterpart.

“Nothing but complete admiration and respect, both as a hockey man and as a person,” the Panthers president of hockey operations and GM said of Holland. “Even when I was a cop, you could visit Kenny and talk hockey, and he would help and give you guidance. You would be talking about players. I got a chance to do some USA Hockey stuff at the World Cup, and he was there with advice. Just nothing but sincere admiration and appreciation.

‘And I know I’m not the only one. I know all the people in hockey he helped. Great guy.”

Steve Yzerman, of course, got his start in management under Holland in the Red Wings front office.

“Kenny has done a tremendous job putting together a team that will compete for the Stanley Cup,” said the Red Wings GM and Hall of Fame player. The Athletics via text Friday. “His teams have made the playoffs every year he has been in Edmonton, which is an extremely difficult feat in this league. He has shown that he is not afraid to make bold moves, several of which have had a positive impact on the current team and are a major reason the Oilers are in this position today.”

Nill, who played junior hockey with Holland, also cut his teeth in management under Holland in Detroit.

“I was very fortunate to work under Kenny – first as head scout and then as assistant GM,” Nill said. “He became one of my mentors. A lot of what I learned in the game I owe to Kenny. From scouting to the management part, managing people, I owe a lot to Kenny.”

The hockey world is quite small in many ways. So many connected layers. And just as fascinating is playing the game What If?

Five years ago, when then-Oilers CEO Bob Nicholson conducted a lengthy and exhaustive search for GM, he was extremely impressed by his interview with Zito, then the assistant GM in Columbus.

“He was really good,” said Nicholson, now a senior advisor at OEG The Athletics Thursday by phone. “I interviewed a lot of people and he was definitely in the top, last group. And then Kenny became available and we went that way. But look at what Bill has done, from being a player agent to working in the American Hockey League, he had done every part of the hockey business.

“And went into that in more detail. And analytics started to become bigger and bigger, and he was certainly one of the leading candidates in that area. It didn’t work for him with us, but you knew he was going to get a job as GM. It was just a matter of when and where, and it wasn’t long after he was hired in Florida.

Zito fondly remembers that 2019 interview with Nicholson.

“We met early in the morning in Toronto at the airport,” Zito said The Athletics on Friday. “I think he told me it would take an hour and a half, maybe two hours. “So take your flight back at noon.” We were talking about hockey. We decided to get something to eat. I kept changing my flight. I finally went home around 6pm

“Anyone who has been lucky enough to talk hockey with Bob Nicholson, it was great. I remember thinking what a great guy he was. He was the kind of guy who would ask a question and I would give an answer, and his next question would be based on what you said. I really got the feeling that he was interested in what I had to say and wanted to get to know me.”

Everything happens for a reason, and the reality is that Holland coming to Edmonton and Zito getting his first GM job in Florida a year later in 2020 probably worked out for the better for everyone involved.

Zito has been able to develop his skills as a first-time GM under much less supervision and attention in South Florida on his way to building a strong Cup contender. I don’t think the pressure cooker in Edmonton in 2019 was a job suitable for an entry-level GM. There was so much toxicity in that market at the time.

“There’s something in the water here in Edmonton that we don’t have right, and we need to figure it out,” Nicholson said quite famously at the January 2019 press conference announcing the resignation of Peter Chiarelli as general manager.

No, that wasn’t the time for a rookie GM.

Nicholson was absolutely right to bring in a four-time Cup champion GM from Detroit to handle that task. Not that it hasn’t had its ups and downs. The glare was intense.

I asked Holland on Friday if he had ever wondered during the bad times of the last five years why on earth he took the job at Oilers GM.

“No, I enjoyed every moment of it,” Holland said without hesitation. “The National Hockey League is a roller coaster ride. If you think you can only get to the top and sail at the top, you should start another company. Because I will advise you right away, you are in the wrong business. Because there will be lows and there will be highs. We’re in this business for the highs, but you have to have a thick skin for the lows.

“If you make ten decisions, you have to make seven or eight good ones; one or two or three won’t work, and you hope they’re not too bad.”

Certainly, the signing of Jack Campbell has been an unmitigated disaster. But the addition of Zach Hyman this same offseason may be the best unrestricted free agent signing in the NHL in the last decade. Trading for a tough defenseman like Mattias Ekholm before last season’s trade deadline was extremely smart. Even the smaller deals, like bringing in Brett Kulak from Montreal.

When a 2-9-1 start in November forces a coaching change and everyone goes crazy in Edmonton, it feels like a low point. But the Netherlands trusted that the Oilers would turn the tide. And when he looks back on these five years, he feels fortunate for the experience in hockey-crazy Edmonton.

“I love the passion,” Holland said. “I have been fortunate to work at two franchises in Detroit and now in Edmonton, which have great fan bases. That’s why you come to the ice rink. Because what you do is important to people. Especially in Edmonton, what we do every day, what the players do, is important to those fans, to that city. And you know if you’re 2-9-1, they’re not happy, we’re not happy. …

“But it’s been an incredible run and I’m happy to have this opportunity.”

(Top Photos of Ken Holland and Bill Zito: Dave Sandford and Bruce Bennett / Getty Images)

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