The Edmonton Oilers have a losing culture. They didn’t set out to create one, especially after going to game seven of the 2006 Stanley Cup Finals, but since then this organization has been defined by losing. In 1,032 games played since October, 2006, to now, the Oilers have only won 416. Over 13 years they have won 40% of their games, the worst winning percentage in the NHL.

They desperately want and need that to change, so owner Daryl Katz and CEO Bob Nicholson hired Ken Holland to be the President of Hockey Operations and General Manager and have entrusted him to hopefully return the Oilers to their winning ways.

Becoming a consistent winner isn’t easy, but once you put together the formula you can stay competitive for a decade, sometimes longer. Holland did that with Detroit and I asked him to define a winning culture and how he can he build one here.

He had a long, thorough response.

“That is a great question,” said Holland.

“Ultimately, winning is going to make everything good. Now, how do you start to win? What’s culture? To me, culture is people. It’s the people you bring in on the ice and off the ice.

“They care about the logo, and one of the things I tried to sell as the general manager of the Detroit Red Wings, was that you earn the jersey. You don’t just get to put the jersey on because you were a high draft pick. You have to go to work every day, and respect the jersey and play hard. We (Red Wings) didn’t have a very good year this year, but I think we were involved in almost 50 one goal games, we lost a lot of close games. The team played hard, the young kids were starting to take over the team and we were heading in the right direction.

“At the end of the day, what is culture? It is work ethic, its competing every day. The league is so hard to win you have to compete, your scouts have to compete, your managers have to compete, your coaches have to compete. You’re competing with 30 other organizations which are the best in the world, and you need to grind.

“I guess that is who I am. I love to grind. I love to play golf. I love to get up and down. I don’t want to hit it on the green. I like to get up and down, you know what I mean? I like to get up and down from a bunker. Life is tough, you got to grind, and you have to dig in.

“Right now, times are tough. The team has made the playoffs once in 13 years, and Daryl (Katz) and Bob (Nicholson) have made a decision to bring me in. I have to come in and change the culture and they have given me complete authority to do so.

“I’ve got to provide stability and find the right people, some of them are in this organization, but I may have to go outside and bring some people from outside the organization. That’s the process that I have to go through here and that’s ongoing, so that is what my experience has told me.

“And obviously, you need great players. I had the privilege of working with Steve Yzerman and Nick Lidstrom and Henrik Zetterberg and Pavel Datsyuk. They were great players, and really cared, and I saw when Scotty Bowman came in and how Yzerman became more determined, and he was okay with blocking shots and scoring less points, and winning more draws.

“Young players don’t know that. They want to come in and do what they have always done. There is a process with young players, and you need veterans to show them the way. I’d like to think that’s what I can bring as a veteran manager, hire a coach who I believe is also going to bring that.

“Find the right mix of players to support the core, and create some excitement. We’ve got to get the fans to believe that I’m the right guy, that I can put a plan in place to get them excited.

“There are lots of pieces here. It’s up to me to add to those pieces, to try and figure out the right chemistry, how to support the key pieces that are here through the decisions that we make with players on the ice, and the decisions that I make with the staff,” said Holland.

There was a lot in that response.

I love how he said his scouts, managers and coaches need to compete just as hard as the players. Everyone in the organization needs to have a winning attitude or you won’t win. And earning the jersey is something that has been lacking in Edmonton for a long time.

A few weeks ago at the Alzheimers Faceoff charity tournament I hosted a Hot Stove with Ethan Moreau, Jason Smith and Raffi Torres. Moreau had an interesting take on leadership. He raved about Jason Smith and what he did, but it was more than him.

“Usually you have your main leadership group, but you also have a secondary one, usually the younger players and that was Raffi, Jarrett Stoll and Matt Greene. Looking back, I think the organization undervalued their importance when they traded all of them away. It left a void in the middle of the team. We had older guys and then really young guys. Leadership comes in many forms. When I was young I was more in a lower tier, because I didn’t have enough experience to say things, but being there and showing up every day is important and you bonded with the other young guys because of it. Then as I got older I could be more vocal and take on more of a leadership role. Looking back I think it hurt or organization to lose that second tier group of leaders,” Moreau said.

The Oilers had to give young players bigger roles due to those trades, but they weren’t prepared for it.

We have seen that repeat itself over the past decade, but I suspect that will change under Holland.

He watched the Oilers AHL affiliate Bakersfield Condors win a thrilling 7-6 game in OT last night. He will watch games four and five this weekend as well. Three games are not enough time to make a fair or accurate assessment of a player, but Holland’s track record tells us the Oilers won’t be rushing young players anymore. The young players might not like being demoted to the AHL, but they will be better off for it in the long run and it will make them appreciate being an Oiler more when they make it.

Winning more games will help improve the culture, but in order to win consistently, you need a strong foundation of principles and ideals. Teams who win consistently don’t just stumble into it. They create a stable environment, with strong internal competition and the manager demands a lot of himself, his management team, scouts, coaches, trainers, analytics staff and of course the players.

When one area isn’t held accountable the rest of your organization sees it, and everyone starts to cut corners. It might only be small cuts, but they add up and then you are a losing organization and as the Oilers have proven, it can take a long time to recover.

After last night’s victory, the San Jose Sharks are in the Conference Finals for the fifth time since Doug Wilson took over as GM in May of 2003. In his 15 seasons, the Sharks have had nine 100+ point seasons, 99 twice, and 98 and 96 once. In the lockout season, they had 57 (prorated to 97). They’ve only missed the playoffs once, in 2015.

Their five Conference Finals appearances are tied with Tampa Bay, Pittsburgh and Chicago for the most. Anaheim has had four in the past 15 seasons, while Boston, Detroit, Carolina, Philadelphia and Los Angeles have made three appearances and the New York Rangers, St.Louis Blues, Buffalo Sabres and Montreal Canadiens did it twice.

Teams like Buffalo and Carolina had a few good years, but look at total playoff games played since 2004 and the teams who have regularly been competitive standout.

Pittsburgh 173.
San Jose 168 (and counting).
Detroit 140 (They have had more success in the cap era than many claim).
Boston 135 (and counting).
New York Rangers 129
Chicago and Washington 128
Anaheim 126
Tampa Bay 120.

The Sharks are the only team who haven’t won a Cup, but they have been in the mix consistently, and to me that is a winning culture. Sometimes the difference between winning a series and losing is an unlucky bounce. The Washington Capitals were very good for many years, but they couldn’t get out of the second round. They finally did last year and won the Cup.

Is this the Sharks’ year? We’ll see. Wilson has done an amazing job keeping the Sharks competitive for 15 years. Maybe their window will close, but he has done a remarkable job of re-tooling his roster as his top players get older. He hasn’t been afraid to make bold moves. He’s acquired Joe Thornton, Brent Burns, Erik Karlsson, Martin Jones and Evander Kane as well as other top players, while also drafting and developing Joe Pavelski, Logan Couture, Tomas Hertl, Timo Meier, Kevin Labanc, Marc-Edouard Vlasic and Justin Braun.

He has maintained a top team by developing later round draft picks, and making astute trades.

Holland did that in Detroit and now will try in Edmonton.

Winning is the end result of a good culture, but the philosophy to get there is vital and I’m curious to watch how Holland re-shapes the Oilers culture.