On Thursday, Sharks GM Doug Wilson will become only the fourth person in NHL history to serve 1,000 games as both a player and a GM. It's a nice milestone but what he really wants is a Stanley Cup.

To give you an idea of how long Doug Wilson has been involved in the NHL, his first roommate on the road was Stan Mikita. One of his first defense partners was Bobby Orr, his first goalie was Tony Esposito and his first coach was Bob Pulford. He was a first-round pick in the World Hockey Association. And in his first draft as the GM of the San Jose Sharks, he took Joe Pavelski in the seventh round.

It has been a long and winding road for Wilson, both as a coach and GM, something he’ll undoubtedly reflect upon Thursday night when his Sharks play at home against the Edmonton Oilers in a game that, for the first time in a decade, has playoff ramifications for both teams. It will be Wilson’s 1,000th game as GM, making him only the fourth person in NHL history to serve 1,000 games as both a player and a GM.

For those of you who don’t remember Wilson’s playing days, he was one heck of a player. When he won the Norris Trophy as the league’s top defenseman in 1981-82, he came within one of hitting the 40-goal mark and hit double figures in goals 13 times during his career. His older brother, Murray, was a worker bee for the Montreal Canadiens and won three Stanley Cups in the 1970s. The admiration Doug Wilson gained for the franchise is something he carries with him now. The Canadiens have always done things the right way, from drafting and developing players to celebrating their stars. Wilson has tried to replicate that philosophy as an executive with the Sharks.

“I’m really lucky to be doing something I love for as long as I have,” Wilson said. “I have a family that, when you think about it, 2,000 games is a lot of road trips, so they’ve supported me in doing what I love. So I think of that. But I also think of all the wonderful people I’ve had the chance to learn from or play with or work with or work for over the years.”

Yes, Wilson feels fortunate. But as they say, you have to be good to be lucky and 1,000 games in both facets is an testament to enduring excellence in both. A lot of guys have played 1,000 games – 306 to be exact – and many of them have been stars and superstars. By the same token, there are a lot of longtime hockey executives, but only three of them before Wilson – Pulford, Bob Clarke and Bob Gainey – have been able to do both play and by a GM for 1,000. There is no real template to becoming a good executive. There have been star players over the years who have been terrible coaches and GMs. And there have been a lot of successful GMs over the years who have had no playing experience. When Jay Feaster led the Tampa Bay Lightning to the Stanley Cup in 2004, he could barely skate and had never played an actual game of hockey at any level.

“For me it’s just a love of the game,” Wilson said. “I love learning every day and I’ve always been curious about learning new things. And I think you can’t be afraid to make mistakes. As a GM, I make more mistakes than anybody in this business, whether it be contracts or trades, but you can’t be afraid to take a swing and you have to learn that mistakes are learning opportunities.”

Wilson is in a pretty good place these days. His Sharks enter Thursday's game holding down first place in the Pacific Division and have won six in a row. If Patrick Marleau has a big night, he could score his 500th career goal the same night Wilson celebrates his milestone. Joe Thornton is eight assists away from 1,000 and the Sharks are coming off their first appearance in the Stanley Cup final. All the while, Wilson has run things pretty well in San Jose, drafting and developing well and making franchise-changing deals for Thornton and Brent Burns. There have been stumbles along the way to be sure. There have been a number of playoff disappointments and Wilson had to fight for his job when the Sharks missed the playoffs in 2014-15, but he made the appropriate changes and got the Sharks to the final.

But he still hasn’t won the big prize. Pulford won four Cups as a player, Gainey won five as a player and one as a GM, and Clarke won two as a player. Wilson is in the Chicago Sports Hall of Fame for his Blackhawk days and his number has been retired by the Ottawa 67’s, but he’s never won the Cup as a player or GM. You’d think that’s what would drive Wilson at this stage of his career and it does, but more than that he wants to keep building something.

“It’s to build a successful organization to compete every year,” Wilson said. “I’m getting better as a GM every day, I hope."

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