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Pittsburgh Penguins' Sidney Crosby during an NHL game against the New York Islanders in Elmont, N.Y. on April 17.Seth Wenig/The Associated Press

The last time Sidney Crosby signed an US$8.7-million-buck-a-year deal, it was a headline with a question mark at the end of it.

This was the same annual salary he’d been paid on his previous deal. Since then, Pittsburgh had won a Stanley Cup. The number no longer made Crosby the highest paid player on his own team, never mind the league.

But according to then-Pittsburgh GM Ray Shero, Crosby worried that if he asked for too much money, he wouldn’t get what he actually wanted.

“He came back … and just said, ‘This is really what I want to help out the team,’” Shero said back then, in 2012.

Crosby and the Penguins won two more Cups and everyone was happy.

With his history of concussions, most people didn’t expect Crosby to last the 12 years the deal ran, but here he is. He’s no longer the best player in the game, but he’s still up there.

If you needed one guy for one game, he still might be the player most coaches would choose. Without him, Pittsburgh has no chance and, worse, no glamour.

You could make an argument that, however rich he is, Crosby is still owed by Pittsburgh. Most agents would.

That is close to an unassailable bargaining position.

So what did Crosby do on Monday? He took another submarket deal. Once again, he will be paid US$8.7-million per year. This time, the extension runs two years.

Think of how Crosby might have played this.

He could’ve strung out negotiations for the whole year. He could’ve dropped a couple of hints about an organization on the edge at some tenuous moment in the season. He could’ve sown chaos with small gestures on the bench or in scrums.

Then he could have left next summer. If he was feeling especially vengeful, to a contender offering even less money.

It would have ruined the Penguins’ ‘organization that does things the right way’ reputation, and moved forward the Doomsday Clock of every executive currently working in Pittsburgh.

Instead, Crosby took a figurative knee. It’s not the money so much as the term. What veteran star with leverage signs a two-year deal?

By the time the extension ends, Crosby will be looking over the fence at 40. At that point, he’s into his good-in-the-room phase. He’s given up 20 or 30 million dollars here. More even. It’s mad money for a quarterback, but still enough to matter to a hockey player.

It’s easy to get carried away with this line of argument. What Crosby’s done is not selfless. Selfless would be taking that $8.7-million and giving most of it away. But it shows that Crosby values something more than financial superlatives. He would rather be thought of as a team guy than live as a fractionally richer one.

Every NHL executive is looking for the next Crosby. Monday’s decision demonstrates how that’s a twofold search.

The easy part is finding a guy who plays like Crosby. ‘Easy’ in the sense that when someone comes along who is this talented, spotting them does not a take a lifetime of training. Then the job is angling your franchise so that it has a decent chance to draft that guy and build around him.

Players like that arrive once every couple, three years. It takes them a few years to get settled. You have to hope they enjoy pressure, aren’t driven bananas by money and/or fame and are resilient as well as gifted. Lot of ifs.

Then the second part – the really hard part – of the search starts.

How do you get a guy who’s as good as Crosby, who also wants to win as much as Crosby? Who is obsessed to the point of fixation with being perceived as ‘playing the game the right way?’ Who is the guy whose hand shoots up straight away when someone says, ‘Okay, I need a volunteer to …?’

Every player says they want to win. The better they are, the more opportunities they have to say it. All of them undoubtedly do, but they would also like to make more money than everyone else. The two things don’t necessarily go together. In a salary cap world, they are often in direct opposition.

The Toronto Maple Leafs problem isn’t finding talent. It’s that the talent they’ve found is shameless, and keeps mugging them.

It is not wrong for an athlete to pursue money, in the same way that it is not wrong for any one of us to do so. The only people who think money isn’t important are people who have more of it than they need.

But the athlete you want on your team is the guy who doesn’t think like everyone else. He wants money, yes, but he wants winning and legacy more. He has the ability to imagine himself 30 years into the future. What will matter then?

The only way to know if you have staked your own future on this sort of player is to get him a few years into his professional career and see what he does. No one since Crosby has handled this the way Crosby has.

Plenty of guys who are somewhere between okay and pretty good have taken less than market value to play somewhere they like. Many veterans have given club discounts to grab a chance at winning late.

But there is no superstar-level hockey player who has done two sweetheart deals in a row for a club that established a dynasty around him.

This time, it will cost Crosby a fourth or fifth luxury property. Maybe he’ll have to finance that yacht he probably doesn’t want.

But when he’s 60 and people talk about him, they’ll do it in terms reserved for someone like Jean Beliveau: a guy who didn’t just change the game, but venerated it so much that he put it at the centre of all his dealings. Someone who never took a wrong step in public. Someone who told you what mattered to him, and then backed up words with actions.

If you want to win in the NHL, the easiest way to do that is with a Sidney Crosby. Unfortunately, they’re not making any more of him.

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