What should a Sidney Crosby contract extension look like?

How much money? How many years?

With more information trickling out by the day that Pittsburgh Penguins captain Sidney Crosby, who turns 37 in August, is closing in on his fourth, and likely final, NHL contract, that got me thinking: What should this contract look like?

Given that Sidney Crosby has taken very generous hometown discounts throughout his time as a Penguin to allow the team to be more competitive, would logic and history indicate another team-friendly deal is on the horizon?

Cole Harbour’s favorite son has signed three contracts throughout his 20 seasons in the National Hockey League, per CapFriendly:

• Sep. 5, 2005 - a three-year entry-level deal worth $11.1 million
• July 7, 2007 - a five-year deal worth $43.5 million
• July 1, 2012 - a 12-year deal worth $104.4 million

Since the beginning of the 2008-09 season, Crosby has purposely and superstitiously maintained a cap hit and annual average salary of $8.7 million.

Would Sidney Crosby agree to a, let’s say, three-year extension totaling 26.1 million ($8.7 million cap hit per season)? Will Crosby go beyond the widely suggested three-year range, playing past his 40th birthday?

Or, because the salary cap is rapidly increasing now, should No. 87 take a bigger piece of the pie? Who could say no to Crosby for wanting a bit more moolah on the back nine? He’s certainly deserving of a raise if he requests it.

What about a three-year deal with a cap hit of $10.87 million per season? Is that too rich for you? $10,000,087? That 87 figure is getting in there somewhere.

One thing is certain in all of this contract speculation: I’m willing to bet my grandma that Sidney Crosby will finish his career with the only NHL team he’s ever known (sorry, Colorado and [insert Canadian NHL market here]).

Here’s how I would do business in this instance.