The Chicago Blackhawks have a problem that most general managers in the NHL would love to have: How to keep their two best players under contract long-term? Both Toews and Kane are reportedly looking for upwards of $10 million per season, so how does Chicago make this work?

Don’t expect a pity party for Stan Bowman as he attempts to maneuver pieces to keep Jonathan Toews and Patrick Kane in a Blackhawks’ sweater. The Hawks have been at or near the top since the dynamic duo first joined forces in 2007, winning two Stanley Cups and terrorizing the Western Conference.

The co-Calder Trophy finalists introduced a new era in Chicago that corresponded with Rocky Wirtz taking over the franchise. After suffering under the despotic rule of Rocky’s penny-pinching father Bill Wirtz, the Hawks became more fan friendly and the model organization for the rest of the NHL.

The problem with growing your team organically is that players eventually outgrow their contracts and possibly the spending limits of their team or in some cases, the salary cap. The Hawks have reached that point this season. With both Kane and Toews beginning the final year of matching five-year $31.5 million deals, the time has come to seriously readdress the makeup of the Chicago roster.

In theory, the Hawks have until June 30, 2015 to address their roster plight, but there is no way that Chicago ownership lets either star get within six months of the open free agent market. According to Capgeek.com the Hawks are already in the red by $2 million so they will need to make a move before the season starts or suffer financial penalties.

With their two biggest stars on the line Chicago will certainly not take any risks with the salary cap and are more than likely to prey on a team in need to dump some salary. The Hawks have 23 players under contract with several youngsters looking to move up from the AHL (Adam Clendening, Drew LeBlanc, Stephen Johns and Ryan Hartman).

The faith in the youth of Chicago will be put to the test because some roster spots will be opening as the Hawks will go into salary dump mode soon after the face(s) of the franchise get their monster deals.

Kris Versteeg ($2.2 million cap hit) is probably the most obvious trading piece, but there have been whispers that Patrick Sharp ($5.9 million cap hit) could also be on the block.  On the blue line don’t expect any of the bigger names to be available, but Niklas Hjalmarsson and his $4.1 million cap hit could be dealt. Marian Hossa’s contract is ridiculous and makes him almost impossible to move.

What it boils down to is that Chicago has put the equivalent of a franchise tag on two of the best young players in the NHL. They will sign them to enormous long-term deals that will lock them in place, render them untradeable, and effectively remove Chicago from any free agent activity.  As smart as Chicago has looked accumulating talent, they are getting ready to cripple themselves for the next decade.