Jonathan Willis has a great piece at Bleacher Report today about the Chicago Blackhawks and the tough situation in which they find themselves following long extensions to Patrick Kane and Jonathan Toews, a number of other wealthy contracts, and the fact that the salary cap is unlikely to rise as much as originally hoped. This type of situation is, of course, the result of success, as GM Stan Bowman has had to pay his players high salaries thanks to the free agent demand for players who are well-developed, put in appropriate roles, and showcase their talents in the playoffs.

Here is the chart from the article, which shows the players the Hawks have under contract, with only approximately $8 million in cap space left.

The situation is interesting to me because here we have a great team that is forced to make a lot of moves to attempt to remain competitive. This isn’t a situation we see that much in hockey – generally the bad teams try and make moves, the good teams only try to get incrementally better, since they are…well…already good, and because they don’t want to break up any supposed dressing room chemistry. But the first thing Stan Bowman’s dilemma reminds me of is the situation in Oakland with Billy Beane and the Athletics. Of course there are differences – Beane is fighting a budget, Bowman a salary cap – but the idea is similar. Going into the 2014 offseason for Beane, and the 2015 offseason for Bowman, both GMs did/will face the task of remaining competitive while cutting salary. It’s a tough situation, made more difficult when opposing managers know the hardships you face, but it is also an incredible opportunity. If I were Bowman, I wouldn’t be dreading the coming offseason. Instead, I’d be waking up every morning and thinking outside the box. “What can we do to cut salary and still extend our window?”

The biggest example of such thinking thus far in the NHL has been with the Philadelphia Flyers traded stars Mike Richards and Jeff Carter in the same day in order to get younger, free up cap space, and to an extent change the culture (we won’t discuss Ilya Bryzgalov here because it’s not relevant but obviously that signing sabotaged those efforts). So what can Bowman do along those same lines to get younger, extend his window, but still cut salary and potentially improve?

In this case, it won’t start with the stars; Jonathan Toews and Patrick Kane are not going anywhere. They’re still fairly young, are outstanding players, have no character issues at this point, and there’s no Claude Giroux behind them to pick up the mantle once they’re gone. So one must look beyond that.

My first move would have come prior to the season. Recognizing Nick Leddy to be a future top pairing defenseman using analytic research, and identifying his puck moving abilities as being especially useful in the evolving NHL, I would have signed him to an RFA extension; think of the Roman Josi contract as an example of the type of structure I would seek. In order to clear cap space, I would have traded Patrick Sharp. Of course, none of this did happen, but that likely would have helped with the retooling.

I wrote a piece early on this year about how the Chicago Cubs are targeting young, drafted pitchers once they had developed just enough to get past the stage in which they were likely to bust. The idea was that a similar tact could be taken with defensemen in hockey. There are still guys out there who fit the criteria and could help a retooling team with a low salary, and I would target those guys. Patrick Sharp, Brent Seabrook, Marcus Kruger, Bryan Bickell would all be traded for younger players under team control for longer, with the ability to replace them if not next year then in the near future.

The idea would be to remain competitive next season, at least as competitive as the team would be using a conventional approach to staying under the salary cap under such conditions, but that in two years, rather than fall off the map, the team would return to the top of the standings (think Red Wings of last year versus this year, just in terms of placement).

Understanding the cyclical nature of contender status in hockey is vital to retooling. Sure, technically anybody can win who makes the playoffs, but the probabilities are stacked against a team that tries to hold on another few years with a declining core that can only get worse. Creativity is necessary to turn a contending team into a true dynasty in a salary cap world.