When Henrik Zetterberg’s contract extension came through the NHL’s email alerts back in January of 2009, I distinctly remember clicking on it, looking at the terms, and then immediately looking up his birthday.



October 9, 1980.



That meant that Zetterberg would turn 29 in the first year of his new contract and, more importantly, would turn 40 in the final year of this 12-year commitment by Detroit. I also remember thinking out loud: “This one might sting a little.”



If your job in an NHL front office is to get players signed to contracts (and that was my job in Dallas when the Red Wings did this deal), you walk the fine line between balancing performance value against dead money risk, particularly in a salary cap environment. You also have to walk this tightrope while factoring in external contexts, the most important being where your team sits in its competitive cycle. In other words, you have to balance the needs you know today with...