Last season, Oscar Klefbom established himself as a key building block in the Oilers’ defensive plans. He has one year remaining on his entry-level deal and will become a restricted free agent next summer. When should Edmonton extend him, and what kind of deal should they offer him?

Almost as critical as the kind of deal Klefbom signs is the exact timing of his extension.

Edmonton could choose to sign Klefbom immediately. There are a number of advantages to doing so. One of the most obvious is that teams are fighting through a cap crunch right now, which means that it’s a little easier to get that contract down into a reasonable dollar range. Another is that with just a single full NHL season under his belt, Klefbom doesn’t have much of a track record to negotiate with.

The primary appeal of waiting until either some point into 2015-16 or even the very end of the season is the chance to gather more data. Peter Chiarelli might prefer to see the player for a few months before making such a big decision. The Oilers might prefer another full season of data, just to make sure Klefbom doesn’t stumble in his sophomore campaign.

There’s also the option of not signing him at all, instead deciding to ship him off somewhere else. Given that he’s a 6’3”, 210-pound defenceman with a varied skillset, and that at 22 years old he fits the Connor McDavid window pretty much perfectly, it’s my view that only a crazy person would do this.

Once the decision to sign Klefbom has been made, the next question is how long should the Oilers extend him for?

One-year deal. These are pretty rare for defencemen who play significant minutes in the NHL during their entry-level deals; typically these instead go to players who need to prove that they’re full-time major-leaguers. Nevertheless, this is one possibility, and if Edmonton wants to be absolutely sure of what it has they could push for this.

The bridge deal. These much-maligned two-to-three year contracts can work in some situations. They give the team and player time to assess fit, generally resulting in a third contract which accurately captures the player’s value (while at the same time ending prior to unrestricted free agency, allowing the team to retain control). They don’t cost very much; for a player like Klefbom something in the $2.5 million/season range seems plausible. For a club with cap issues and/or a level of uncertainty about the player, this can be a good option.

The long-term extension. This is the big gamble, and one we’ve seen with increasing frequency from NHL teams. The primary downside is that if a player doesn’t develop as expected these deals can be a real pain; players like Luke Schenn and Jared Cowen have become cap headaches for their respective clubs. There are other points worth worrying about, too. These deals tend to be more expensive as both sides calculate in development, which can create cap problems. More paternalistic types also tend to worry about showering a young man with this kind of money at such a tender age. Finally, when these deals expire the player is an unrestricted free agent.

The upside is that when they work they work brilliantly. Players like Jonas Brodin, Roman Josi, Travis Hamonic and John Carlson are all inked long-term in the $4.0 million range; all are significant bargains for their respective NHL teams. In exchange for giving these players money and term, their teams now have high-end defencemen locked up at a comparative bargain for years to come.

In Chiarelli’s shoes, I’d probably wait until November, and if Klefbom continues as he’s started I’d sign him for as long as possible. Cap pressures are already a bit of a concern, and two-to-three years from now they could be really bad; if this team develops as hoped, having Klefbom signed long-term at a reasonable dollar figure could go a long way towards keeping Edmonton’s core together.

As always, though, the final word in WWYDW goes to the comments section. In Chiarelli’s shoes, when would you sign him, and what kind of deal would you hope to negotiate?