Should have signed him after his first year where he struggled for as long a term and as much a cap as it would have taken to convince a first year player who struggled to sign. It was obvious he was going to be at least a Top 4 D in the NHL and a value contract could have been had. I said as such at the time and of course was shouted down for such a "risky" bet on an unproven player as people wanted to wait it out and see, instead of just making the call and going all-in for the savings. This is how value contracts happen, if you believe in the player, sign him before he proves you and everyone right for that belief. And now I await getting attacked by people saying "hOw WoULD yOU KnOw He WOULDA SigneD!?", I think considering his struggles that season, it's likely that with enough money and term he would have jumped at it. It's speculation on my part, but the Oilers never even tried.
With Jones signing a MONSTER contract today, it does not bode well for negotiations with Nurse. It should be considered that Chicago probably did overpay in an attempt to prevent Jones from exploring the market, and they went through years of trying to find and develop good d-men so there was a huge need there. They were also pot committed after bringing in Caleb Jones as well. Needless to say this was a deal and a player Chicago desperately needed and they kind of forced Jones to choose them. With Nurse, I am hoping him wanting be here and wanting to continue with this core helps us to some sort of hometown discount.
Oilers could also help the cause in the upcoming season by making a combination of Bouchard or Barrie (if he resigns) the defacto PP guys. Nurse is not the ideal PP guy anyways, and giving him gravy time on the PP is only going to lead to more production and more $$$. With Bouch and potentially Barrie there is no hockey reason for Nurse to be near the PP.