After thinking about the situation more part of me thinks Jackson was aware this offer sheet situation could happen and some of his actions make sense. For example signing all of Skinner, Arvidsson, Henrique as well as Perry, Stetcher, Brown. It seemed like a lot at the time but if he felt like someone was going to pull a move and put them in a position to have to overpay on question mark young players it makes sense sense that he would bring in more free agents to mitigate the possible loss. Then he went out and shed salary while also bringing in cheap young players who could be close to ready in Savoie and Jarventie.
Then I look at it from Broberg and Holloways agents point of view. Neither of them likely wanted to negotiate mid season when their clients are struggling to even be in the lineup and contracts aren’t getting negotiated during a playoff run so you get to the end of the playoffs which is a week before free agency. At that point they would have known at least one GM in Armstrong is looking at offer sheets (he had stated as much) and the agents would have known Edmonton was extremely vulnerable so what’s the point of advising your client to extend with the Oilers at that point? Why not just wait until free agency starts to see if any GM’s reach out.
I can see a situation where both agents were hesitant to sign a new deal with Edmonton before free agency started in order to see if an offer sheet comes. It’s not like they have anything to lose by waiting, as it wouldn’t change their negotiating position with Edmonton. If Jackson felt like this is what was going on then it makes sense that he went out and signed all these players on day one of free agency as an insurance policy in anticipation of Holloway and Broberg being offered contracts that would be tough to match.