This is what makes me a bit skeptical of the hire.
It's fairly unprecedented for an agent to get this job (I know somebody mentioned Burke but still....pretty rare) and it just so happens to be McDavid's agent when McDavid is a few years from free agency. The change is nice as long as Nicholson is out but I question the motive behind this hire, has a nepotistic (if this is a word) feel to it.
a lot of time, moves are made out of opportunity. For instance, a lot of the time when teams poach UFAs from each other, it is divisional rivals doing it. A lot of that is that those teams have been scouting those players for years. Also, often one trade between teams leads to more (ie Calgary and Florida), which would not be the objectively best trades to be made, but it comes from developing a GM to GM relationship
The Oilers have had the chance to deal with Jackson face to face a few times now, yes with McDavid but perhaps more importantly with Connor Brown just now. It could be that he just came of as super well prepared and professional, and maybe had lots of ideas concerning the Oilers even within that Brown negotiation.
I actually supported Katz hiring Nicholson for the same reason. Katz is just a businessman. There would be little chance he knew anyone in hockey, and could not even begin to hire anyone as he just didn't have the knowledge. So, of course he would have to start things off by leaning on Lowe, and Nicholson was great because it was an outside hire who had tons of connections and knew a lot of team and player information. Plus, he has hockey knowledge. Moving on from Nicholson wouldn't be easy. I'd imagine the next order of business for Jackson is for him to see how Holland operates and make a decision about whether or not to move on from him, and if Staios is truly a great choice to take over.