I would say there is no better time to trade with Edmonton for Nail Yakupov. Their hot seats are scorching now, Dallas Eakins, Kevin Lowe, Craig McTavish, the Artist Formerly Known As The Goof Who Ran/Ruined Columbus, they're all flailing now. Three seasons ago some prognosticators were choosing them as their dark horse to make a run in the West, thinking all that talent had to come together. If anything, they've regressed since then. The season, probably even next season looks bleak.
Nail Yakupov still has all the talent that made some compare him to Pavel Bure. He's still a stocky kid with great gym habits, a very strong lower body and unreal speed. He's just in a very bad situation, in terms of team morale and chemistry, and in terms of the teammates he has to play with. If he'd landed in St-Louis or Dallas there wouldn't be any critics saying he's a wasted pick, he'd have veterans to show him how to be an NHL'er, centres to get him the puck, tough players to insulate him from intimidation attempts, and no-nonsense, established coaches to keep him in line if he does have those prima donna tendencies.
Another consideration is that the Oilers are desperate for quality veterans, which they can't attract in free agency, and are almost impossible to get in trade since the Limited No Trade Clauses that are de rigueur for these same veterans almost always rule out Edmonton as a landing spot. The Oilers are therefore an attractive team to trade with, if you can pull it off, since they're not asking for picks and prospects, but ready-NHL'ers that will enable their young players to thrive. They would like to not waste the window on RNH, Taylor Hall and Jordan Eberle.
The Oilers would have given a lot for Brian Gionta and Josh Gorges, for example, leaders and veterans who work hard and can take over a room, like Andrew Ference can't. We used to laugh at outlandish trade scenarios where we'd rid ourselves of Brian's and Josh's unwieldy contracts and get a young star in return, but with the Oilers in the precarious, peculiar situation they're in, that is precisely what could be engineered if we could get vets to waive NTC's. Except now we don't have these pieces.
We do have two other pieces that I'm sure they'd be interested in: Travis Moen and Lars Eller. Travis, Prairie-boy stalwart that he is, a tough muck and grind player who can 'play the right way' and show the kids how to never stop working, would be a godsend to them, they're famished for that kind of player. Lars, a true centre who is a young veteran now and would fit immediately on their roster as their second-line centre, has the size that make them drool. He would enable the Oilers to send Leon Draisaitl back to junior, which they can't do right now because they don't have any centres beyond Ryan Nugent-Hopkins.
Maybe mix in with a pick and/or prospect, but these two players would be the backbone of a trade the Oilers would definitely consider, in light of the fact that their former #1 overall pick is circling the drain, being wasted. Maybe they need to cash in his value now, before it disappears, even with the awareness that the change of scenery might be all that's needed to unlock all that potential. But that's the situation they're in, they need to make a deal, to prop up their team before it implodes and maybe damages the franchise. So deal they must. Preferably to the Eastern Conference.
One final consideration is that with this little trade scenario we've cooked up, Alex Galchenyuk moves to centre, which we're pretty sure is what we want. It also provides a tangible goal for Nail Yakupov, a chance to play on the wing with the centre he had a lot of success with in Sarnia. Motivation and enthusiasm and reuniting with an old friend and teammate can do a lot to jumpstart a career.
And, we have intel on Mr. Yakupov, by asking Alex and Daddy Galchenyuk what the deal is with the Oilers' right winger. We have instant, deep scouting on him. Is he a great kid in a bad situation? How much effort and resources should we expend to acquire him? If the Galchenyuks are slavering at the thought, we go for it. If they hesitate and equivocate, if they're not sure themselves, maybe that's a good indication that this player isn't the right fit.