
When NHL insider Elliotte Friedman speculated “there’s something imperfect" in Connor McDavid's eyes, and that's why he hasn't signed an extension in Edmonton yet, fans started wondering what exactly that meant.
Friedman added, “McDavid must be convinced the Oilers will continue to be a serious Stanley Cup contender.”
So what does that mean? Is a trade necessary to convince the superstar this Edmonton Oilers roster is better than one that has been to two straight Stanley Cup Finals? Do they need to sign someone else to a longer-term deal that McDavid sees as part of the roster over the next few seasons? Is there someone in Edmonton that McDavid doesn't feel is pulling his weight?
Analysts and insiders have been guessing at the reasoning behind McDavid's willingness to wait. What was thought to be a 'done deal' has now become a bit more worrying, many thinking there's not much the Oilers can do to get better. It may be especially challenging to add someone that helps this season and next...
Any move likely starts by letting someone on the current roster go.
Oilers Potential New Goalie PTO Target
Oilers Goalie Revenge Tour Begins Now
How Much Is Connor McDavid Worth?
Most people believe that the Edmonton Oilers need an upgrade in their goaltending. That will lead to speculation that goaltender Stuart Skinner is not the solution. However, trading Skinner comes with serious risks. Is there an upgrade available on the market that the Edmonton Oilers can acquire that would appease Connor McDavid, assuming he's worried the goaltending is not up to par?
Options on the trade market and in free agency are limited. Assuming that someone like Ilya Samsonov on a PTO would be enough to satisfy me David seems illogical. Even John Gibson, who was traded to the Detroit Red Wings, wasn't viewed as an upgrade by everyone. The Oilers have missed the boat on that one, assuming they were looking at Gibson to begin with.
Nico Daws and Michael DiPietro could be options, but would McDavid feel more confident with either over the Oilers' current tandem?

Do the Oilers take a chance and move someone like Stewart, or Calvin Pickard, consulting McDavid and asking if the goaltender they're looking at acquiring would appease his concerns about how solid the team is in net?
Oilers Goalie Revenge Tour Begins Now
EDMONTON – <a href="https://thehockeynews.com/nhl/edmonton-oilers/latest-news/oilers-stuart-skinner-5-potential-trade-destinations">Stuart Skinner</a> is used to the doubters.
The Oilers made a conscious decision this offseason to go with youth and speed over aging veteran experience. That will allow someone like Matthew Savoie, who could come into camp and start the season on a roll in the Oilers' top six.
However, Savoie may not produce much of anything at all while he makes the transition to the NHL. How comfortable does that make someone like McDavid, who for years has watched as the Oilers have struggled to land a top-six winger who has consistent scoring ability?
Perhaps, McDavid is looking more at the need for a guarantee in that spot than a rookie who, while his ceiling is high, could fall flat on his face. Do the Oilers then dangle someone young with a high ceiling to a team that has a player the Oilers could use now with a proven track record of results?
Such a move would see the Oilers abandon their pivot towards youth, which could be counterproductive to their long-term success. Yes, potentially moving Savoie now could help the season but if McDavid is concerned about what the long-term prognosis is for this Oilers roster, someone like Savoie could be critical over the next few seasons.
Trading players like Mattias Janmark, Ty Emberson, or Kasperi Kapanen may not move the needle for the Oilers. At the same time their small contracts when added up (over $3 million) and moved could mean a potential bigger addition for Edmonton.
What could the Oilers do with that $3 million? Does that allow them to add a goalie that McDavid feels more comfortable in? Could they acquire a forward with a few years of NHL experience that has a solid chance to take a bigger step over the next year or two?
These three players are useful. But, if there's one thing the Oilers have learned over the previous two seasons, it is that there is little to no margin for error. Anyone not pulling their weight needs to go. All have played a more minor role on a team that needs difference-makers to get past a club like the Florida Panthers.
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