1. Are there enough weapons around Connor McDavid?
Much like with Jack Eichel and the Buffalo Sabres, the Edmonton Oilers have been guilty of not surrounding their face of the franchise in Connor McDavid with enough quality weapons to truly succeed.
That has been a large factor behind why this franchise has only reached the postseason twice in McDavid’s five years in the league, despite the superstar routinely putting his team on his back and scoring at least 90 points every year apart from his injury-shortened rookie season.
Granted, the arrival of renowned team-builder and architect of the Detroit Red Wings Stanley Cup dynasty, Ken Holland, a year or so ago offered new hope to McDavid, as did the appointment of highly-respected Head Coach Dave Tippett.
And there has been some improvement to the roster this offseason with offensive defenseman Tyson Barrie signed in Free Agency, as was depth center Kyle Turris.
Is it enough though?
Having Leon Draisaitl, who cemented his reputation as arguably the second best player in the NHL behind McDavid with a 110 point season (43 G, 67 A) in 2019-20 certainly helps, but what about the rest of the roster?
Kailer Yamamoto is an intriguing prospect and he could be set for a breakout year on the same line as Draisaitl, while the Oilers will hope that winger Jesse Puljujarvi is motivated to resurrect his NHL career after playing two seasons in Finland following a falling out with the previous regime.
Outside of that, much of the burden will fall on center Ryan Nugent-Hopkins and veteran winger James Neal, but you get the sense that this team needs another legit top-six scoring threat in order to transform the Edmonton Oilers into a genuine cup contender.
And it may have to be something GM Ken Holland considers at the Trade Deadline, or else risk upsetting his most prized asset with another failed season.