So realistically, for the Oilers to go on a Stanley Cup run you would have to start with the team gelling and rolling like it was last year at its peak, and then improve on that. The PP and PK would need to continue to be tops in the league which could happen given there hasn't been much change to those units personnel-wise. However, Klefbom is on LTIR and played important minutes in all situations, so without your #1 is that even possible? How do you make up for that loss? The goaltending has been inconsistent as has forward production and defensive play as a team.
On D with the current roster you don't have any potential #1, so most importantly you would need Nurse and Bear playing at a higher level than last year which is possible. Bear would need to take another step offensively and improve his defensive coverage and gap control, and Nurse would need to cut down on his mistakes and be more discerning in his decision making when breaking the puck out, either in passing to teammates or carrying the puck through to the offensive zone and making a better play once he's entered the zone. Barrie would need to be better which he obviously can be. Hopefully his start can be chalked up to him still settling in with a new team after a long layoff and he can go back to being productive offensively, he probably just needs to get his confidence up. Barrie would also need to develop chemistry with a D partner as well. Larsson would need to play like he was playing towards the end of last season where he was defensively shutting other teams down efficiently. Jones would need to take a step and become a top 4 two-way player. Koekkoek has generally been better than expected and built on his play at the end of last season with Chicago, so if he can continue to build on that and be a solid contributor then that's found money. Russell would need to...be a better starfish?...Not sure this cowboy is learning any new tricks so he would just need to be his best penalty killing self when in the lineup. If Lagesson and Bouchard could step in when an opportunity arises and displace another defenceman because their strong play offers more than an incumbent's that would also be a positive. So essentially the answer to no Klefbom is improvement by committee, especially defensively and in transition.
In goal it's pretty simple. Koskinen and/or Smith when he's back would need to go on a heater(s) and steal some games.
At forward, the best line we saw last year was the DRY line so obviously put them back together. Aside from that you need some players to gel with McDavid, and at this point just try Pulju there. They seemed to generate offense at the end of the game last night. Based on Pulju's start to the season I think at worst they would be a pain in the ass possession-wise for other teams. Put Neal with them and see what happens. If Neal and Pulju are digging pucks out for McDavid and taking the puck to the net it should create chaos that McDavid can take advantage of. Or Maybe Kahun with McDavid and Pulju ends up having some chemistry. If that line works and is outscoring the opposition, and the DRY line is back doing its thing you're off to the races. For the bottom-6 if you put Kassian with Archibald and Shore and told them to dump the puck in and go hit the defenceman they could be an effective checking line and all of those guys have the ability to chip in and bring some energy. Then if the 4th line (whoever makes a good combination out of the remaining forwards) could go out and be an even +/- group and chip in a goal every few games that would give the Oilers a bottom 6 with some identity that can contribute 5 on 5. Does this roster have 3 players to make up a satisfactory 4th line that can hold its own? Maybe Ennis-Turris-Chiasson could work but all 3 would need to regain their past form. Ennis broke his leg so maybe he just needs a bit more time to get back to form, and maybe once Turris is settled he'll look better too. Chiasson contributes when he's on. Nygard is another guy who looked good in his last game, looks more comfortable skill and position-wise than last year, so maybe he could come in and be a positive contributor in the bottom 6 too. The other bottom 6 possibility that looked good in the play-ins against Chicago was Neal-Khaira-Chiasson, so if that line could go out and be a positive difference maker that would be huge too.
So it is possible if things go right, if players progress and things click chemistry-wise for the Oilers to be good in net, solid on defence and dynamic on offence. However Tippett has gotten in the way by being reluctant to try seemingly obvious line combinations or to go back to certain successful combinations. The systems play has also looked too passive for the way the game is played in today's NHL, especially in the defensive end, and the team looks easily disjointed positionally in all zones on a regular basis rather than consistently working as a 5 man unit which if it's happening with all of the lines seems like a systemic issue. The Oilers' issues clearly don't just boil down to repeated individual poor decisions by players, poor hockey IQ, or a lack of skill. Which brings me to another question....
Can the Oilers win the Cup with Tippett calling the shots behind the bench? Because there are some troubling tendencies from the coach which seem like they're limiting individual player and team progress rather than the coach elevating the team with an effective system that plays to its players' strengths. Is Tippett the only problem? Clearly not, and yes the roster could be significantly better. However it's also clear that the roster is not the only thing that is lacking.