Over the past few days, I’ve taken a look at the two most important things on Ken Holland’s to-do list this off-season.

First, there’s the most glaring need — another goaltender. Mike Smith had nice flashes this season, but the Oilers ultimately need an upgrade to split the need with Mikko Koskinen in order to be a serious contender.

Second, there’s another critical need — a third-line centre. Riley Sheahan was a key part of Edmonton’s great penalty kill, but the Oilers’ third line got carved up at even-strength with him as the pivot. Holland needs to find somebody capable of driving a strong third line that can break even with opponents.

Now, finally, there’s one more hole to look at — another top-six winger to play alongside Connor McDavid. While Zack Kassian has found himself a home alongside McDavid, the captain had a revolving door or players on his left side.

When the Oilers got rolling this season, a big part of it had to do with the stellar play of the Leon Draisaitl, Kailer Yamamoto, and Ryan Nugent-Hopkins trio. As great as that line was, though, it pretty much left McDavid by himself. The Draisaitl, Yamamoto, RNH trio had an insane 28-to-8 goal differential when playing together this season. Meanwhile, once that trio was put together, McDavid just broke even in terms of five-on-five goal differential at 20-to-20.

Given his tendency to generate offence through big, one-off plays and rushes, it’s important for McDavid to have quality two-way players on his wings. This is why Nugent-Hopkins was put on McDavid’s line in the playoffs, to give him not only a quality skilled player in the offensive zone who can keep up and score, but also to have a defensively-responsible veteran who can compensate when McDavid goes all-in.

As nice of a fit as Nugent-Hopkins is on McDavid’s wing, using him there might not be the right play. For starters, the trio of Draisaitl, Yamamoto, and Nugent-Hopkins is so good that it’s difficult to consider splitting it up being a net positive for the team. Beyond that, as I mentioned in my third-line centre post, given the ho-hum market for quality centre upgrades, Nugent-Hopkins might be the best option for the Oilers to put together a good third line. So, if you’re going to move Nugent-Hopkins off of that great trio, using him as the third centre would probably be the most worthwhile move.

So, who should McDavid’s wingers be? Is there a fit to be found on the open market or via trade? Or might the ideal fit be internal?

I’ll start off by saying that the Taylor Hall Redemption Tour isn’t going to happen. There’s just no way that the Oilers can make it work financially given where the salary cap is at right now. In the same vein, bringing in a high-scoring name like Mike Hoffman isn’t going to happen either, unfortunately.

If Tyler Toffoli doesn’t re-sign in Vancouver and reaches the free-agent market, he could make some sense as a fit. Toffoli is coming off of a nice rebound season in which he scored 24 goals in 68 games between L.A. and Vancouver. He has Stanley Cup pedigree and plays a fair two-way game.

That said, Toffoli is a right-winger, which isn’t quite as much of a need up front for the Oilers. They already have Zack Kassian, who was given a handsome extension due largely to his chemistry with the captain, Kailer Yamamoto, Josh Archibald, Alex Chiasson, and maybe Jesse Puljujarvi on the right side. It’s more worthwhile to focus on left-wingers.

A name I mentioned when I talked about centres who could be a nice fit is Mikael Granlund. Granlund is listed as a centre and spent his early career as a pivot, but he’s played mostly the wing (both left and right, though he’s a left shot) over the past few seasons.

Granlund didn’t work out too well in Nashville as he scored just 35 points in 79 games after being acquired at the 2019 trade deadline. But his underlying numbers were very good this season and he isn’t far removed from 67- and 69-point showings in Minnesota. Granlund has great skill and plays a very solid defensive game.

Another interesting name on the free-agent market is Erik Haula. After a breakout 55-point season with the Golden Knights in 2017-18, Haula got injured and missed most of 2018-19. He ended up getting dealt to Calrolina as a cap dump and then got flipped to Florida at the trade deadline. All told, Haula scored 24 points in 48 games between the Hurricanes and Panthers.

He isn’t the same two-way stud as Granlund is, but Haula won’t break the bank to sign given his injuries. Haula has great wheels and would be able to keep up with McDavid’s speed, and, as I said, he isn’t that far removed from being a 29-goal guy in Vegas.

Some more cheaper options would be, Conor Sheary, a guy who’s made a living playing with Sidney Crosby, or Derek Grant, who had a surprising 15-goal season between Anaheim and Philadelphia this year.

That’s obviously not a very exciting free-agent market, so let’s look at some fits that could come through trade.

The Lightning are in a difficult salary-cap bind with Anthony Cirelli and Mikhail Sergachev in need of new deals. I mentioned Yanni Gourde as a centre the Oilers could pursue, but Ondrej Palat, a great two-way winger, also fits Edmonton’s needs. He’s signed for two more years at $5,300,000.

Speaking of cap issues, there’s also the Toronto Maple Leafs who badly need to free up some cap space to improve their blueline. Either of Kasperi Kapanen or Andreas Johnsson, who have reasonable cap hits at $3,200,000 and $3,400,000 respectively, make sense. I think Kapanen, who boasts amazing wheels and is great on the penalty kill, would be an especially good fit.

There’s also a couple of impending free agents on Edmonton’s roster that we haven’t yet discussed.

Tyler Ennis, who was acquired at the trade deadline, is set to become an unrestricted free agent. He scored 14 goals and 33 points in 61 games in Ottawa and then put up two goals and four points in nine games with the Oilers. Ennis also put up a goal and an assist in the playoffs before unfortunately suffering a broken leg.

There isn’t an overly huge sample size between McDavid and Ennis to draw any conclusions, but he’s a speedy, tenacious, and versatile player who would probably be worth keeping around, even if it wasn’t to play on the top line.

What about Andreas Athanasiou? He was Ken Holland’s big deadline add, as it cost two second-round picks to bring the former Red Wing into the mix.

Athanasiou is a restricted free agent with a pretty expensive qualifying offer. In 2018-19, he scored 30 goals, so there’s obviously a player there, but his 2019-20 season left a lot to be desired. Athanasiou scored just 11 times between Detroit and Edmonton and put up a paltry minus-46 rating in the process.

But, still, Holland paid the price to acquire Athanasiou for a reason. It’s just difficult to say whether he’s the ideal fit to play alongside McDavid. His size and speed are a great complement, but his defensive game leaves a lot to be desired.

James Neal was McDavid’s most common left winger last year. While Neal was money on the power-play, he looks toast at even-strength. Neal and McDavid got outscored 16-to-11 at even strength over 237:54.

A really interesting one actually is Joakim Nygard. The speedy Swede played just 54:43 with McDavid, but the duo was dynamite in that small sample size, outscoring opponents 6-to-2. Nygard has great wheels and plays a smart two-way game. He’s far from your exciting big-name, but he has the tools.

Tyler Benson could warrant a look alongside McDavid. He doesn’t have the wheels you’d like for a McDavid linemate, but Benson plays a very smart game and has a great hockey sense. Also, there’s Jesse Puljujarvi, who may or may not be back in Edmonton next season. Over 407:45 together, McDavid and Puljujarvi have outscored opponents 24-to-15.

There’s a lot to consider here, but, ultimately, what it comes down to is that Connor McDavid needs a quality two-way winger to play with.

Ryan Nugent-Hopkins was that guy in the playoffs, and while they make a very good duo, it comes at the cost of harming the team elsewhere in the lineup. Removing Nugent-Hopkins from the Draisaitl and Yamamoto trio breaks up arguably the most dominant line in the league. Stapling Nugent-Hopkins to McDavid’s left also takes away what might be Edmonton’s best option at creating a strong third line.

Do you pony up for a quality third-line centre and keep Nugent-Hopkins as a winger? Will there be enough room for a third-line centre upgrade and a goalie upgrade? Will you still be able to afford Andreas Athanasiou afterwards? Are the best solutions internal? Could Jesse Puljujarvi make an impact?

It’s difficult to say what the answer is here. Ken Holland has his work cut out for him this fall.