March 3, 2024 by Ryan Lotsberg

This is part two of a series about players that the Edmonton Oilers might have to move prior to the trade deadline because you have to give in order to get. Yesterday I wrote about Warren Foegele. Today I’m writing about Dylan Holloway.

Related: To Trade or Not to Trade: Warren Foegele

Elliotte Friedman said that the Oilers are trying to add two forwards and one defenceman during his Saturday Headlines segment on Hockey Night in Canada on Saturday night. The Oilers are looking at adding a top six winger and potentially a depth scoring forward. We also know that the Oilers were interested in Chris Tanev, so they have eyes on improving the right side of the defence as well.

If you want impactful players at the trade deadline, then you have to be willing to part with first round picks, whether they be future or past first round picks. Oilers GM Ken Holland traded a first rounder and a former first round pick (Reid Schaefer) along with Tyson Barrie to the Nashville Predators for Mattias Ekholm last season. It will certainly cost at least a first round pick (or a former first round pick) to land players like Jake Guentzel, Pavel Buchnevich, or Sean Walker.

Friedman also said that the Pittsburgh Penguins prefer prospects over draft picks in a return for Guentzel. The Penguins want to remain competitive in the waning years of the Sidney Crosby, Evgeni Malkin, and Kris Letang era. They brought Erik Karlsson in this season so they can take a few more runs at a Stanley Cup. I’m sure they don’t want to trade Guentzel, but he has turned down their extension offers to date. It makes sense that they want players that are closer to being able to contribute in the NHL in exchange for Guentzel.

The Vegas Golden Knights seem to be the favourite to land Guentzel due to the fact that they have the cap space to add him without Pittsburgh having to retain any salary because of Mark Stone’s injury. However, the Golden Knights have more picks than prospects. The Oilers have more prospects available than they have picks. That increases the Oilers’ odds of landing Guentzel.

That brings me back to Holloway. The 2020 fourteenth overall pick is the type of player that the Penguins would be looking for in exchange for Guentzel. A former first round pick with middle-six potential that is ready to contribute at the NHL level. Holloway is a burner that has shown a willingness to be physical. He can play wing or centre, and he has shown his soft hands on occasion. 

Holloway has 36 points in 49 career AHL games, and thirteen points in 81 NHL games. He’s shown quite well in the AHL, but he basically has a full NHL season under his belt and has minimal production to show for it. While it’s true that he has been frustratingly sheltered in the NHL, it’s also true that he has failed to do much with the few opportunities that he has been given higher in the lineup.

One of the first things that CEO Jeff Jackson did after he was hired last summer was firing Head of Amateur Scouting Tyler Wright. The cold, hard reality is that no picks made during the Wright and Holland era have become impactful parts of the Oilers roster. Kaiden Guhle, Lukas Reichel, Dawson Mercer, and Braden Schneider were all taken within the five picks immediately after Holloway was selected in the 2020 draft. All four of those players have already had more NHL success than Holloway has. 

We can keep going down the list with Yegor Chinakov, Hendrix Lapierre, Tyson Foerster, Connor Zary, Justin Barron, Jake Neighbours, and Ridly Grieg all having gotten off to better starts to their NHL careers than Holloway. That’s eleven of the next fourteen players drafted immediately after Holloway. I’m not saying Holloway can’t get there, but Holloway’s slow start in comparison to the players I’ve listed here is a stain on Wright’s resume. My point here is that I don’t think the Oilers are married to any of their prospects, including Holloway.

I like Holloway as a player, and I’m sure that his production will improve. Taking him off the Oilers roster would make the team slower, which is a problem for a team with limited speed aside from the superstars on the roster. However, you have to weigh that against the potential return for the Oilers. An impactful top six winger like Guentzel would warrant sacrificing Holloway in my opinion.

I like that idea less if Guentzel was to be a rental though. Guentzel’s current cap hit is $5.8 million, and he’s going to command a significant raise this summer. Guentzel recently rejected a six-year contract extension with an AAV of $8.5 million offered by the Penguins. That gives us a sense of what Guentzel will be seeking in his next contract. The Oilers would have to move Jack Campbell’s contract and make sacrifices in other areas of the roster to be able to re-sign Guentzel next season. Potential sacrifices could include Evander Kane or Brett Kulak.

Trading Holloway isn’t a must for the Oilers, but I do think that the Penguins would ask for him in any trade involving Guentzel. We know the Oilers will be competing with the Golden Knights for Guentzel. The Athletic recently ranked the Oilers’ prospect pool 25th in the league. The Golden Knights’ prospect pool was ranked 23rd in the league. 

The Golden Knights have Brendan Brisson, the 29th pick in the 2020 draft, to offer. Brisson has six points in twelve NHL  games this season. Brisson is the son of Sidney Crosby’s agent Pat Brisson. That connection along with the Golden Knights being able to absorb Guentzel’s full cap hit and their having more draft capital to offer could all put the odds in the Golden Knights’ favour here. Brisson and 2023 first rounder David Edstrom are the only former first round picks in the Golden Knight’s system right now though. The Oilers have Xavier Bourgault and Philip Broberg as well as Holloway.

The other thing the Oilers could do with Holloway prior to the trade deadline would be to send him down to the Bakersfield Condors. That would open up $925,000 in cap space and a roster spot for a forward. Holloway is the only player on the Oilers current active roster that is exempt from waivers, so he could easily be sent down. Holloway could be recalled for the playoffs when the salary cap is no longer an issue.

Related: Oilers 2024 Trade Deadline Preview