Breaking: Canadiens closing in on deal to sign 22 year old Oilers left wing

As the 2023-24 NHL season comes to a conclusion as the Florida Panthers and Edmonton Oilers continue to compete for hockey’s biggest prize, supporters of already-eliminated teams are likely tuning in, envious of what could have been for their chosen team. Furthermore, the Stanley Cup Playoffs always appear to be the moment where certain players emerge as stars, or perhaps use the high-stakes stage as a springboard for their long-awaited breakthrough.

Dylan Holloway, the Oilers’ 2020 14th overall pick, has finally emerged as a solid middle-six forward with an even greater ceiling after spending the better part of two seasons on the fourth line with less-than-ideal teammates. The former Wisconsin Badger is coming off one of the best games of his young career, scoring two goals and adding an assist in the Oilers’ 8-1 victory against the Panthers, forcing a Game 5. Holloway has found synergy with Leon Draisaitl after being given the opportunity to play higher in the lineup. He has five goals and seven points in 22 postseason games after scoring only nine goals in 89 regular season games.

Despite his rise and the improved quality of his linemates, he still averages less than 12 minutes of ice time each game. He played only 5:24 in the Oilers’ Game 3 loss, his lowest total of the playoffs. He is known for his blistering pace (as evidenced by his spectacular first goal in Game 4), and despite the limited opportunities, he has demonstrated that he is capable of playing with higher-quality attackers.

As the Montreal Canadiens have demonstrated by purchasing two young forwards who are failing to find appropriate opportunities, general manager Kent Hughes and company appear to be interested in buying low on these types of players with high potential. Kirby Dach and Alex Newhook had perhaps underperformed their prior clubs in terms of offensive output, but went on to set career highs in their debut season with Montreal.

Holloway has followed a similar track, but has suffered far more and had virtually no opportunity to showcase his abilities until this tournament. His average ice time increased from 9:35 in 2022-23 to 11:22 this past regular season. The 22-year-old sustained an extended wrist injury following his second season in college and has missed three months of action this season due to a lower-body issue.

With Hughes fully healthy and establishing his value on a Cup-contending group, the time to purchase low may be running out for him and his teammates. He has yet to really break out, but he appears to be going in that direction, and his lack of opportunities thus far implies that the price to get him may not be prohibitively expensive — assuming the Oilers are ready to listen to offers on him.

Holloway spent both seasons at the University of Wisconsin, with Habs star Cole Caufield. Caufield earned the Hobey Baker Award as collegiate hockey’s MVP in 2020-21, while Holloway also had a solid season. While Caufield clearly scored the majority of the goals (30 in 31 games), Holloway managed 24 assists and 35 points in only 23 games, ranking third in the country behind Caufield and Quinnipiac’s Odeen Tufto.

It’s no secret that the Canadiens’ goal is to address their need for a top-six forward, with trade options including Martin Necas, Trevor Zegras, Patrik Laine, and Nikolaj Ehlers. However, Holloway would cost a fraction of the price of any of those players, and while it is unclear whether he can realize his potential as a top-six NHL forward, his string of excellent postseason performances is beginning to persuade critics. He has overcome a nearly season-long injury that required two separate operations after failing to fully heal from the first, and he is demonstrating why the Oilers selected him in the mid-first round.

While there are plenty of choices to fill out the top of the Habs’ front line, Holloway would be an excellent low-cost, undervalued addition. He would not cost as much as a first-round pick plus a highly regarded prospect, like the aforementioned trade options would — possibly more in the range of a similar reclamation project-type player plus a draft pick or B-level prospect. He may not be able to play as a top-six forward right away, but the necessity is not pressing while the team’s rebuilding process continues.While it is very possible that the Oilers desire to keep him after a great postseason performance, his emergence might demonstrate to Canadiens supporters what a hypothetical Holloway-Caufield connection might look like if this wishful thinking comes true.