Holloway Is Latest in Long Line of Draft Picks That Don’t Stick With Oilers

In 2014 and 2015, the Edmonton Oilers used their top draft pick to select, respectively, Leon Draisaitl (third overall) and Connor McDavid (first overall).

As part of the Oilers, Draisaitl and McDavid have combined to rack up 1,832 regular season points, win the Art Ross Trophy six times, the Ted Lindsay Award five times, and the Hart Trophy four times. In June they helped Edmonton reach the Stanley Cup Final for the first time in 18 years.

McDavid is presently the best player on the planet, and Draisaitl is somewhere in the top 5 to 10. They’ll both go into the Hall of Fame as soon as they’re eligible. Arguably no team has drafted two better forwards in the first round in consecutive years, and that includes the Pittsburgh Penguins taking Evgeni Malkin second overall in 2004 followed by Sidney Crosby at No. 1 in 2005.

But since then, Edmonton’s ability to draft and develop forwards has been an abject failure. The centres and wingers drafted by the Oilers in the last nine years fell into one of three categories: they haven’t reached the NHL; they had a disappointing tenure in Edmonton before the Oilers gave up on them; or they were traded away without even playing a game for the Oilers.

And now there’s a fourth category: they left as a restricted free agent by signing an offer sheet that went unmatched.

Oilers Don’t Match Holloway’s Offer Sheet

On Aug. 20, Dylan Holloway signed a two-year contract with the St. Louis Blues after the Oilers declined to match the offer sheet that he had signed a week earlier.

Edmonton’s first-round pick (14th overall) in the 2020 NHL Draft, Holloway had nine goals and nine assists in 89 career regular-season games with the Oilers. The 22-year-old suited up for every playoff game during Edmonton’s run to Game 7 of the 2024 Stanley Cup Final, and was projected to be part of the Oilers’ bottom six in 2024-25.

Dylan Holloway Edmonton Oilers
Dylan Holloway, Edmonton Oilers (Photo by Andy Devlin/NHLI via Getty Images)

Holloway’s departure means that of all the forwards Edmonton has drafted since McDavid in 2015, it’s quite likely none will be uniform when the Oilers open the coming season against the Winnipeg Jets on Oct. 9.

In fact, Raphael Lavoie (38th overall pick in 2019) is the only forward that Edmonton has drafted in the first four rounds since 2016 that is still part of the Oilers’ organization. Lavoie, who made his NHL regular season debut playing seven games in 2023-24, recently re-signed with Edmonton on a one-year, two-way deal, and seems likely to spend most of the coming season in the American Hockey League (AHL).

Forwards Had Failed Stints With Oilers

From 2016 to 2018, the Oilers drafted four forwards in the first two rounds. All of them went on to play for Edmonton, but none had the impact that was hoped for when the Oilers selected them in their respective drafts:

Jesse Puljujarvi (fourth-overall pick in 2016) suited up for 317 regular-season games over parts of six seasons with the Oilers. After having a difficult time during his first NHL stint, the winger went back home to Finland for the 2019-20 season, before returning to the Oilers in 2020-21. His second go-around in Edmonton went much better, but he still never scored more than 15 times in a season, and was ultimately traded to the Carolina Hurricanes in 2023 for the rights to prospect Patrik Puistola, a Finnish forward. Puistola never signed with the Oilers.

Tyler Benson (32nd overall pick in 2016) only appeared in 38 games with the Oilers. The left winger never seemed to be able to get on track, suffering several injury setbacks dating back to his junior career in the Western Hockey League (WHL), and struggled offensively at the NHL level, scoring just once. Edmonton elected not to re-sign Benson after the 2022-23 season, and he spent 2023-24 playing with the Henderson Silver Knights on an AHL contract.

Kailer Yamamoto (22nd overall pick in 2017) spent parts of six seasons with the Oilers, playing 244 regular season games and 34 in the playoffs. The winger appeared to have a breakthrough campaign in 2021-22, when at age 23 he recorded 20 goals and 21 assists in 81 games, but took a step back in 2022-23, scoring just 10 times. On June 29, 2023, in what was essentially a salary dump, the Oilers dealt forwards Klim Kostin and Yamamoto to the Detroit Red Wings for future considerations.

Ryan McLeod (40th overall pick in 2018) was a fixture in Edmonton’s bottom six over the last three seasons, playing centre and wing. Last season was his best offensively, with 12 goals and 18 assists, and he scored four times in the 2024 Playoffs. On July 5, in a move that allowed the Oilers to shed some salary, they traded McLeod and another one of their drafted forwards, right wing Tyler Tullio (126th overall pick in 2020) to the Buffalo Sabres for forward Matthew Savoie.

Recent Draft Picks Traded Away by Oilers

Outside of the aforementioned four skaters, Holloway and Lavoie are the only forwards drafted by the Oilers going back to 2016 that have played in the NHL. The recent trend in Oil Country has been for Edmonton to trade away its forward prospects before they even get to the NHL.

Xavier Bourgault (22nd overall pick in 2021) spent his first two pro seasons exclusively in the AHL, where he struggled to produce with the Bakersfield Condors, totalling just 20 points in 55 games in 2023-24. On July 15, Edmonton dealt Bourgault and fellow Oilers-drafted forward Jake Chiasson (116th overall pick in 2021) to the Ottawa Senators for forward Roby Jarventie and a fourth-round pick in the 2025 Draft.

Reid Schaefer (32nd overall pick in 2022) didn’t even make it to the pros before Edmonton traded him. On Feb. 28, 2023, eight months after the Oilers drafted the left winger, Schaefer was included as part of a trade with the Nashville Predators that brought defenceman Mattias Ekholm to Edmonton.

Oilers’ Core Is Largely Built Via Free Agency

There have been forwards that Edmonton drafted and ultimately bid farewell to without receiving any compensation, most notably Carter Savoie (100th overall pick in 2020). The left winger, who spent the last two seasons with Bakersfield in the AHL, became an unrestricted free agent this offseason when the Oilers did not tender him a qualifying offer.

So where have all the Oilers forwards come from? According to Elite Prospects, of the 13 forwards currently on the Oilers roster, only three (Draisaitl, McDavid and 2011 No. 1 overall pick Ryan Nugent-Hopkins) are Oilers’ draft picks, while two (Adam Henrique and Vasily Podkolzin) have been acquired via trade and eight (Viktor Arvidsson, Connor Brown, Zach Hyman, Mattias Janmark, Evander Kane, Corey Perry, Derek Ryan, Jeff Skinner) joined the Oilers as free agents.

Related: Hyman Labeled One of Great Free-Agent Signings in Past Decade

To the Oilers’ credit, they’ve done a very good job adding forwards externally: Hyman, signed in 2021 for seven years at a $5.5 million annual average value (AAV), looks like one of the all-time great free-agent acquisitions; Kane and Perry were controversial reclamation projects that proved successful enough for Edmonton to re-sign both after their original Oilers contracts expired; Arvidsson and Skinner signed this offseason for less than might have got elsewhere.

This formula of building from the outside has worked for the Oilers, who came just one win short of hoisting the Stanley Cup in June, but it isn’t sustainable over the long term. The 1980s Oilers were one of the great dynasties in sports history, but years of terrible drafting left them without anyone to step up in the early 1990s once the team’s championship core had moved on. Drafting and developing forwards will be crucial for Edmonton in the years to come.

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