Even with Connor McDavid in the fold, it took the Edmonton Oilers more than five years to turn into true Stanley Cup contenders. They came close in 2017, missing the Western Conference Final by a step, but that run sat between a missed playoff berth in 2016 and back-to-back misses in 2018 and 2019. When the Oilers finally got back in, the 2020 and 2021 postseasons ended quickly - first-round exits, one win total.
A big chunk of that wasted stretch traces back to Peter Chiarelli’s tenure as general manager. And if you want the clearest examples of how the rebuild got knocked off track, look straight at the two trades he made with the New York Islanders in a two-year span: Griffin Reinhart and Jordan Eberle.
The Reinhart deal is still the one that stings the most.
On June 26, 2015, the same night Edmonton drafted McDavid first overall, the Oilers shipped out the 16th and 33rd picks in the NHL Draft for Reinhart. At the time, Reinhart had already faded as a prospect despite being selected fourth overall in 2012. He had only eight NHL games and 59 AHL games on his resume, though he did bring a strong junior pedigree with two Ed Chynoweth Cups and a Memorial Cup with the WHL’s Edmonton Oil Kings.
The trade was mocked immediately, and the years since have only made it look worse. The 2015 draft turned into one of the deepest in league history, and the Islanders cashed in right away with the 16th pick by selecting Mathew Barzal. Barzal has since put up 153 goals and 534 points in 611 NHL games, plus 17 goals and 45 points in 60 playoff appearances.
And he wasn’t even the best name still on the board. Kyle Connor went 17th, Thomas Chabot 18th, Joel Eriksson Ek 20th, Brock Boeser 23rd, and Travis Konecny 24th.
The Islanders also used the 33rd pick, plus a third-rounder that became Anthony Cirelli, to move up to 28th and take Anthony Beauvillier. Sebastian Aho went 35th, two spots after Edmonton’s original pick, and he’s since become a Stanley Cup champion with 318 goals and 730 points in 771 games.
Reinhart, meanwhile, barely lasted in Edmonton. He played 29 regular-season games for the Oilers in 2015-16 and one playoff game in 2017. Across his NHL career, he ended up with 37 regular-season games and two playoff appearances before retiring in 2021-22 after a season in England.
The Eberle trade followed a different path, but it fit the same pattern of damage.
After the Oilers’ 2017 playoff run, Chiarelli sent Eberle to the Islanders on June 22, 2017 for Ryan Strome. There was cap pressure coming, with Leon Draisaitl’s eight-year extension set to begin in 2017-18 and McDavid’s eight-year extension looming for 2018-19. Even so, Edmonton had room to carry Eberle that season, which makes the move look like an unforced mistake.
Strome was coming off a 17-goal, 50-point sophomore season and needed a fresh start. On paper, the swap was a second-line right winger for a right-shot third-line center. The problem was less the trade itself than the chain of decisions around it, from earlier roster missteps to the messy follow-up moves.
Strome’s only full season in Edmonton was respectable: 13 goals and 34 points. But Eberle responded quickly in New York with 25 goals and 59 points in his first season with the Islanders.
Then came the next turn. After 18 games in 2018-19, the Oilers dealt Strome back to the Islanders for Ryan Spooner.
That one hurt right away. Spooner managed only two goals and three points in 25 games with Edmonton after producing 13 goals and 49 points in 80 games for Boston in 2015-16.
Strome moved on and scored 18 goals and 33 points in 63 games with the Rangers, then delivered double-digit goals and 40-plus points in seven seasons.
That whole sequence looked like Chiarelli trying to patch holes and save himself rather than actually improve the roster. After that deal, along with the Alex Petrovic trade that cost a second-round pick and Mikko Koskinen’s extension, Chiarelli was out. He never should have been hired.
Spooner was later flipped for Sam Gagner before the 2019 trade deadline, and that at least worked out for Edmonton. But by then the damage from the Eberle branch of the tree had already been done: a top-six winger out, a third-line right-shot center out, and not nearly enough coming back. Ironically, that’s the exact kind of winger and center this Oilers team could use right now.
In Other News...
Oilers Turn To Matt Tomkins In A Spot Fans Did Not Expect
The Oilers are turning to Matt Tomkins in a spot few would have circled on the calendar, with coach Mike Babcock saying the goaltender will make his Edmonton debut against the New York Rangers. Tomkins was brought up from AHL Bakersfield under emergency conditions after Devon Levi was placed on injured reserve, giving the organization an unexpected look at a depth option it had only recently added on a two-year, two-way deal.
Tomkins does bring prior NHL experience, but this is still a notable moment for a goalie who has spent much of his recent work in the minors and now gets thrown into a high-profile setting right away. For Edmonton, it is another reminder of how quickly the crease can change, and for Tomkins it is a chance to show he can handle a call that arrived far sooner than anyone around the team likely planned. [Read more 🡒]
Oilers Stay Perfect On The Road In Another McDavid-Led Statement Win
The Oilers kept rolling away from home with a 3-1 win over the Rangers, a result that pushed them to 11-2-2 on the season and kept their road mark spotless at 7-0. Connor McDavid set the tone early with a goal and stretched his point streak to 15 games, while Evan Bouchard and Colton Dach added the kind of secondary scoring that has helped Edmonton keep finding answers even when the game tightens up.
There was also a notable subplot in net, where Matt Tomkins made his first start for Edmonton and handled the moment well, turning aside 28 of 29 shots. For a team already carrying momentum through the opening stretch, getting that kind of stability from an unfamiliar name only deepens the sense that the Oilers are building something sturdy as the schedule starts to test them more often. [Read more 🡒]
McDavids October Run Has Oilers Fans Eyeing Hockey History
Connor McDavids October has already pushed his name into a familiar conversation in Edmonton, the kind reserved for the sports rarest scorers and playmakers. He piled up 27 assists in the month, setting the NHL mark for assists in October while also establishing new Oilers franchise records for points and assists over the same stretch, a start that has naturally invited comparisons to the biggest early-season bursts in league history.
The company he is keeping is the point here, because the list now includes names like Wayne Gretzky and Mario Lemieux, with McDavids opening month landing among the most eye-catching runs the NHL has ever seen. For Oilers fans, the intrigue is not just what he has already done but how long this kind of pace can hold, and whether October will end up looking less like a hot streak and more like the beginning of something historic. [Read more 🡒]