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Even after drafting Connor McDavid, it took the Edmonton Oilers over half a decade to become Stanley Cup contenders legitimately. Yes, the Oilers almost made it to the Western Conference Finals in 2017, but that was sandwiched between missing it…

Cynthia Ryley Delaney argues that two trades between the Edmonton Oilers and New York Islanders under former general manager Peter Chiarelli severely hindered Edmonton's rebuild. On draft day in 2015, the Oilers sent the 16th and 33rd overall picks to New York for defenseman Griffin Reinhart. The Islanders used those assets to draft Mathew Barzal and trade up for Anthony Beauvillier, while Reinhart played only 29 regular season games for Edmonton.
The writer also criticizes the June 2017 deal that sent Jordan Eberle to the Islanders for Ryan Strome. Delaney considers the subsequent handling of Strome, who was later traded to the New York Rangers for Ryan Spooner, an unforced error driven by salary cap mismanagement that cost Edmonton valuable offensive depth during Connor McDavid's early seasons.
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