[1] However, due to NHL rules, he was required to wait until July 8 to assume his duties in Boston, instead finishing out his time as an assistant general manager with the Senators.

[2][3] Gorton made a number of highly consequential moves that would form the bedrock of Chiarelli's tenure, first trading the Bruins' Calder Memorial Trophy-winning young goaltender Andrew Raycroft to the Toronto Maple Leafs in exchange for Tuuka Rask.

Raycroft would never realize his early potential, while Rask became a Vezina Trophy-winning franchise mainstay for over a decade, and the trade was in retrospect considered a decisive win for the Bruins and one of the worst in Leafs history.

[4][5] Shortly thereafter he signed Zdeno Chára in free agency, who would remain for fourteen years, all of that time as captain, winning the James Norris Memorial Trophy as the league's best defenceman along the way.

[3] In the following years Chiarelli made consequential additions including Johnny Boychuk, Andrew Ference, and Dennis Wideman, the latter later used to acquire Nathan Horton in trade.

Due to the poor performance of the Maple Leafs in subsequent years, both of those were in the top ten, allowing the Bruins to select Tyler Seguin second overall in 2010 and Dougie Hamilton ninth overall in 2011.

[8] Reviewing his tenure at the time of his dismissal, Sports Illustrated opined that he had "built a nice legacy" in Boston, but faulted the later years as "marred by trade disasters, misplaced loyalties and salary cap mismanagement."

However, at the same time, Chiarelli made another decision that would in retrospect be considered one of his worst, trading the sixteenth and thirty-third overall picks to the New York Islanders for defenceman Griffin Reinhart.

[16] In the leadup to the 2016–17 season, Chiarelli made two widely faulted moves, the first being the trade of former first overall draft pick Taylor Hall to the New Jersey Devils in exchange for Adam Larsson.

Hall would go on to win the Hart Memorial Trophy as the league's most valuable player with the Devils, while Larsson had a solid tenure with the Oilers, becoming a fan favourite in the process.

[14][15][17][18] Despite this, the season itself was a success for the team, with the Oilers qualifying for the Stanley Cup playoffs for the first time in ten years and advancing to the second round, narrowly losing to the Anaheim Ducks.

[21][22] The 2017–18 season saw the Oilers regress markedly from their prior results, and they did not qualify for the 2018 Stanley Cup playoffs despite McDavid leading the league in scoring for the second consecutive year.

[25][15] While team executive Bob Nicholson would subsequently claim that the contract extension for Koskinen had been a group decision of management, many in the media speculated that its proximity to Chiarelli's firing were indicative of a causal connection.