At the conclusion of the 1980–81 season, the NHL Central Scouting Bureau ranked Benning as the second-best North American draft-eligible prospect behind only Dale Hawerchuk.

[4] His performance in the WHL garnered interest from several National Hockey League scouts, including Johnny Bower of the Toronto Maple Leafs.

[8] Following a difficult season with the Leafs, coach Mike Nykoluk openly questioned whether the lineup's influx of prospects was the correct decision for the roster.

[9] Though Benning's puck-handling skills provided him with security within the team's lineup, critics wanted him to play with greater physicality.

At the midway point of the season, speculation existed that he and teammate Börje Salming would be chosen to represent the Campbell Conference All Stars at the 36th National Hockey League All-Star Game.

[12] The Leafs also considered nominating Benning for the Bill Masterton Memorial Trophy, although they ultimately selected Gary Nylund instead.

[17] Benning expressed uncertainty about the team's interest in retaining him, believing he would play elsewhere, as they had experienced some success while he was injured the previous season.

[17] In addition, the Leafs had recently hired new coach John Brophy, whose physical brand of hockey was believed not to be compatible with Benning's style of play.

[23] Following a streak of nine consecutive games scratched from the Canucks' lineup, the team requested that Benning be demoted to their International Hockey League affiliate Milwaukee Admirals, although he declined.

[24][25] After a brief period of uncertainty with the Canucks in which he was told not to attend practice, Benning was asked to rejoin the team after an injury to Harold Snepsts vacated a roster position.

In his first off-season with the organization, he made several roster moves including the firing of head coach John Tortorella after just one season on the job following by trading of forward Ryan Kesler to the Anaheim Ducks (at Kesler's request) at the 2014 NHL Entry Draft, the signing of goaltender Ryan Miller and the acquisition of several players such as Nick Bonino, Linden Vey, Radim Vrbata, and Derek Dorsett.

At the 2016 NHL Entry Draft, Benning made inappropriate comments about attempting to acquire Montreal Canadiens defenceman P. K. Subban and pending unrestricted free-agent centre Steven Stamkos, who was still under contract with the Tampa Bay Lightning.

[37] On December 5, 2021, Benning was fired as general manager of the Canucks along with head coach Travis Green after a home loss against the Pittsburgh Penguins.