Kelly was appointed as executive director of the NHLPA, replacing Ted Saskin who had been ousted for secretly monitoring player e-mail accounts.
[3] On August 31, 2009, Kelly was unexpectedly fired as head of the National Hockey league Players' Association following several hours of meetings in Chicago.
Russ Conway, the former Lawrence Eagle Tribune NHL and Boston Bruins sportswriter who had helped to expose Alan Eagleson's corrupt practices, described Kelly as the first "true, clean" leader the NHLPA ever had, and said "this is a very sad day for hockey.
Kelly was not involved with the NHLPA when the deal was negotiated; nonetheless he stated publicly that he did not want to see another work stoppage when the agreement expired on September 15, 2011.
[7] Kelly has been a practicing trial lawyer for over 30 years, with extensive experience in white collar criminal defense, internal investigations, complex civil litigation and crisis management.