[3] After leaving the public sector, he joined a law firm, and then was hired by the Philadelphia Flyers where he served as chief operating officer and executive vice president.
[3] He served as the National Hockey League's (NHL) general counsel and vice president under John Ziegler, Jr., and held that role for 15 years.
The announcement of the Panthers attracted the ire of Phil Esposito, president and general manager of the young Tampa Bay Lightning (who began play one year before Florida in 1992), as Stein initially told Esposito that no teams would be added until 1996, as the Lightning were supposed to have time to develop a fanbase in the state of Florida.
[10][9] Stein served as NHL president for a year until shortly after the owners appointed Gary Bettman to the newly created post of commissioner.
[12] Stein was behind the Hall of Fame board while president, spearheading a change in the voting process by simple majority with no secret ballots.