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When the 2022-23 National Hockey League season ended, Gregor figured he had done enough with the San Jose Sharks to ensure that he would be qualified by the club. In 57 games, Gregor scored 10 goals and had seven assists, providing some enthusiasm from the fourth line. Despite thinking his exit interviews with the Sharks were positive, the six-foot, 188-pound Gregor did not receive a qualifying offer from San Jose general manager Mike Grier, making him a free agent.
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