But Carlyle denied having signed with the Cincinnati Stingers, and Gregory got his signature on a Leaf offer right away. Then, the Stingers entered the fray, saying Carlyle had signed and they were taking him to court for breach of contract. All was eventually sorted out, and the Leafs were winners at the Stingers expense. Except that after just two years, Toronto gave up on him. They traded him to Pittsburgh with George Ferguson for Dave Burrows, and Carlyle's career took off.

Two years later, in 1981, he won the Norris Trophy, something no Leaf had even won. Six seasons in Penguins colours and he was off to Winnipeg for the last nine years of his career. Along the way, he was cut from the 1981 Team Canada for the Canada Cup by coach Scotty Bowman after showing up overweight.

In 1989, his one international experience, he was humiliated by the IIHF at the World Championships in Stockholm. Chosen to provide a urine sample after Canada's game with West Germany, he apparently failed the test and withdrew so as not to taint future results of the team. In the wake of the Ben Johnson scandal, Carlyle's case was front-page news across Europe, another Canadian cheat. His name was mud. A day later, the IIHF announced that the B sample was clear as mountain air. No explanations or apologies only a shame-faced hockey player that had done nothing wrong.

After retiring, Carlyle stayed in the Jets organization as a colour commentator for the radio and a staff member of the team's public relations department. He then became an assistant coach and when the Jets moved to Phoenix and the Manitoba Moose of the IHL moved in, Carlyle remained as first an assistant and then a head coach. In 2000, he became the team's general manager. His last NHL goal was scored against the team that had given up on him too soon, Toronto.