I was emcee at a charity event honouring Jim Gregory about 15 years ago. I kiddingly talked about how I was angry at Jim Gregory. This of course caught the crowd by surprise, knowing how highly I respected him and what a strong personal relationship we always had. I went on to explain that, as my first boss in a hockey organization, he did things like treat me with respect, champion me and nurture me as a young executive. He always had my back and always made me feel valued both personally and professionally.
He did that with everyone in our (at the time) small Maple Leafs executive office.
I further explained that my bone of contention was that, since he was my first boss, I thought that was the way it would always be in the real working world. I kidded that he ill-prepared me for a world that I soon learned had only one Jim Gregory. I could see a modest, but proud, smile from Jim sitting at the head table and an audience that nodded in agreement.
He was usually the smartest man in the room, but never flaunted it. A true “big shot” in every manner, but never acted that way in the slightest.
His professional legacy as general manager of the Toronto Maple Leafs is never really given its appropriate appreciation. He took over a team in tatters and twice accomplished quick and successful rebuilds. The last of Toronto’s four Stanley Cups in seven years came two years prior to when Jim was hired as Leafs GM in 1969. Those two years may as well have been 10. Losing players to retirement, NHL expansion, bad trades and the selling of top prospects left the cupboard bare.
By drafting the likes of Darryl Sittler and bringing other young players into the Leafs lineup, Jim made significant strides in three years. He made the Leafs respectable again.
Then, in 1972, the rival World Hockey Association started. Leaf owner Harold Ballard was in the minority by not believing in the legitimacy of the upstart rival league and refused to allow Jim to get into bidding wars with WHA teams that were negotiating with Leaf players, so the strides Jim had made in three years were quickly halted. Lost to the WHA were elite goaltender Bernie Parent as well as valuable centre Jim Harrison. Young defencemen like Jim Dorey, Brad Selwood and Rick Ley also left, along with veterans Paul Henderson and Leaf icon Dave Keon.
What could have been a disaster, Jim made a mere on-ice hiccup. He got right back to work and drafted the likes of Lanny McDonald, Ian Turnbull, Tiger Williams, Mike Palmateer and scored a major coup by being a pioneer in the Swedish hockey market, signing Borje Salming and Inge Hammarstrom. Jim was also able to retain players like Sittler and McDonald for less money than the WHA offered because they believed in what he was doing in Toronto. The mid-1970s Leafs team with Red Kelly as their coach were soon an exciting young squad with character that sat just below elite teams Montreal, Boston and Philadelphia in the NHL standings.
Jim also proved to be an innovator in hiring Roger Neilson (in 1977) — his last coaching hire as Leafs GM. Though Jim could be old school in many ways, he also saw and appreciated what was new and could have a positive impact on his team. Neilson is the pioneer of all that is a big part of the game today. Video, statistics, analytics — You name it Roger did it. Jim Gregory saw it, appreciated it and helped introduce it to the NHL.
Jim had actually been hired by Stafford Smythe as Leafs GM and always felt that Smythe was not given his just due as a great hockey man. Jim was loyal to a man who gave him a big break. When Smythe died suddenly just two years later, Harold Ballard took over as Leafs President and that made for a bumpier ride in the GM’s chair. Jim wasn’t Ballard’s hire.
I was working part-time in the Leaf offices at that time and marvelled at how Jim dealt with his very difficult and not-so-supportive boss. He continued to improve his hockey team and build a front office that worked hard and appreciated being valued.
Among the criticisms directed at Ballard was his lack of appreciation for the great Leafs Alumni. It was Jim who worked around that to a degree by finding scouting jobs for both Leafs greats George Armstrong and Johnny Bower right after they retired. An example of how Jim worked without fanfare, but got results.
Jim was relaxing on a float in the water at his cottage in early July, 1979. He was getting set for another season as Leafs general manager after having a successful one with Neilson as coach that ended in a disappointing second-round playoff loss to the eventual Stanley Cup champion Montreal Canadiens. Jim’s wife, Rosalie, let him know that NHL Vice-President Brian O’Neill was on the phone. Though perplexed why O’Neill would be calling him at his cottage, Jim quickly went up to the cottage to take the call.
O’Neill wanted to offer Jim a job as Director of the NHL’s Central Scouting Bureau. Jim was baffled. He told O’Neill that he still preferred being Leafs GM. And O’Neill was surprised by Jim’s answer. He shared that he had talked to Ballard the day before and was told Jim had been fired as GM. That’s how Jim found out his days with the Toronto Maple Leafs were over and pretty well summarized the difficult waters he had navigated.
That is why I have continued to say and believe that Jim Gregory is the most underrated Leafs executive ever.
The Leafs’ loss (and it was a significant one) was the NHL’s gain. Being so well-liked and respected, Jim quickly rose through the ranks in the NHL offices to oversee officiating, hockey operations and the Hockey Hall of Fame selection committee. Even Bob Goodenow, when NHL–NHLPA relations were at their most contentious, valued Jim’s friendship and expertise even though he was on the “other side.” Jim just had that way. You could not dislike him. You understood that he always acted in the best interests of the game and the people involved in it.
When Gary Bettman was hired as NHL Commissioner in 1993 the thinking was that he might shut down or diminish the NHL league offices in Toronto and move everything to New York and that he also might make significant personnel changes in hockey operations. But Bettman, too, quickly appreciated what Jim was all about. This gave Bettman early credibility inside the NHL world.
The Toronto offices remained and grew, as did Jim’s stature in the game as he was promoted to a Vice-President and assumed a myriad of responsibilities. The Commissioner soon decided that as he looked to grow the NHL, it was going to grow with Jim Gregory playing a big part in it.
When my brother Bob and I visited Jim two weeks ago, it was just like our great memories of chatting in an office, at a hockey game, in a car, whatever. Despite his frailness Jim remained his positive and upbeat self. He and Rosalie couldn’t say enough good things about how well “Mr. Bettman” had treated them. Whatever one might think of the Commissioner, this will always be a positive legacy.
Others like Sittler, McDonald, Williams and Salming had also come by to visit him the last few weeks. I still thought I might get in another visit or two.
I have spent more time smiling thinking of Jim Gregory since hearing the news of his passing. I think of my own story as one who owes a big personal debt to Jim for how he helped my career, like hundreds of others.
But mostly, I think of that great big laugh he would give after he would tell one of his many jokes…no matter how funny it was.