What Can I Do for You Today? Remembering Jim Gregory ’55, OSM

Joe Younder ’56

“What can I do for you today?” or “How can I help you?” If you were with your signicant other, he would quickly say, “has he told you lately... how beautiful you are?” Such words were the lifelong mantra of one James Michael Gregory, so eloquently expressed by his son David on November 2, 2020, at Blessed Trinity Catholic Church, Jim’s and wife Rosalie’s long-time parish.

Jim, a Dunnville, Ontario native, arrived at St. Mike’s in 1953 to enter Grade 12 and take up residence in Tweedsmuir House - boarding along with brothers Les Du ’54, Dick ’55, OSM and Murray Costello ’53, and Billy Dineen ’52.

“Jim was one of the great guys who, all his life, would go out of his way to help you,” relates Dick. Bob Pallante ’59 echoes Lou Angoi’s ’57 comments of “lile Jimmy shooting a good game of pool and regularly beating the likes of Tom Micallef ’55 and Gerry Cheevers ’59”.

Although Jim’s inuential role in hockey was not the focus of David’s eulogy, it is a fact that while playing for the Kerry Blues football team, and running track, Jim tried out twice for the Jr. B club and was cut both times by Fr. Ted Flanagan ’32, CSB. It was here too at St. Mike’s that a young Mr. Dave Bauer ’44 saw some potential in Jim and oered him a job with the Midget team. eir relationship eventually led to Jim being hired by Staord Smythe in 1959 to work in the Leafs’ amateur farm system.

Christmas Day 1971 with nephew Blair and niece Leslie

“I am truly indebted to Fr. Bauer and Staord who put me on the hockey path,” Jim said in a 2007 Blue Banner article. It was a remembered act of kindness that Jim passed on to others throughout his life.

Joe Younder with Jim at the NHL Oces in 2005 St. Michael's College School Majors' trainer, late 50s

As they say, the rest is history: helping Bob Davidson recruit dra prospects, maintaining ties with St. Mike’s that saw them win the Memorial Cup in 1960-61, to, in 1969, at the age of 33, replacing Punch Imlach as the Leafs’ General Manager. Jim was a success and one of the rst NHL managers to recognize Europe as a talent pool for the NHL. For the next decade, the Leafs made the playos eight times. Jim and David, Christmas Day '84

Director of Central Scouting, Senior Vice President of Hockey Operations, inducted into the Hockey Hall of Fame in 2007, and recipient of the Order of St. Michael (OSM) in 2012, Mr. Gregory, as many were inclined to call him, did it all while remaining a man of integrity, loyalty, and generosity.

What about Jim Gregory the father, the husband, the grandfather, the brother, the uncle, the colleague, and the friend?

“My sisters and I would tell you that to have him as our father was a truly great thing. You knew you were loved. He was our dad. He taught us generosity, because he lived it; he taught us respect and caring, because he lived it,” eulogized David.

Jim with daughters Andrea and Maureen and son David, Christmas in Haliburton 1978

ere’s more. Rosalie’s sister, Rita, and her husband, Charlie Pemberton, have 60 years of memories.

“Jim was caring, thoughtful, and generous to the max. He never came for a visit without prizes for autistic kids’ charity auctions or a trunk full of baseball hats, jackets, and NHL memorabilia to be given away,” reminisces Charlie. “Family dinners - his favourite meal being pasta (the thinner the noodle the beer), Haliburton coage gatherings, barbecuing, and being there for others in sickness and in health, were enjoyable constants in Jim’s life. It was a known fact that, when a friend or family member was ill, Jim would oer to get them appointments with the many specialists he knew from hockey.”

L-R, Daughter Maureen, Sister-in-law Rita, Lake Simcoe '80

DEEDS TRULY DO SPEAK en, there’s the story of David’s sons, Kade and Lyle, being taken by their grandpa to a game in Pisburgh. When Jim drove into the parking lot, the aendant had a big smile on his face, and immediately directed Jim to the best parking spot. When he walked into the building, the guys on the arena oor, preparing the ice, thanked him for coming. Happy to see him, they all came up and gave Jim a hug. e amazing thing was he got the same reaction from the CEO, the general manager, the coaches, and everyone in the arena. It didn’t maer who it was. To Jim, everybody was equally important. He was received by all with welcoming hearts and open arms.

Susan Snow, Jim’s Executive Assistant since 1993, writes, “Jim was a mentor and father gure, a dream boss. He possessed those pleasant, kind, and compassionate qualities that fellow colleagues embraced. His Hockey Hall of Fame induction is a testament to his concern for others and contribution to the game he loved. Moreover, he embodied those Catholic teachings of helping the less fortunate by puing smiles on the faces of those who had lost hope. I will miss him.”

L-R Rosalie, Jack Kentish '55, Jim in Costa Rica 2007, and their driver

Tom Larscheid, retired colour commentator for the Vancouver Canucks from 1977-2010, speaks of their 50-plus-year friendship. “When Jim coached the Vancouver Canucks of the Western Hockey League. He oen talked about his experiences at St. Mike's, which really laid the groundwork for his career in hockey. Jim loved every aspect of the game. To mention all of Jim's accomplishments within the hockey world would take forever. His induction into the NHL Hockey Hall of Fame says it all. He always knew how to have fun and enjoy life. I learned so much from him both professionally and personally. He was loved and respected by everyone. Jim was one of a kind and I consider myself very lucky to have had him as my best friend for more than 50 years. I have so many wonderful memories to hold onto thanks to Jim, his wonderful wife, Rosalie, and children, David, Andrea, Valarie, and Maureen. Jim was the best.”

Mike Murphy, Senior VP of NHL Hockey Operations relates, “Jim was a kind, generous man, a role model who cared about people. He oen put friends and family ahead of himself. He loved the game of hockey like very few people love it. Besides supporting his former players if they were in need, he also, in recent years, worked with NHL on-ice ocials who he knew

Jim's and Rosalie's 60th Wedding Anniversary, May 2019

needed personal support. Jimmy never pounded his chest about helping people. It was just his nature. He treasured his family and grandchildren and bragged about their success. When I rst joined NHL Hockey Operations, he held my hand and guided me through the diculties of the hockey business until I had learned enough that I could walk on my own. I miss Jim everyday. God bless him.”

Kimm Bailey, Gina Cramarossa, and Stephanie Nicholls, of the St. Michael’s College School Oce of Advancement write: “We had many dealings with Mr. Gregory over the years. He was a special gentleman, truly a friend to all he met. Jim was very devoted to his family, oen sharing accomplishments of his grandchildren or the plans he and Rosalie, his beloved wife, had for the weekend or an upcoming trip. Jim was a proud alumnus, donor, and supporter and oen could be seen aending events or coming to St. Michael's unannounced to say hello. He was active among his classmates and enjoyed planning and aending the Class of 1955 reunions. He never spoke a bad

Top L-R: Bob Clancy '51, Peter Grossi '54, Jack Dockery '53, Frank Turano '53 Boom L-R: Bob Savage '57, Bob Pallante '59, Tom Micallef '57, Jim Gregory, OSM, Dave Keon '60, OSM, Bob McKnight '57, Cesare Maniago '59, Gene Cuccia '52, OSM word against anyone and put the feelings of others before himself no maer how he was hurting.”

On a personal note, I remember on June 23, 2011 being with family at the Xcel Energy Center in Minnesota where our grandson, Ryan Murphy, was in the rst-round dra. Jim, overseeing the event, waved and walked up the 15 steps to shake our hands. Some things you never forget. No maer where he went, he was greeted with respect and admiration.

ere’s no doubt the Gregorys embraced a loving extended family dynamic. “My mom’s three sisters did not have children, so my aunts and uncles treated us like we were their own kids. Norma and the late Lorne Melara, Rita and Charles Pemberton, and the late Elaine and Joseph Melara were special family to us. In fact, when they all met with Jim’s family in Dunnville, it was like royalty arriving and we were like kings and queens coming to visit,” Dave remembers.

Jim with daughter Valerie, Christmas 2000

It doesn’t take long to see there’s a paern here. When you were around Jim, he made you feel like what you needed was the most important thing he was dealing with. is is something that very few people possess. But he did it his entire life - every day, even though he considered it a life in which he “never worked a day”.

Jim Gregory the man, the husband, the father, the brother, the grandfather, the uncle, the colleague, the hockey guy, the friend - it’s all here.

In the many emails I exchanged with David one stands out, in which he concluded, much like his father: “Just let me know what I can do for you, whatever you want.”