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 significant 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 Duff ’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 Angotti’s ’57 comments of “little Jimmy shooting a good game of pool and regularly beating the likes of Tom Micallef ’55 and Gerry Cheevers ’59”. Although Jim’s influential 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 offered him a job with the Midget team. Their relationship eventually led to Jim being hired by Stafford Smythe in 1959 to work in the Leafs’ amateur farm system.
Joe Younder with Jim at the NHL Offices in 2005 St. Michael's College School Majors' trainer, late 50s
As they say, the rest is history: helping Bob Davidson recruit draft 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 first NHL managers to recognize Europe as a talent pool for the NHL. For the next decade, the Leafs made the Jim and David, Christmas Day '84 playoffs eight times. 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?
Christmas Day 1971 with nephew Blair and niece Leslie
“I am truly indebted to Fr. Bauer and Stafford 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.
“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.
OUR ST. MICHAEL’S COLLEGE SCHOOL COMMUNITY WILL BE STRONGER BECAUSE WE FACED IT TOGETHER
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