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Gregory's love of game, Maple Leafs captured in one-of-a kind photo album

Historic images tell story of late NHL executive, former Toronto GM's amazing career

by Dave Stubbs @Dave_Stubbs / Columnist

TORONTO -- Jim Gregory's office at 50 Bay St. in Toronto was steeped in history, decision-making, memories and tradition. It was an influential place of NHL business with a welcoming chair on the visitor's side of the desk, a busy suite stocked with the modern and the vintage -- books and media guides, photos and boxes, sticks and jerseys, business cards, sticky-note reminders, a receipt, a wrapped candy or two on the desk.

Any time I sat across from Mr. Gregory here, I'd be sure to have a full mug of coffee. His storytelling was legendary, some of the greatest moments in League history spun with folksy charm.

(A journalist since 1976, I have referred to three icons in hockey as "Mr." in conversation with them: Jean Beliveau, Gordie Howe and Jim Gregory. Mr. Gregory's gentle protests to me fell on deaf ears.)


Jim Gregory early in his hockey career with the St. Michael's Majors, later as GM of the Toronto Maple Leafs.

It was in that office on Jan. 3, 2018, before and after a memorial service for his dear departed friend Johnny Bower at what was then called Air Canada Centre, that I first noticed the album on a shelf over Mr. Gregory's desk. On the leather-bound book's cover was a photo of then-Toronto Maple Leafs general manager Gregory shaking hands with newly named captain Dave Keon. The photo was taken in Toronto's Maple Leaf Gardens dressing room 50 years ago on Thursday.

Mr. Gregory lifted the album from its stand and slid it across his desk to me. Even with a page-flipping glance, the history it contained took my breath away.

In the days before and since Mr. Gregory's death on Wednesday at the age of 83, I've had time to study the album's 66 pages and 83 black-and-white and color photographs.

The first image is of Mr. Gregory in a team portrait from the 1970s, wearing a Maple Leafs windbreaker; the last is of him beside Maple Leafs icon King Clancy in then-owner Harold Ballard's legendary "Bunker" at one end of Maple Leaf Gardens. The only words in the book appear beneath the latter photo: "ALWAYS A MAPLE LEAF".

Jim Gregory works the phone during his days as Maple Leafs general manager.


The album had been presented to Mr. Gregory by the Maple Leafs about eight years ago, produced by Mike Ferriman, today their director of event presentation and alumni relations. Ferriman poured photos from team files and various sources, including stills that he extracted from videos, into a now-defunct company's online site that would assemble them in an album measuring 15 by 11 inches.

Mr. Gregory was presented the album during a game-night celebration of his career that was held in the Air Canada Centre's Directors Lounge, attended by the guest of honor's family, NHL Commissioner Gary Bettman, Deputy Commissioner Bill Daly and others.

"It's not a complete look at Mr. Gregory's life, but I know that he liked it a lot," Ferriman said.

Jim Gregory with a framed tribute to his hockey life.


There would be no need for even a single photo caption, since the book was a non-commercial souvenir for Mr. Gregory and he would know every face in it.

The earliest image appears to be from the mid-1950s, Mr. Gregory wearing a St. Michael's Majors windbreaker with a shamrock crest on the left side. On the facing page is a St. Mike's major-junior team, in uniform minus skates, standing the length of a Trailways of Canada charter bus. Deeper, a photo of Mr. Gregory being carried off the ice by one of his two 1960s Memorial Cup-winning Toronto Marlboros teams.

There are many Hockey Hall of Fame images from ring presentation ceremonies in the Great Hall, Mr. Gregory having served with distinction as the selection committee chairman from 1998-2014. Included are shots with Bill Hay and Pat Quinn, former chairmen of the shrine, various presentations to referees, Mr. Gregory on stage at several NHL Drafts.

Jim Gregory with Borje Salming, the Sweden-born defenseman he signed in 1973 to play for the Maple Leafs.


There's a beaming portrait of him with Borje Salming and another with Brendan Shanahan, the latter wearing an NHL Research and Development Camp jacket.
Ferriman included four Maple Leafs team photos from Mr. Gregory's 1970s tenure as general manager, and one of himself, albeit in the guise of team mascot Carlton the Bear taken at the 2008 NHL All-Star Game in Atlanta.

I can still see Mr. Gregory playfully sliding his album across his desk to me nearly two years ago, still hear him chuckling as I babbled, flipping through the pages.

During that visit, I would lob a hockey fact to him; where I offered a nugget, he would reply with a heavy gold ingot, replying in rich detail that I'd scribble for future reference.

Among the notes I took were a few sketchy details of Mr. Gregory's photo album that I hoped to one day revisit at length. I've been able to do that this week, enjoying a glorious cross-section of a gentleman's remarkable hockey life collected between leather covers.

Photos courtesy Toronto Maple Leafs/Hockey Hall of Fame

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