Toronto Maple Leafs Greatest Ever Christmas Gifts

CHICAGO, IL - DECEMBER 20: A fan dressed as Santa Claus wtaches a game between the Chicago Blackhawks and the San Jose Sharks at the United Center on December 20, 2015 in Chicago, Illinois. The Blackhawks defeated the Sharks 4-3 in overtime.(Photo by Jonathan Daniel/Getty Images)
CHICAGO, IL - DECEMBER 20: A fan dressed as Santa Claus wtaches a game between the Chicago Blackhawks and the San Jose Sharks at the United Center on December 20, 2015 in Chicago, Illinois. The Blackhawks defeated the Sharks 4-3 in overtime.(Photo by Jonathan Daniel/Getty Images)
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Tim Horton, Toronto Maple Leafs (Photo by Bruce Bennett Studios via Getty Images Studios/Getty Images)
Tim Horton, Toronto Maple Leafs (Photo by Bruce Bennett Studios via Getty Images Studios/Getty Images) /

The Toronto Maple Leafs have received many great Christmas gifts throughout the years.

Christmas is a time for giving, and at times NHL general managers play the role of Santa Claus by inadvertently giving away top notch talent for next to nothing in return. The Toronto Maple Leafs hockey team has, throughout its history, been the recipient of such unplanned generosity.

In the spirit of the Yuletide season, let’s look at several examples of key players that the Maple Leafs acquired while parting without much at all.

The players on this list made an immediate impact on Maple Leaf fortunes and made the Buds significantly better. In most cases, the players on this list were watershed acquisitions that helped to define an era. All have gone down as among the finest who have ever donned the blue and white.

The Toronto Maple Leafs Best Christmas Gifts

5. Bill Derlago and Rick Vavie

Acquired during the destruction of the highly talented late 70s version of the Toronto Maple Leafs, centre Bill Derlago and right winger Rick Vaive provided Maple Leafs fans with some measure of hope for the future despite the fact that their hockey team was being torn apart before their very eyes.

Following up on the trade of star winger, Lanny McDonald, to the Colorado Rockies,  Leafs general manager Punch Imlach continued his dismantling of the Leafs roster by trading the popular left winger and enforcer, Tiger Williams, along with Jerry Butler, to the Vancouver Canucks in exchange for two unknown, yet promising, young Canucks players, Vaive and Derlago.

The youthful pair made an immediate impact with the Toronto Maple Leafs and quickly became bonafide NHL stars. Vaive became an elite power forward before that term was even coined with big hits, fights and plenty of goals. He scored 33 in his first full season and notched over 50 in each of his next three campaigns. Vaive’s mark of 54 goals still stands as an all-time season high for a Maple Leaf.

Vaive’s centerman during those seasons was the much underrated Derlago whose playmaking skills had a significant part to play in Vaive’s scoring success.  Unfortunately for Vaive, Derlago, and Leafs Nation, there was very little else besides the aging Borje Salming in terms of support, and Leafs fans had to endure years and years of losing hockey.

As bad as the Buds were during the 1980s, they would have been downright abysmal without the contributions of Vaive and Derlago.

Canadian professional hockey players  . (Photo by Robert Riger/Getty Images)
Canadian professional hockey players  . (Photo by Robert Riger/Getty Images) /

4. Max Bentley

Max Bentley was a slick centre from Delisle, Saskatchewan who was known as the “Dispy Doodle Dandy from Delisle” for his tremendous skating and puck handling abilities.

Bentley and his brother Doug became stars for the Chicago Blackhawks in the early 1940s. Max, in particular, stood out for his exceptional stickhandling skills which he could employ at top speed. For the Hawks, he was sort of a 1940s version of Denis Savard. Bentley was a legitimate superstar in the NHL, so it’s a wonder that he was available for acquisition in the first place.

Bentley join the Toronto Maple Leafs on November 2nd, 1947, along with Cy Thomas in a massive seven-player swap that saw Gus Bodnar, Bud Poile, Bob Goldham, Ernie Dickens, and Gaye Stewart head off to the Windy City.

With the exception of Bodnar, a former Calder Trophy winner, the Buds managed to land Bentley for a package of relative pluggers. The trade that brought Bentley to the Leafs was much like the one that brought Doug Gilmour to the team 45 years later. The Toronto Maple Leafs were able to secure a premier pivot who was a game-breaker and difference maker while maintaining the core of their roster.

In Toronto, Bentley reinforced a roster that was already stacked at centre with the likes of Syl Apps and Teeder Kennedy. Bentley’s presence helped to transform the Maple Leafs into the NHL’s first true dynasty as they continued to win cups with him in 1948, 1949, and 1951.

Max Bentley was elected to the Hockey Hall of Fame in 1966. He is considered widely as one of the greatest Maple Leafs of all-time.

Pavel Datsyuk #13 of the Detroit Red Wings  . (Photo by Jamie Sabau/Getty Images)
Pavel Datsyuk #13 of the Detroit Red Wings  . (Photo by Jamie Sabau/Getty Images) /

3. Red Kelly

Most current members of Leafs Nation will likely know Red Kelly as the historic figure who coached the Buds during the mid to late 70s when the Toronto Maple Leafs enjoyed a brief era of Stanley Cup contention. Kelly might also be remembered as the odd ball bench boss who employed “Pyramid Power” in an effort to push his underdog Leafs past the Philadelphia Flyers, AKA “Broad Street Bullies,” in a quarter-final series when the Flyers were at the height of their nefarious powers.

Few Leafs fans of today are able to remember Kelly’s heyday as a player. Those who can will quickly inform you that Kelly was a superstar and one of the greatest NHL defencemen ever. Kelly initially plied his trade for the Detroit Red Wings and later for the Buds.

Kelly was a solid defensive defenceman, but he, along with Doug Harvey of the Montreal Canadiens, was revolutionizing the role of the blueliner from stay at home defender to puck-rushing, playmaking, offensive contributor. Bobby Orr would complete this transition in the late 60s, but Kelly was in the vanguard of this movement.

Kelly only became available because Red Wings general manager Jack Adams had wanted to trade him to the New York Rangers after learning that Kelly had been hiding an injured ankle. When Kelly refused the trade, Leafs coach Punch Imlach convinced Kelly to join the Buds instead of hanging up his blades as was Kelly’s plan at the time.

On February 10, 1960, Adams agreed to trade Kelly to Leafs for the miniscule price of marginal defenceman Marc Reaume, a player who only played 47 games for the Wings before settling in to the role of career minor leaguer. With Kelly in the fold, the Toronto Maple Leafs were now poised to form the second great Leafs dynasty. On a team that already boasted stalwart defenders such as Tim Horton and Allan Stanley, Kelly was able to switch to forward, a role that was easier on his bum ankle, and this Buds juggernaut captured four more cups in the 1960s.

Thanks, Jack. And a belated Merry Christmas.

TORONTO, ON – SEPTEMBER 22: Doug Gilmour #93 of the Toronto Maple Leafs  (Photo by Graig Abel/Getty Images)
TORONTO, ON – SEPTEMBER 22: Doug Gilmour #93 of the Toronto Maple Leafs  (Photo by Graig Abel/Getty Images) /

2. Doug Gilmour

Doug Gilmour joined the Toronto Maple Leafs in an epic trade that echoed the aforementioned player swap that brought Max Bentley to the Buds in 1947.

It was the early 1990s and the Toronto Maple Leafs were still reeling from the destruction wrought by owner Harold Ballard and general manager Punch Imlach twelve years earlier. Imlach, with Ballard’s blessing,  had traded Lanny McDonald, Tiger Williams, Pat Boutette, Darryl Sittler and Ian Turnbull and left the franchise in shambles.

By Christmas of 1991, a new GM, Cliff Fletcher, had inherited this mess, but he was about to receive a franchise reviving gift from Calgary, the team he had just left,  in the form of Gilmour.

As Fletcher knew, Doug Gilmour had always been a great two-way NHL centre. However, on a deep Flames roster Gilmour was a number two pivot to Joe Nieuwendyk. If Fletcher could package off Gary Leeman with an assorted collection of odds and ends and dangle them in front of his young replacement as Flames GM, Doug Risebrough, he might just be able to wrest Gilmour from the Flames.

On January 2, 1992, just a few days after Christmas, the Toronto Maple Leafs received one the greatest belated Christmas presents in NHL history-Doug “Killer” Gilmour.

In the biggest trade in league history, Leeman, Craig Berube, Jeff Reese, Alexander Godynyuk, and Michel Petit went to Calgary, while Gilmour, Jamie Macoun, Rick Natress, Rick Wamsley, and Kent Manderville came to the Big Smoke.

Maple Leaf fortunes turned immediately.

Yes, Virginia. There is a Santa Claus. He lives in Calgary and calls himself Doug Risebrough.

Nov 9, 2019; Toronto, Ontario, CAN; Toronto Maple Leafs  Mandatory Credit: Nick Turchiaro-USA TODAY Sports
Nov 9, 2019; Toronto, Ontario, CAN; Toronto Maple Leafs  Mandatory Credit: Nick Turchiaro-USA TODAY Sports /

Teeder Kennedy

No other acquisition in Toronto Maple Leafs history compares to this one when applying a cost-benefits analysis. Theodore “Teeder” Kennedy is today remembered as one of the greatest Toronto Maple Leafs ever and arguably the teams’ greatest captain, and he was acquired for next to nothing.

As hard as it is to fathom, Kennedy almost ended up wearing the red white and blue of the arch enemy, the Montreal Canadiens.

During Kennedy’s youth in Port Colborne, Ontario, the Habs had wooed and signed Kennedy, and he had attended a Canadiens training camp.  However, Kennedy had a bad impression of Montreal management and Leafs GM Frank J. Selke was able to secure Kennedy’s rights on February 28th, 1943, in exchange for the journeyman defenceman, Frank Eddols.

The Toronto Maple Leafs, with Kennedy now in the fold, established the NHL’s first true Stanley Cup dynasty. Kennedy, with the help of Syl Apps and Max Bentley, captured the Stanley Cup in 1947, 1948, 1949, and 1951. This edition of the Toronto Maple Leafs was the first team to ever win three consecutive Stanley Cups.

Kennedy was a dogged two-way centerman who was a mediocre skater, but he made up for this shortcoming with excellent puck handling and playmaking abilities. Kennedy’s teammates described him as a player of unequaled determination and tenacity. Some have said that he may have been the greatest face-off man in the history of the NHL.

When Syl Apps retired in 1948, Kennedy was a natural and popular choice to replace him as Maple Leafs’ captain. In all, Kennedy played 14 seasons for the Buds, finally retiring in 1957.

Next. The Top 10 Leafs Prospects. dark

Kennedy has gone down in hockey history as one of the most popular Maple Leafs ever and along with Max Bentley and Red Kelly, he was included in nhl.com’s list of the100 greatest NHL players of all-time.

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