Gainey's $100 suit stitched into Canadiens' Stanley Cup lore

MONTREAL -- Bob Gainey’s Montreal Canadiens mug shot is atop the small, single-column ad in the Montreal Star of March 11, 1976, in which the future Hall of Famer has a word of advice for the fashion-conscious man:

“Bob Gainey says: ‘A Spring Suit from Tony the Tailor Scores High in Styling and Quality. If you want today’s look in suits, or in leisure wear, go to Tony’s. You will have a great selection to choose from! Tell him Bob sent you.’ ”

Six weeks later, a similar ad for the popular Montreal haberdasher appeared in the Star, this one featuring veteran Canadiens forward Jim Roberts. On May 6, the Tony hat trick was completed by their teammate, rookie Doug Jarvis.

A half-century later, Gainey studies a copy of his ad and rewinds to a very different time in the NHL.

Canadiens teammates and Peterborough Pete alumni Bob Gainey, Jim Roberts and Doug Jarvis in their Tony the Tailor newspaper ads that appeared in a two-month span, March-May 1976.

“The three of us were playing together, and all of us had played for the (major-junior) Peterborough Petes,” Gainey said on Friday, sipping a cappuccino before setting off from Montreal on the drive back to his Ontario cottage-country home.

The late Roberts was 13 and 15 years the senior of Gainey and Jarvis and had been in the NHL for a decade, with the Canadiens and St. Louis Blues, before his fellow Petes would arrive in Montreal.

“Jimmy likely already had a connection with Tony, so he took Doug and me along with him one day to the shop in Old Montreal,” Gainey said. “We made a deal that day and we all got suits for about $100 each.”

In a very short time, the three would be styling their Tony the Tailor suits, looking snappy indeed during the Canadiens run to their 1976 Stanley Cup championship that culminated with a four-game Final sweep of the two-time defending-champion Philadelphia Flyers. It was the first of four titles the most recent Montreal dynasty would win consecutively.

“There might have been some plaids,” Gainey said brightly, quizzed on the trio’s new threads.

Montreal Canadiens great Maurice “Rocket” Richard in a 1952 newspaper ad for Tony the Tailor, and wearing a suit from the haberdasher in his Montreal tavern a decade later.

“We weren’t all trying to be Derek Sanderson,” he added of the flamboyant Boston Bruins forward of the 1960s and '70s. “But we were required to wear suits all the time. Some teams required their players to wear suits to their practices. You needed something that was durable because when you went on the road for a few games, you’d take just one suit. Not like today, with guys wearing a different outfit every night.”

Closed decades ago, for a time stitched into a related business, Tony the Tailor was a Montreal institution. Its first advertisement of note was hockey themed, published in the Montreal Star on Jan. 15, 1948.

Four years later, Canadiens superstar Maurice “Rocket” Richard posed in a newspaper ad which trumpeted that wearing one of Tony’s suits had ranked him among Canada’s 10 Best Dressed Men.

Full-page “meet the team” Montreal broadsheet newspaper promotions for the Canadiens, Major League Baseball's Expos and the Canadian Football League’s Alouettes would be hugely popular over the years, wallpapering the bedrooms of young fans. Mug shots and thumbnail biographies of players and coaches were anchored with the names of local businesses; traditionally, Tony the Tailor was the marquee sponsor, attached to the Canadiens coach -- first Dick Irvin Sr., then Toe Blake and Scotty Bowman.

One-third of the Montreal Gazette’s full-page “Good Luck Les Canadiens” ad published on April 10, 1976, similar pages appearing through much of the 1960s and 1970s. Coach Scotty Bowman (far left) is sponsored by Tony the Tailor; Bob Gainey (sixth from left) by a courier. The Canadiens would win the Stanley Cup the following month, and three in a row after that.

“The thrill you get when the puck-carrier breaks clear is no greater than the thrill you get in being tailored by Tony,” the 1948 ad read. “There’s no interference when you look and feel right. … The cutting and tailoring are refereed by Tony himself, and when he finishes the finished product, it scores a sure win.”

Eleven months later came a splashy ad announcing an open house at Tony’s new location, on Notre Dame Street in Old Montreal, custom-made suits priced at $60 and $65. It’s here in 1976 that Gainey and his friends dropped in to be sized up by a tape measure.

This wasn’t a sponsorship per se for the three, anything earned on the side rare in those days but for the biggest stars in the game.

“We just got a good price on a suit,” Gainey said. “I might have gone back another time or two. It was more of a fun thing that the three of us did because of our background together.”

Tony the Tailor announces an open house at his new Montreal location in a 1949 newspaper advertisement.

Tony the Tailor was steeped in hockey tradition by then. Bowman, coach of the 1970s Canadiens dynasty, remembers center Ralph Backstrom boarding with his father, John (Jack) Bowman, during Backstrom’s first couple of seasons in Montreal during the late 1950s.

“Players would go Tony the Tailor for their suits,” Bowman recalled. “If they were featured in a Montreal Forum program or a newspaper ad for Tony’s, they were good for a free suit. Ralph took his first Canadiens paycheck to Tony’s and had three suits made. He brought them back to my dad’s and showed them off, asking which one he liked best.

“My dad replied, ‘They’re all beautiful suits, Ralph, but you can only wear one at a time,’ ” Bowman said, laughing. “That’s the way men were in my dad’s day -- you wore your suit until it wore out, then you bought a new one. You owned one pair of shoes, and you replaced them when they wore out.”

Gainey made very little money on the side during his playing career that saw him win the Stanley Cup five times and play his entire 1,160-game career for the Canadiens between 1973-89, skating another 182 games in the playoffs.

Bob Gainey accepts the 1981 Frank J. Selke Trophy as the NHL’s top defensive forward from Frank Selke Sr. Gainey won the award the first four years it was presented.

A Class of 1992 Hockey Hall of Fame inductee, Gainey would go on to serve as Montreal’s general manager and coach, then as GM guide the Dallas Stars to their 1999 Stanley Cup win. His portrait is displayed in the Canadiens dressing room among those of other franchise players similarly enshrined.

Voted winner of the Conn Smythe Trophy as MVP of the 1978-79 postseason, Gainey was awarded the Selke Trophy, voted the NHL’s best defensive forward the first four years it was presented (1978-81) and in 2017 was voted among the 100 Greatest NHL Players for the League’s Centennial year.

His No. 23 was retired to Bell Centre rafters in 2008, and on Friday he laughed about the coincidence of having parked his car around the corner from a Montreal-suburban coffee shop directly in front of a building whose street address was a gigantic 23.

Gainey reflected on having wanted to buy a car during his playing career and Canadiens defenseman Jacques Laperriere sending him to his agent.

“I went to the agent's office and he said, ‘Some of the guys get deals with car dealerships, do you think you’re interested in that?’ Well, what did I know?” he said.

Bob Gainey watches the action from the bench during a Montreal Canadiens game against the New Jersey Devils on Oct. 16, 1987, at Brendan Byrne Arena in East Rutherford, New Jersey.

“He said, ‘When you’ve been on the road for a couple days, this dealer will want you to come in and sign autographs in his showroom. A lot of the players don’t want to do that, they’d just as soon pay for their car.’ So he sent me to a guy and I bought a car.

“Team management didn’t like the whole concept (of money earned on the side). Scotty came in the morning of a game and found out a couple of the guys were at an arena signing autographs and he wasn’t happy. ‘People don’t want to see that, it’s too commercial, they want to see the athletes,’ ” he said.

When fans did see their well-dressed favorites outside the Forum, walking to or from their cars parked around the arena, or riding in convertibles in one of their many Stanley Cup parades in the 1950s, '60s and '70s, chances are that Tony the Tailor’s logo -- a stylized T below a knight in armor -- was stitched inside on the jacket’s breast pocket.

Top photo: Bob Gainey with his 1976 Tony the Tailor ad on Aug. 14, 2026 at Les Delices de la Gare in Pointe-Claire, Quebec.