‘He played in the first Classic’: Pelling family proud of Rider legacy

Labour Day weekend in Saskatchewan is built around football, and for one Regina family the game comes with a legacy stretching back nearly eight decades.

Bob Pelling wore No. 66 for the Saskatchewan Roughriders from 1946 to 1953, suiting up in a period when the team was just beginning to build its identity. Among his highlights was the inaugural Labour Day Classic at Taylor Field in 1949.

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Historic Saskatchewan Roughriders 1951 Grey Cup program and roster sheet saved by the Pelling family.

A preserved game program and team lists from the 1951 Grey Cup between Saskatchewan and Ottawa sit among the Pelling family’s archives. (Jacob Bamhour/980 CJME)

“He played in the Labour Day Classic, which was in 1949,” said Bob’s son Drew. “So we’re looking at 76 years ago, and it was the first Labour Day Classic in Regina.”

The era was far different from what fans experience today. Players often juggled full-time jobs and earned little for their time on the field.

“Obviously it was for the love of football, and you had to have a full-time job,” Drew said.

“His first few seasons they got paid $100 a season. And then in 1950 they got paid $500, and in 1951 I believe it was $750.”

Vintage Saskatchewan Roughriders team photo in front of Trans-Canada Airlines plane with Bob Pelling.

Bob Pelling (front left) and the Roughriders pose in front of a Trans-Canada Airlines plane. (Jacob Bamhour/980 CJME)

Travel was equally challenging. Most trips were made by train, and the rare flights involved multiple stops.

“In those days, you had to fly from Regina to Swift Current, Swift Current to Medicine Hat, and then on to Lethbridge or Calgary,” Drew explained.

Despite the hardships, Drew says his father never spoke about the game with regret. Instead, he remembered the people.

“He just talked about his camaraderie with the players and everything else and how they just became really good, good friends throughout life,” Drew said.

“A lot of them, they were all local people from Regina and Saskatchewan.”

Drew Pelling wearing vintage Saskatchewan Roughriders jersey number 66, honouring his father Bob Pelling’s legacy.

Drew Pelling stands in his father’s No. 66 Roughriders jersey, a reminder of the family’s deep connection to Rider history. (Jacob Bamhour/980 CJME)

That community connection continued off the field. Bob was heavily involved in local organizations, first with the Kingsmen and later with the Shriners, eventually serving as potentate of the Wawa Shriners Temple. Drew recalls watching his father ride his BMW motorcycle in parades as part of the Shriners motor patrol.

One of Bob’s proudest moments came later, when his grandson Mike Mahoney carried on the football tradition. Mahoney played university football at McGill before a CFL career that included stops in Toronto, Calgary, Saskatchewan and Winnipeg.

“My dad was always really proud that his grandson became a Roughrider,” Drew said.

A past newspaper feature captures the Labour Day football connection in the Pelling family, linking generations of Rider pride. (Jacob Bamhour/980 CJME)

Though Bob died in 2008, the Pelling family still holds Rider season tickets that date back to the 1950s. Drew and his sister continue to attend games, honouring the legacy of the man who once lined up in the Riders backfield.

From that first Labour Day Classic in 1949 to this weekend’s games at Mosaic Stadium, the Pelling name remains part of Rider history — a reminder that football in Saskatchewan is as much about family and community as it is about the scoreboard.