Few chuckwagon drivers have left as large an imprint on the sport and on the Calgary Stampede as legendary driver Tommy Glass did. Those contributions were remembered this weekend as news spread that Glass – an ambassador, commentator and four-time winner of the Stampede’s Rangeland Derby – died. He was 77.
Calgary mourns the loss of a legend
“Today, Calgary lost a legend,” said Calgary Mayor Jeromy Farkas. “Tom Glass was one of the greatest chuckwagon drivers our city has ever known. His achievements on the track earned him a place among the icons of the Calgary Stampede, but his impact reached far beyond competition. He was a respected mentor, ambassador, and proud steward of our western heritage.”
Glass died just days before the 2026 edition of the Calgary Stampede, an event he helped define for decades. A look through the archives of the Calgary Herald, the Calgary Sun and the Calgary Albertan reveals dozens of photos, columns and sports stories reflecting the cowboy beloved in Alberta.
Memorable photos from his career
From his early wins to quiet moments in the barns, the images capture a life dedicated to chuckwagon racing. In 1981, Glass celebrated a Stampede win with teammates. The Calgary Herald sponsored his wagon for many years, and in 1985 he was pictured rounding the barrels. In 1987, he and his team celebrated another Stampede victory. A 1989 photo shows him washing down one of his horses, while another captures a quiet moment at the barns.
In 1995, Glass won the North American Chuckwagon Championships in High River, waving to the crowd after crossing the finish line and later smiling as he received his cheque and belt buckle. A 1997 photo shows Jason Glass and his father Tom, part of four generations of championship-calibre drivers. That same year, Buddy Bensmiller edged out Glass in Heat 8 of the Rangeland Derby, and Glass raced the Stampeder Exploration Ltd. wagon to the finish line on the final Saturday.
Family and parade honors
In 2003, Iris Glass became emotional as she and her son Tom took centre stage at a Calgary Stampede preview luncheon, where the Glass family was named parade marshals. They later rode through Calgary streets aboard their well-known checkerboard chuckwagon during the 2003 Stampede Parade.
The Stampede also kept a memento in its archives: a straw hat Glass wore in 1988, with duct tape inside the brim, a testament to his practical cowboy spirit.
Headlines spanning decades
Tom Glass made headlines many times over the decades. The Calgary Herald featured him on July 8, 1980; the Calgary Albertan on July 11, 1980; and the Herald again on July 14, 1980, June 13, 1981, July 9, 1983, July 18, 1994, July 13, 1997, June 13, 1998, Aug. 2, 1998, July 17, 2011, and July 11, 2023.
His legacy as a four-time Rangeland Derby champion and ambassador for the Calgary Stampede will be remembered by fans and fellow drivers alike. As Mayor Farkas noted, his impact reached far beyond the track.
