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Four-time world champion Jason Glass comes from a long line of chuckwagon driving champions: he`s the son of four-time Stampede champion Tom Glass, the grandson of four-time Stampede champion Ron Glass and great-grandson of three-time Stampede champion Tom Lauder, who competed in the very first chuckwagon races here in 1923. Chuckwagon driver Jason Glass participates in the opening day of competition at the Calgary Stampede in Calgary , Ab. Friday, July 5, 2013.Kevin Van Paassen/The Globe and Mail

For a Calgary Stampede threatened by floods and revived on tradition, this is how it has been almost since the beginning: Back behind the Stampede track's far straightaway, just outside of Barn H, a wooden chuckwagon sits painted in a familiar back-and-white checkerboard pattern.

It belongs to four-time world champion Jason Glass, the son of four-time Stampede champion Tom Glass, the grandson of four-time Stampede champion Ron Glass and great-grandson of three-time Stampede champion Tom Lauder, who competed in the very first chuckwagon races here in 1923.

In the history of the Rangeland Derby, known as the sport's Half-Mile of Hell, no one has swallowed more dust, chewed on more mud, or won and lost more than the Glass clan, Alberta's first family of chuckwagon racing.

The Western spirit runs through them as deeply as it does the Stampede and the city that has staged it for 101 years.

"This is what we do," said Jason Glass, taking a break from tending to his 20 horses stabled for 10 days of competition.

"Calgary is the showcase where all the money is, the sponsors, family, people from around the world, and I thank them all. … We weren't going to miss it."

When a June monsoon forced rivers to spill and homes to be evacuated in southern Alberta, Jason Glass took his horses from his ranch in High River and high-tailed it north.

If Calgary was a go (it took two weeks of frantic restoration efforts to ensure it was), then so was he. So was his dad.

Tom Glass, who drove the checkerboard wagon for close to four decades, found his home five kilometres east of Black Diamond suddenly an island in the Sheep River.

He had to take a boat to get in and out of his house. At 64, he no longer races chucks but works as a television commentator for CBC.

"I never pushed Jason [into racing]. It just happened naturally," said Tom Glass, who was featured on the Stampede's 1988 poster. "You grow up around horses and the sport and it's bound to happen."

Much has happened to the Glass family. The checkerboard trademark, their coat of arms, was born of a horse kicking in part of the wagon Ron Glass was using. He and his wife, Iris, found a piece of wood in a ditch one day and used it as a patch. The wood piece was checkerboard in colour so the Glasses painted the rest of their wagon to match it. That was some 60 years ago.

In that time, a Glass has won everything there is to win in a sport where four wagons and their outriders weave their way around an infield of barrels before galloping off in a thundering mass. The family has lost much, too.

In 1971, Rod Glass was an outrider at the Calgary Stampede and killed during a wagon crash. He was 18. An award in his name is presented annually to the most improved outrider. Driver Richard Cosgrave, who married into the Glass family, was killed at a Kamloops rodeo in 1993. He was 37. An award in his name is presented to the chuckwagon driver with the best aggregate time over the Stampede's duration. Jason Glass, 42, has won both the Rod Glass and Richard Cosgrave Memorial Awards.

"I'm not going to say it's easy. It's been hard on everyone in our family," said Jason. "We all know it's a dangerous sport. We understand that. But we love horses and we love the lifestyle. We move on."

The cowboys and chuckwagon drivers are the last remnants of a bygone era, yet what they embody – the determination to confront all challenges – typifies what the Stampede was built on and what this Stampede has tapped into. That Jason Glass could be added to the list of Stampede chuckwagon champions would be ever so fitting.

"The world championship is cool, but it doesn't get you $100,000," said Tom Glass, referring to the winner-take-all finale that features the Stampede's top four wagons. "When I won it the first time, I got $20,000. The next three times I won it, I got $50,000 [for each victory]. I built a house with the first $50,000. The next two, I bought 300 head of cows. It's life changing."

Asked for their favourite Stampede moment, Tom and Jason Glass tabbed the same one. It was when both father and son competed in their checkerboard wagons with a shot at the last day's big money. Tom said he always liked to pull, even with his son's wagon, then holler at him to distract him, only it didn't work. "He was concentrating so hard he didn't hear me."

Jason added something else. "Neither one of us won."

It was a rare day in Stampede history.

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