Open this photo in gallery Winnipeg Blue Bomber fan Chris Matthew has been wearing shorts daily since the 2001 Grey Cup. JOHN WOODS/The Canadian Press

A casual bet about the Winnipeg Blue Bombers getting the ultimate Canadian Football League win has left one of their most dedicated fans in shorts for the past 18 years.

Chris Matthew has optimistically dusted off his old zubaz print pants from the 1980s in preparation of finally covering up his calves as the team prepares to square off with the Hamilton Tiger-Cats for the Grey Cup on Sunday in Calgary.

“Be careful of what you say, because if you have to live up to it sometimes it can be a little uncomfortable,” Matthew, 62, said with a hearty chuckle.

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The long-suffering fan was dressed in black shorts, a Bombers jersey and light coat standing on his Winnipeg driveway as wet, cold snow fell around him Wednesday morning. The retired teacher recalled the fateful evening a week before the Grey Cup in 2001 when the Bombers had the best record in the CFL.

“I was still wearing shorts at the time and somebody asked, ‘How long are you going to wear those?’” Matthew said.

“I said, ‘Well until the Bombers win the Grey Cup.’ I figured it was a give-in.”

But the Bombers lost 27-19 to the Calgary Stampeders in Montreal.

“I’m still waiting to put pants back on,” Matthew said in a matter-of-fact tone.

Open this photo in gallery Matthew brushes snow from his sidewalk in Winnipeg on Nov. 20, 2019. JOHN WOODS/The Canadian Press

Matthew has a closet full of different shorts to cover half of his legs during the harsh prairie winters. He has worn pants on a couple of occasions to funerals of people who did not know the story of the shorts.

If it’s a formal occasion, he wears his kilt.

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Even when he was still teaching junior high, he wore the shorts to teach the children “don’t go flapping your gums and not back it up.”

“Most people just think there’s something wrong with me and I think maybe they are right,” Matthew said with a laugh.

As Matthew talks about all the activities that seem opposed to a life in shorts – shovelling in a blizzard as an example – his wife of 27 years, Darla Robinson, just shakes her head.

“I laugh every day. He’s ridiculous,” she said.

Open this photo in gallery Matthew holds up the pants he'll wear if the Bombers win the Grey Cup for the first time since 1990. JOHN WOODS/The Canadian Press

Matthew used to wear the zubaz pants almost every day before the bet, she said. The pants are a soft fabric, elastic waistband, wide fit and wild patterns and colours. Think MC Hammer.

“Given the option, I would take the shorts,” she said. “He really likes wearing the shorts. … But he did this out of honour.”

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While Robinson hates the pants her husband is preparing to wear, she is willing to put up with it to end the Bombers’ Grey Cup drought.

The team last took home the trophy almost 30 years ago in 1990, the longest stretch without a title by any current CFL team.

Now that the team is on a playoff roll after taking out the Saskatchewan Roughriders 20-13 in the West final – the couple is optimistic the Bombers’ luck is ready to change.

They will be going to a friend’s home to watch Sunday’s championship – with the pants in tow.

“I really didn’t think I’d be here 18 years later standing in shorts,” Matthew said.