One of the two longest current Grey Cup droughts is guaranteed to end. Hamilton hasn't won it in 20 years. Winnipeg hasn't won it in 29. And remember the CFL is only a nine-team league (eight until Ottawa got an expansion team in 2014). We all like to make fun of the Leafs for going 52 years without a Stanley Cup, but at least they're competing with 30 other teams.
The Bombers have the weirdest fan. Back in 2001, a guy from Winnipeg named Chris Matthew promised to wear shorts until his team won the Grey Cup. The game was only a week away and the Bombers had the best team that year, so he figured it wouldn't last long. But here we are 18 years later and he's only put on pants for a few funerals. He has a kilt for formal occasions, but he swears he keeps the shorts on even when shovelling snow in those brutal Winnipeg winters.