This Is What Happens When You Bet On The Maple Leafs
That fellow up there is Josh Lewis, the sports editor for the Estevan Mercury, in Estevan, Saskatchewan. Josh is a big Leafs fan. Big enough to think they would beat Boston. Big enough to wager a walk of shame on it, complete with sandwich board.
For a while, it looked like the Leafs would win! Josh would win too. But you know how that went.
Josh had to stand along the town's busiest road for a half-hour, wearing this. But Estevan's not a big place, so that's getting off pretty lightly. Josh's co-worker Chad, who won the bet, sent us a pair of photos, in the hopes that we, the citizens of the internet, could share in Josh's humiliation.
Point and laugh! Laugh at the silly man who had confidence in the Leafs!
Latest
Top 10 NFL Player Prop Bets for NFL Week 13
Sat Nov 29 2025
NFC West Power Rankings: Rams Lead the Pack in Week 13
Sat Nov 29 2025
Lane Kiffin’s Future Hangs Over Ole Miss After 11-1 Season
Sat Nov 29 2025
Why the Detroit Lions Were Thanksgiving’s Biggest Losers
Fri Nov 28 2025
Latest Betting
- NHL Prop Picks Today: November 28th's Top Hockey Prop Bets
- Philadelphia Eagles vs Chicago Bears Prediction: Week 13 Betting Picks & Spread Analysis
- College Football Rivalry Week Picks: Best Bets and Expert Predictions for Week 14
- 2025 NFL Week 13 Thanksgiving Betting Preview: Top NFL Bet Picks
- Top Thanksgiving NFL Player Props: Jahmyr Gibbs, Patrick Mahomes, Ja’Marr Chase Picks
- Tuesday November 25th Best NBA Betting Picks, Predictions
- Edmonton Oilers vs. Dallas Stars Betting Pick: Nov. 25th Best NHL Bet

