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
MLB Teams Whose Playoff Dreams Have Made It Into September
Tue Sep 01 2026
Ranking WWE’s Top 25 Male and Female Superstars of 2026
Mon Aug 31 2026
Latest Betting
- MLB Best Bets: Yankees, Braves and Nationals Amongst Sunday’s Top Picks
- Best MLB Bets Today: Carlos Rodon, Kyle Schwarber Highlight Saturday's Picks
- UFC Shanghai Betting Odds Line Movements Before Saturday
- UFC Shanghai Best Value Bets: Three Method-of-Victory Props to Target
- UFC Shanghai Underdog of the Week: Denise Gomes Is a Major Value Play
- UFC Shanghai Picks: Three Best Bets for Saturday's Fight Card
- Rockies vs. Braves Picks: Two Best Bets for Friday Night

