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The Bet

A tale of love and war and hockey.

Note: This article is a blast from the past, from 2015.

I became a homeowner in September 2008. We had an infant son and wanted to get out of the frozen wasteland that was North York. We found a small house across the lake in a neighbourhood that was entering the gentrification phase of its life.  Once we were moved in, a plan was devised. Beginning with the 08/09 NHL season our porch became a focal point for the Leafs/Habs rivalry on our street.

The Bet: When the teams play each other, the winner’s flag hangs over the house until the next game.

The first game in our new house was an important moment. Who would hold the honour and bragging rights? Toronto began their season vs Detroit as the Red Wings hoisted their Stanley Cup banner to the rafters, and won 3-2 defeating the Cup champions on their special night.  Montreal began the year in Buffalo (as some sort of punishment I assume) and lost in a shoot out 2-1. The next night was the night we were waiting for, October 11th, 2008. Family was down from Montreal for the first thanksgiving in our home. Habs fans, Leafs fans, together for such historic game, and they were treated with: Montreal Canadiens 6 – Toronto Maple Leafs 1

I should have seen that coming.

The next morning, in full daylight, I was on the porch in my Leafs sweater, hanging that damn flag up, out in front of the world.

The Leafs would have their revenge, defeating Montreal 6-3 on November 8th.

We’ve had flag changes, thefts (Habs fans practicing their looting stole the flag & pole one night) and, as you can see below, vandalism.

flag dick

I do have to give Lady points for creativity following a playoff sweep of the Lightning

flag broom

That’s how the seasons would go. Win, loss, trash talk, win, vandalism, loss. The neighbours enjoy it, we have one who waits on game nights to cheer (Montreal) or boo (Toronto) when the flag changes. Psh. Canucks fans. It’s an invitation for discussion, "Man I hate that thing up there" "damn Leafs", shouts from cars as they pass.

The total score up to this season sits at:



Days flying







2008/09 – TOR 3 -117 – MTL 3 -65 – Playoffs - 11
2009/10 – TOR 3 -49 – MTL  3 -145 – Playoffs 44
2010/11 – TOR 3 -151  – MTL 3 – 37 – playoffs 18
2011/12 – Tor 3 – 142  - MTL  3 – 46
2012/13 – Tor 3 – 53 – playoffs – 4 - MTL 2 – 45 – playoffs 12
2013/14 – Tor 2 – 102 – MTL 3 – 94 – playoffs 43

This year we’ve seen the longest gap between Leafs/Habs games since this all started. A 4-3 loss (that turtleneck wearing motherfucker Plekanec scored with 43 seconds to go) to begin the season on October 8th and now we've waited 129 days for revenge (the previous longest streak was for the Maple Leafs, 107 days in the 11/12 season). This gap has given Montreal the edge in the day count and now sit at 689 days. 129 days of a Canadiens flag flying outside my home. 129 days of taunts every time I try to walk in my front door. 129 days of the wind blowing it into my face. 129 days.

Could we add another 14 days on top of that? Judging by recent events (13 Maple Leafs losses in 14 games, their only win over the lowly Oilers) it would be a safe bet to say yes. But Montreal is reaching over its head lately if you listen to the numbers. If the Leafs can keep this game close, the Habs have to regress on their 1 goal victories eventually, so why not tonight? I hate to rely on hope and luck, but in a game this big, in a town so smug, in a rivalry this old, and with a team this unlucky, hope is all I have.

Come on Leafs. Pull off a win in 2015 and make it one that counts, at least to this fan.