Thou shalt not hedge?

I have a longstanding bet with my friend that has grown over the last 6 years. He's a Toronto Maple Leafs fan and I guess if I had to pick a team I'd cheer for it would be my hometown Canucks. 5 years ago we were playing golf and he went off about how the Leafs were a much better team, had better management, better prospects, etc... and that they would have a better record than the Canucks at the end of the season. This went back and forth until we ended up with the following bet: Which team would win the Stanley Cup first?

We put $100 on it and knew there was a good chance the bet might not be resolved for a long time. The following year we were talking about the bet again and he said that the Leafs were even CLOSER to winning the Cup and that the Canucks were on the decline. I asked if he wanted to raise the bet to $200 and he said yes. So, here we are 6 years later and the bet currently stands at $2,500. The best part about this is that although the Canucks haven't made much of a run in any of these years, the Leafs haven't even made the playoffs ONCE. You can imagine that I've felt like I've had the upper hand every year going into the playoffs.

So, the Canucks have just won Game 1 of the Western Conference Final and they are 3 wins away from going to the Cup Finals. I'm not a sports bettor at all (it almost seems that if I've ever made any kind of a sports wager the opposing team wins 90% of the time or more). Assuming that the Canucks make it to the Finals, I'm wondering if anyone can think of a wager (or some kind of weird parlay) I can make that will bring me a return of MORE than $2,500.

Keep in mind that if the Canucks win the Cup I make $2,500 and if they don't it has cost me nothing.

Just put your money on Tampa Bay!

Since it started at just $100, perhaps you could let your friend of the hook ! Ask him how much he is willing to pay you to call off the bet. It's what I would do.

He's a Maple Laughs fan, he deserves to get gouged, especially if thinks they are well run or well organised. They've been a joke for a while, and their revolving door policies are tragic.

Surely just lay off other side if the Nuckleheads make the Final. That way you win which ever way.

My comment is that your friend must be absolutely stupid to even consider betting the Leafs over the Canucks in any kind of wager. The Canucks have been a much better team for a very long time and they've had a good shot at the cup for the last few years.

I would absolutely ask him how much he's willing to pay you to call off the bet.

I've already (half-jokingly) offered to let him buy out the bet but he would rather ride it out and pay up than admit defeat just to save a few bucks. He's got plenty of money so that isn't a concern; he's just a die-hard Leafs fan as most guys who grew up in Niagra Falls back in the 60's seem to be. He also knows the Canucks have never won the Cup so he figures there's still a very good chance he won't have to pay anything at all... for this year at least.

What I'm wondering is if there's any way to parlay the potential $2,500 win into a larger win by finding some kind of odds come the finals.

Don't listen to thecesspit, he's an admitted loather of Leafs. =p

I, on the other hand, tout the Leafs as the be all, end all of all that is hockey. That being said,.....thecesspit is spot on lol. There is no way your bet could end badly. Want to turn it into more than $2,500? Simply keep on raising the bet yearly as you have been. The only reason for cashing out early is to spare your friend a financial disaster. I am in no way qualified as a sports better, forecaster, or any other type of predictor, but I'd say your friends belief ranks up with a belief that the Lions will win a Superbowl this decade, or that baseball will be interesting in my lifetime, or that Nareed will wax poetically in his new blog extolling the virtues of soccer. Sure, it's POSSIBLE. But I think the answer to the actual probability of it happening can be found in the thread discussing the definition of 'infinitesimally small'.

I bleed blue and white, but even I can admit your sitting on money in the bank. Unless you think too hard (like us Leafs fans do) and realize past results MAY affect future decisions in sports, and since the Leafs haven't won since '64, it's just GOT to happen THIS YEAR......

Quote: DeMango

Just put your money on Tampa Bay!

The Canucks are going to choke (Sorry, that's what they do). So I will +1 DeMango.

wait till we are down to two teams and one of them is Vancouver. Then Lay off a Grand on the other team. The WoO has said hedging can be permissible in sports betting I believe, and since this guarantees you some money it seems smart.

PS: since making that hedge bet would mean a trip to Vegas for someone like me, I'd be pretty happy about it if your team makes the finals.

I see a flaw in the hedging aspect. Two scenarios will happen:

1. Canucks win, team XYZ loses.
a) Win $2500! The bet is over.
b) Lose, say, $500 on the hedge bet.
c) Total profit: $2000

2. Canucks do not win, team XYZ gets the cup.
a) Win, say, $1500 on the hedge bet.
b) The "friendly" bet is still not over! It could increase to $3000, $5000, $10,000... and you could potentially LOSE. (Of course, you might also win!)
c) Profit or loss is unknown.

If situation 2 occurs, it's not really that you hedged your bet, because you do not necessarily have an opposite outcome. Make sense?

You ask how you can bring in more than $2500 and without risking more I don't see how you can do that. However you could, as others pointed out, hedge your bet and lock in a certain profit. Personally, I'd probably lock in at least $500 on the other team in the Finals.

Quote: FinsRule

The Canucks are going to choke (Sorry, that's what they do). So I will +1 DeMango.

The Nucks have got to the conference finals. Even a loss now wouldn't be a choke. Unless they get up 3-0 and lose 4-3 in either of the series.

Choking is what the Caps did.

Quote: thecesspit

Choking is what the Caps did.

I'm a Caps fan, still I can't deny it.

Some salve from that wound would be seeing Tampa whip Boston then do well in the Finals, if not outright win the Cup. Seems a distinct possibility.

Quote: Face

Don't listen to thecesspit, he's an admitted loather of Leafs. =p

... but I'd say your friends belief ranks up with a belief that the Lions will win a Superbowl this decade,....

Touche... I'd be willing to bet though that the Lions make a Conference finals before the Leafs. I have hopes that this could be a good decade :)

Quote: thecesspit

Touche... I'd be willing to bet though that the Lions make a Conference finals before the Leafs. I have hopes that this could be a good decade :)

Doh! I forgot it was you who liked the Lions. Ha! That wasn't an intended jab, sir, just a humorous coincidence. Here's to hope. =)

Quote: Face

Doh! I forgot it was you who liked the Lions. Ha! That wasn't an intended jab, sir, just a humorous coincidence. Here's to hope. =)

Oh I wouldn't blame you for the jab after my repeated slaps at the Leafs. :)

Quote: thecesspit

Touche... I'd be willing to bet though that the Lions make a Conference finals before the Leafs. I have hopes that this could be a good decade :)

I bet the Lions making the Conference Finals every year. Of course it's pretty much a loss by week four but one of these years!

Well, TheNightFly....is the excitement building? I'm admittedly rooting AGAINST you, for us Leafs fans endure enough disappointment without adding this to the list, but I am curious. A 6 year bet may well be coming to fruition, I wonder if your friend is peeing himself yet?

Nah, he just keeps telling me how good it is for Canucks fans to see their team get to the Cup Finals (2 weeks ago he said the same thing about the Conference Finals...). He's got plenty of money so that isn't an issue but I know it will stick in his craw mightily if the Canucks do win. He's already telling me about how good the Leafs are going to be next year. I've seen only about 2 games live in my life but I might just splurge and buy a ticket if it gets to a game 5. Perhaps by then I'll have become a little more interested in the outcome beyond the wager in question.

At leat the Canuknucleheads are in the Cup finals. Tell your friend "Bite Me". LOL

But then I'm just a disgruntled NYR fan.... :P