Jon: If I won the wager of my entire Bodog account, I would celebrate like I won the Stanley Cup.

Garth: So you'd rent out a dressing room and a bunch of half-naked men that you could spray champagne on and kiss a piece of metal with?

I've enjoyed a certain level of success gambling so far during the Stanley Cup playoffs. (see Jon's picks for round 1, round 2 and round 3). With the Stanley Cup Finals on the horizon, I'm at a crossroads. Do I take my modest winnings and cash the cheque, content to watch the finals for the exciting hockey rather than the gambling possibilities? Or do I take everything I have left in my Bodog sports account and dump it into a huge bet on the Chicago Blackhawks?

Of course, I really should have taken my own advice rather than playing it safe last round. Chicago was a 10/11 favourite to win the Stanley Cup at the start of the conference finals. Now, if you take the price with the series spread, they are a 20/31 favourite. But that's the problem with gambling. Looking at past bets and ruing the fact you didn't make them when you could have is folly. Regretting not making a bet is a bad reason to go forward with another without sound reasoning behind it.

I don't believe the Flyers have a shot at winning this series. The Blackhawks have morphed into an unstoppable machine that rolled through a tough Western Conference. The Flyers finished 18th in the league, barely made the playoffs and beyond their miraculous second round come back, had a much weaker run to the finals. First it was a disinterested Devils team, then a Bruins team that did plenty of damage to itself and finally a Canadiens team which ran out of smoke to hide the mirrors they were performing their magic with. The reasons and odds are stacked against the Flyers.

But that's the problem, because this is sports. Both the Flyers and Habs proved this post-season that even when there are a scale-shifting pile of reasons teams shouldn't win on one side of the scale, there is always a marble of probability on the other side that the impossible and unexpected will happen. The question when placing a bet like I'm thinking of doing is whether I want to feel the surge of victory or the crush of defeat, or just sit on the sidelines and be content as a spectator.

Of course I could balance out my problems by making a group of bets instead of one big one, but that wouldn't be as much fun. And really that's what this was all about anyway. I never planned on winning money; that was a nice side effect. I wanted to have more fun watching hockey by being financially tied to it in a ridiculous way.

I'm going to take the Hawks. Let's hope they win in four, five or six games. Otherwise I might have an aneurysm.