If I’ve learned anything from professional wrestling, it’s that I should never admit to watching professional wrestling. If I’ve learned a second thing from professional wrestling, it’s how to plan and market a serious storyline (see: my constant threats to turn on people or deliver Sweet Chin Music to people’s families, friends, etc). But if I’ve learned a third thing from professional wrestling, it’s that friendships never last.

Shawn Michaels turned on Marty Jannetty for greater individual fame. ‘Macho Man’ Randy Savage turned on Hulk Hogan over a woman. Christian turned on Edge out of professional jealousy.

And now, for a greater role at The On Deck Circle, Alex Pennycook has turned on Stu Wilkinson.

These two behemoths (each measure in at roughly 6’7”) have been best friends for four years now, sharing a residence building in first year and living together at 29 Clergy St. W (vandalism encouraged) for the following three. They get along well, mostly based on their love of sports. But beneath the surface things aren’t as friendly as they seem.

Both men are bitter at being grouped together as a tall house (Josh is also pushing 6’5”) rather than having their individual heights acknowledged. They have battled for four years (8 seasons) for the position of primary big man on the Comm 08 intramural basketball team. They have an intense Madden rivalry, conflicting beliefs on sports, and argue about whether America’s Funniest Home Videos or The Real World is the perfect commercial break fodder for sporting events. They also fight endlessly for my love, but that’s a story for another time.

Today though, this superficial getting along has been thrown by the way side. Looking at Stu’s putrid performance on The ODC’s Shoe-In of the Night (3-8…and these are supposed to be shoe-ins!), Alex, an avid sports gambler, has challenged Stu for the spot. Alex thinks he can provide better sports gambling tips, do it more reliably, and come up with a better gimmicky name than Stu’s Novelty Sized Shoe-In of the Night.

“Stu has proven time and time again that the best gambling strategy is to pick against his lock of the day/week/month/year,” Alex quipped, obviously referring to how our 3-man gambling team fared better betting against Stu during the football season.

Stu was not taken aback by the challenge, long assuming that Alex was jealous of his ODC Sidebar spotlight. Stu doesn’t think he can be beaten.

“I’m not here to toot my own horn — I’ll let my results do all the tooting for me. But what I will say is that I used to be the best forecaster at Queen’s University. That kind of talent doesn’t dissapear overnight,” Stu emphasized.

Alex, though, knows he can take down his housemate and in-the-paint compatriot. Pennycook looks at the challenge as a matter of utmost importance for their relationship, this website, and the world, explaining, “For the good of mankind, I’ll take him down so that people will no longer be subject to his awful picks.”

So what was I to do when two of my best friends got at each other’s throats with the site’s reputation on the line? Well, like I said, Vince McMahon has taught me well how to promote a showdown. It is with the great Vinny Mac in mind that I present to you: The On Deck Circle’s $100 Sports Gambling Challenge.

That’s a shorter title than the original The On Deck Circle.net’s Amazing 6’6” and Taller $100 Do It However You Can Sports Betting Spectacular, so thank me for that.

What is this challenge? It’s simple: each man has one week to gamble $100 to the best of their ability, starting tonight and ending on Sunday. They are free to bet on games straight up, with spread, over/under, and even parlays (multiple-game bets with higher payoffs). They are to provide me with their picks each day for posting in the Shoe-In section of the sidebar, and I’ll keep track of their progress there. A winner will be determined on Monday morning, with whoever has more money left (or made, if you’re optimistic) becoming the new Shoe-In operator.

Stu didn’t really like my idea, but not out of fear. He just doesn’t think Alex is a legitimate challenge, explaining, “I respect Alex as a person, but not as a gambler. How can I respect a guy who routinely bets on the Cleveland Browns? In this crazy mixed up world we live in there are very few constants, and one of those constants is the Browns sucking. It’s science, folks.”

Alex had a favorite team related jab of his own, “3 and 8? Imagine how badly he’d be doing if Pirates baseball had started!”

This is truly one of the greatest storylines we’ve had here at The ODC. From me writing a week in review column drunk to Trevor and I taping a 23 minute Podcast in roughly 23 and a half minutes to January’s behind-the-scenes ODC Royal Rumble (I won, of course), this is truly the most compelling non-sports story we’ve had. Two best friends turned against each other with literally nothing of value on the line. If anything, the winner gets the pain and annoyance of having to submit picks every day, something Stu has struggled with already (he has picked 11 games, and I’ve filled in for 10). But with pride and competitive friendship bragging rights on the line, things can get really ugly, really quickly.

Stu has taken it there from the outset, opting not to lay down a bet tonight. He will instead employ Game Theory, assuming Alex will perform poorly and he can win with a profit of 0. If he does this for more than three days though, he will be disqualified, but it’s a statement strategy out of the gate, for sure.

Alex, confident in his abilities, has gone the opposite route and laid down $20 for tonight. $10 goes to the Boston/Washington NHL game, where he has bet there will be more than 5.5 goals (pays $10), and the other $10 goes to the hapless Philadelphia 76ers -2.5 against the equally hapless Los Angeles Clippers, in Los Angeles (pays $9.09). Tomorrow morning, Alex could have anywhere from $80 to $119.09 where Stu is guaranteed $100.

How will this all shake down? I know three things. Foremost, each guy will forget to send me their picks at least once. Second, Alex will win. And finally, on Monday morning when I crown a winner, there will be Edition #4 of Point, Counter-Point in a best-of-7 series between the Twin Towers. Both men are ready and dedicated, and Stu left us with this:

“To completely rip off the film ‘Two For The Money,’ all I do is hit jumpers and pick winners. And I’m tired of hitting jumpers.”

In the immortal words of Michael Jordan, llllllllet’s get ready to gamble.