I think I proved last year that I am not afraid to gamble when I bet my hair on the Chicago Bears versus the Green Bay Packers 2007 records. For anyone that has seen me over the past 3 months, then you know the outcome of that bet, and you also see that I always pay up if I lose.

Well, I have a new bet that I am actually very excited about. I have made this prop bet with my good friend and neighbor Jay Sandine. For those of you that may remember, he demoralized me in the 100 yard dash in our street last summer. Now it’s my turn to get even. Clearly after reading this, you will see I am huge favorite to win. But I invite your comments at the end of this post.

The great thing about Chicago is that there is no shortage of professional sports teams to root for. In baseball you can choose between the Chicago Cubs or the Chicago Whitesox. I have been a diehard Cubs fan since I was a small kid. I have been to several games, and yes I have even sat across the street on the rooftops a few times. A few years ago at a pharmaceutical sponsored event, I sat and watched a game with the legendary Ernie Banks. I’ll be honest though, it hasn’t been an easy 31 years to be a fan.

Finally though the Chicago Cubs are getting it turned around, and I feel they have a very easy schedule this year compared to the sox. Let’s be honest folks, I am a major favorite here. Let me explain the wager.

One night my two neighbors and I were all playing an intense game of Yahtzee and having a few drinks. Jay who is a huge Chicago Whitesox fan had a little too much of the sauce and proposed a prop bet to me. The actual bet is very simple, whoever has a better record at the end of the season wins. I obviously take the cubs and he has taken the sox.

The loser has to camp out in the other guys back yard the first Friday and Saturday night after the MLB World Series. But here are the rules and where it gets good. Keep in mind the World Series is in October and in the Midwest it could be extremely cold or even worse, rainy.

1. The loser can only bring a standard size backpack and whatever is on their body.

2. The loser must stay in the others backyard for a minimum of 7 hours.

3. The loser may not hide or store any gear in the others backyard prior to the evening.

4. The loser can use any existing furniture, trees, or any pre existing equipment in the others backyard.

5. Weather or temperature is no excuse for not paying up on the bet.

So there you have it, this is the latest crazy prop bet I have got myself involved in. For the record, Jay is already trying to con me into spotting him 10 games. Ummmm, No.

So, as back-up (keeping in mind, sportswise I’m completely ignorant.. but just as a back up plan…) you could buy and install the neighbor a very nice hammock, or those comfy lean back patio chairs? Perhaps one of those misquito lamps, yknow next time you’re over there, just run home and grab one, due to the imaginary bug problem.

Invite yourself to a bbq, check out the facilities in advance … 7 hours over night..

I mean make sure a bar b, a cozy place to crash, and fill that pack up with something goodie to drink.. I didn’t read anywhere in your bet that you were required to sleep, or refrain from singing in drunken stupors and waking neighbors.

Hey LadyH, that all sounds great, BUT I am not planning on losing.

For him though, No I guess he doesn’t actually have to sleep.

I would expect some sort of webcam to be involved with this contest. Set it up to overlook the tent or better yet into the tent. Now that would be embarassing

Speaking of contests, any word on last months comment contest?

A webcam is a great idea! I think I can work that out. Ye I’m trying to figure out how to find all the comment post #’s from before I changed themes. Do you or Randy know who won? you were both close.

If nothing else I can split it up to both you.

I was at least 9 ahead when the names came off. The next day all the recent posts were still the ones from me from the day before so I am assuming that I did.

And yes a webcam would really rub it in.

Let me know what I need to do. I’ll probably be strolling over to your new forums also:)

Any word on this?

[...] in mind, Jay is the same die hard moron WhiteSox fan who made a prop bet with me earlier in the year on the Cubs vs. Sox overall record.  After this series I am confident [...]

[...] I made a great prop bet with my good friend and neighbor, Jay.  You can read all the details of the initial prop bet here.  The short version however is that we bet on the overall season record of the Chicago Whitesox [...]