Over the past few years, not many prop bets have gone exceptionally well for me.  If you can remember back to 2007, I had to shave my head bald on Superbowl Sunday due to the Green Bay Packers having a better season record than the Chicago Bears.

This past baseball season however 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 versus the Chicago Cubs.  The loser would have to spend the night in the winners backyard the first weekend after the world series.

Obviously Jay lost the bet, and this weekend was time for him to make good on it.  Luckily for Jay, the weather was unseasonably warmer than normal this weekend for the first week in November.  Nonetheless the temperature did climb down to around 40 degrees during the middle of the night.

Jay is a pretty clever dude though.  The rules of our bet stated that the loser could only bring with them a college sized backpack, and whatever could fit on their body.  As you can see in the pictures below, Jay showed up with 1 bag and several layers on.

He then began to set up his camp site in the wooded area in my backyard.  And then it all began………..

About a half hour after Jay arrived, people started arriving with beer, chicken wings, steaks, firepits, firewood, tents, portable electronics, etc.  Needless to say, Jay planned and executed one heck of a party that evening in my backyard.  I have to say I was impressed at Jay’s ability to turn a positive into a negative.

Overall it was a fun night.  I think everyone left and called it a night around 2:00 A.M., at which point Jay was left to sleep by himself in my backyard.  Judging by his demeanor the following morning, I have to assume that he did not have a lot of fun.  Even being in a tent, I can’t imagine a 40 degree night on the wet ground, all by yourself, in your neighbors backyard would be a lot of fun for anyone.

Here are the pictures below.  I guess it’s about time to find another crazy prop bet to get involved in.

Jay’s Arrival

The Set-up

The Equipment

Looks Comfortable To Me – NOT

Ever Slept In A Hammock For 7 Hours?

And The First Guests Start Arriving

Good Thing I Left The Grill In The Backyard

Lucky Jay, One Of His Guest Brought Him A Tent

Overall, I give jay a 10 on cleverness and planning.  Nice work, next year the rules will be written in much finer detail.

That is classic. I give Jay a lot of credit for making good on his bet. He is a pretty clever guy, I’m just wondering where my invite was!

I’m surprised he didn’t sneak a drum and start banging on it all night outside your window to keep you from sleeping.

Much simpler and more easily executed plan than having a party. Either way, sounds like he was able to twist things slightly back towards his favor, thanks for sharing!

That is too funny. You guys make some hilarious bets.

Actually I was one step ahead of him. I had a speaker that was going to loop “Go Cubs Go” the entire night. But then I decided to be a nice guy at the end of the night and let him off the hook.

I think your neighbor is cute!

Man this sort of thing makes me miss my friends back in the Midwest. I mean don’t get me wrong, I have slept in someones back yard before! This is a JE.com classic!