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.

I often wonder what it feels like to be a prisoner on death row with a few months left to go. Although I am not days away from being executed, I am a couple months away from losing my hair. Some of you may remember before the NFL season started that I made a bet with my neighbor. The bet was that the Chicago Bears would finish this season with a better record than the Packers.

At the time this seemed like a great prop. After all, the Packers sucked last year, and the Bears almost won the Superbowl. Plus it would have been great seeing my neighbor fly a gay flag in his front yard for a seven days. Well, here we are after week 15 and my loss is imminent. Initially I was just going to get it over with and shave my head this weekend. After further review however I am going to wait until Superbowl Sunday. What a great way to end a dismal season eh…..<——-(not Canadian)

I blame losing this bet solely on the Chicago Bears offensive coordinator Ron Turner. I don’t even think he could coach the local community college to a winning season, let alone an NFL team. His play selections are horrible. Mr. Turner, if for some reason you ever come across this post while searching your name in google, please click here immediately. Although considering my bet, I will be waiting for you when you get there.

My wife was not to thrilled about the prospect of me showing up at Christmas gatherings this year looking like a skin head. And actually now that I think about it, I am probably going to be speaking at CAP Euro, so I mine as well wait.

Note to self, no more proposition betting pre-season while intoxicated. Have a great weekend!

And prepare for a potential BIG ANNOUNCEMENT on this blog next week………….Oh the suspense.

As many of you know I love proposition bets. I love gambling with friends, but I hate taking money from them. Let’s be honest, if I take $20 from a buddy or he takes it from me, what difference does it really make.

So on Friday night my good friend and neighbor Jay said he could beat me in a 100 yard dash. Keep in mind I have ran 2 marathons with my best time being under 3:30. When I was in my best shape, I could run a mile in less than 4:40. So of course I was up for the challenge. We set the the time for the race at 11:30 on Saturday morning.

Jay is a pretty athletic guy and plays softball, basketball, and hockey. Nonetheless, I will destroy him when it comes to running any type of distance, including a 100 yard dash.

So I went to bed early on Friday night after having a nice relaxing night watching the movie Hostel with my wife. <——- craziest movie I have ever seen. I live on the coolest street in the world and my neighbors have become some of my very closest friends. (and if Karl is reading this, you need to move here……baller) But anyhow Saturday morning came and as expected Jay was late and no where to be found. My other neighbor John and I went and got him out of the house around 12:30.

Now mind you, my in-laws were over and we had a crowd of neighbors and kids that had to be at least 15-20 people waiting to watch this much anticipated race.

The bet was this; Whoever lost has to go to the bar to watch the Packer / Cowboys game on Thursday Nov. 29th wearing Greenbay gear and buy drinks all night. We are both huge Bears fans and absolutely despise the Packers. Our gay friend and neighbor John is a Packer fan however.

So finally Jay comes out and we have the typical stare down before the race……please notice the Carl Lewis spandex I have on. (warm up gear)

So in front of all the fans, we have the girls run the finish line tape across the street and the race is ready to go. Well all of the sudden Jay wants to shorten the course from one mailbox to another. Hell, this “new distance” has to be only 40 yards at best. Obviously somewhere around the distance from home plate to first. Easily in Jay’s favor being a softball player. When he came outside he had a beer and a bag of cookies, so I knew I had a huge edge right from the start.  So being the good friend and realizing he was struggling I said O.K.

Well John fired off the gun and the race was off. Needless to say, I killed him by a nice margin. BUT, of course while I was oxygen deprived right after the race and not thinking straight, Jay said let’s do best out of 3. Keep in mind I am a distance runner and not a sprinter, my legs were shot. Worst gambling decision I ever made, I could have just walked away and taken the win, but because I felt sorry for the guy I said fine 2 out of 3.

Well, I ended up getting beat the next 2 races by less than a nose, and lost the bet. I was pretty pissed all day about it. That was like turning $100 into $4000 playing poker and then losing it all. I was so stupid to not even get any odds or a new bet after winning the first race, but whatever. Actually I was stupid for even agreeing to do best out of 3 after winning the initial race. My legs were done after the first race.

So the bottom line is I got hustled by Jay.

Now, what do I do from here. Of course I will honor the bet and wear the shitty Green Bay gear at the bar as well buy the drinks. But I think Jay forgot who is messing with. My office IS the internet, and although I have to buy drinks and wear a Packer shirt, I would still like to own him. So I did just that.

Jay is in our fantasy league and his team “Green Weiner’s” is absolutely terrible. So from here on out I now own Jay Sandine…….literally

I lost a bet due to my own stupidity, but for the rest of his life I will own Jay. (I could have done a lot worse, but Jay has a high profile job in the community and I had to be somewhat reserved)

JaySandine.com

This blog seems to be all business lately. So let’s have some fun. Before you go any further, check out this crazy bitch. It just seemed like the right thing to post since I also have a gay flag on this page.

Anywho, on to more important stuff. As many of you know I love to gamble. Although gambling on poker, sports, or casino games can be fun, I personally get a lot more satisfaction doing proposition bets. In fact I’ll share my latest prop bet.

My good friend and neighbor John (the big dude in the middle) is such a die hard Green Bay Packer fan that this dumb ass made the following bet. If Green Bay has a better overall record than the reigning NFC Champion Chicago Bears, then he will have the pleasure of shaving my head with a dull razor. Damn, that could be cold this winter!

But here is the best part, If when the Bears finish up the season with a better record he will have to fly a gay flag outside his home for 1 week. Note to fellow gamblers……..Bet with your head and not your heart.

Okay, as you can see I have a lot of fun messing with friends and doing crazy proposition bets. Below however are my favorite proposition bets. These are great bets to make at bars with drunk buddies for either free drinks or cold hard cash.

If you use any of these in coming weeks and make a profit, please ship the customary 10% to me via paypal. Alright, here goes in order of my favorite:

1. The Circumference of a Beer Glass - This is a classic and you will win this all day long. (Don’t lie, you know you just went into your kitchen to grab a glass and try it out.)

2. 6 Saltines in a Minute Challenge - Okay this one is good. Eating 6 saltine crackers in a minute doesn’t sound that difficult, but believe me it is. I have only seen one person do this successfully. The problem is that saltines literally dry up all the saliva in your mouth and you are unable to swallow. When making this bet, you cannot allow the suspect to drink any water or liquids during the 60 second period. (Gay Video, but I didn’t have time to scour Youtube for a better one)

3. Break a Beer Bottle With Your Bare Hands - This is also a good one but can be quite messy. It really only works well at house parties or if you have a sink to do it over. Definitely not the most profitable prop bet, but it does work.

4. Open a Beer Bottle With A Piece of Paper - Again, not as great as #’s 1 & 2, but it will trick most people. Good luck finding a sheet of 8×10 paper at the bar.

I actually have many more, but these are my favorites. If you have some good ones, please post in the comments. The first one I have actually found to work the best. Happy Gambling!