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 entry was posted on Sunday, November 4th, 2007 at 9:33 pm and is filed under Prop Bets. You can follow any responses to this entry through the RSS 2.0 feed. You can skip to the end and leave a response. Pinging is currently not allowed.