The Misery of Losing in Fantasy Sports…

Where there are winners, there is a group of losers not far behind. The saying “if you’re not first, you’re last” is completely false. Breaking even is a win in my book. Hell, being down 100 bucks at the end of the week is still a win to me.

Fantasy football is all fun and games, until fantasy turns into reality. Normally that would be a good thing… but not for the last place finisher. Which in this case, was me. I was riding high off of my March Madness winnings from last year, and got cocky when it came to fantasy football.

We decided that the loser of our league must do a standup comedy routine… which I’m obviously hilarious, so that’s not a huge issue in this case. The fucked up part is that we had 2 punishments… the second one is something that will live forever and cause extreme embarrassment, considering I will be uploading the proof once I complete it. I MUST WEAR A DRESS THE BAR. Ok, there I said it. Judge me, troll me, you can even stalk me and kill me if you please, because honestly… anything beats wearing a dress in public. 

As a business man, I looked for every loophole possible… I felt like a lawyer who was trying to acquit his client of a murder charge, when there is distinctive video evidence of the crime. 

I schemed:

  • they never said I had to go inside 
  • I can wear a dress under my outfit!
  • I’ll buy a baby dress and slide it up my leg and put pants over it!
  • They never said the bar had to be open, so I’ll have my buddy open his bar when they’re closed and I’ll pop in and pop out. 

I went back to my roots, and one thing kept berating my mind. If you can’t do the time, don’t do the crime. I lost many nights of sleep over this, and it was all pointless. If you lose, you better do the punishment or else you are condemned by the Gambling God’s and never to hit a bet again. Also, everyone hates you and you’re blacklisted from the league and the friend group. I of course was gonna do it regardless, but a little boy can dream, can’t he?

Even with my incredible ability to get out of shit, I have no choice but to sack up and fully display my misery to celebrate everyone else’s successful fantasy season.

I will mention that our winner of the league, going into the final week decided to split winnings with 2nd place no matter the outcome. This was an embarrassing maneuver to make sure he had some winnings if he came in 2nd place (stupid, considering he won anyway). I submit that if the winner opts out of the winnings… then the loser can opt out of the losings. I still see this as a valid point, but I did the crime. I’m doing the damned time. I will wear my dress like the badge of dishonor that it is. At least I have the ovaries to do it… more than I can say for you renegers (google it if you must) out there. 

The short history I’ve had since losing has been quite the roller coaster ride. But my fellow leaguers have yet to realize the potential gold mine they are sitting on. They need to capitalize on my misery. Pictures, videos and stories are all fun and games. But while wearing a dress, it is important to capitalize in order to turn a punishment into being disciplined. A punishment is a one time thing, discipline lasts a lifetime. 

Only Rule: I can’t tell anyone at the bar I’m wearing a dress, as far as anyone is concerned… I’m just a man who loves wearing a dress.

I’m not sure what everyone else’s punishments (who’s reading this) look like.. but either way, there’s a set of rules to follow in order to capitalize on other’s misery.

(See how unbiased I am? I’m literally making a playbook for my friends to torture me, for your entertainment).

  1. Invite people outside of the league to witness the events. Leagues are intimate… break the barriers, and break your friends dignity.
  2. Footage is one thing, live streaming it for the world to see on Instagram and Facebook is another. Allow the people who weren’t invited to join the party 
  3. Make stricter rules off the bat. My league fucked up by leaving things too vague. We did not set an amount of time that last place has to wear the dress, so I will allow time for my misery to be exploited and go about my merry way.

Here is a Sports Center documentary on fantasy losers… skip through, or watch the whole video.

You can see that out of any of them… mine is 100% worse, and they are on national TV doing theirs. Even the dude dressed like a cowgirl got to do his in private (kind of). Was one of them getting his ankle waxed??? Not sure how that’s a big deal. That league clearly is filled with sober non-gamblers.

On that note, stay tuned for the evidence… enjoy my misery, and start brain storming on how humiliate our fellow Drunk Gamblers for decades to come!