Gambling! The ESPY's Are Tonight, and You Can Bet on Caitlyn Jenner's Cleavage

Imagine for a second that it's the summer of 1976. For those of you who were actually alive and self-aware in the summer of 1976, this exercise should be easy. If you weren't alive back then, use your imagination.  

So it's summer of 1976, and the Olympics are in Montreal. The Olympics, even back then (hell, ESPECIALLY back then), were a "star making" event. If you took home gold in a prominent Olympic event (or multiple prominent Olympic events — what's up, Mark Spitz?), you were set up for life. You were a national hero. In 1976, our new national hero was Bruce Jenner, who took home the gold medal in the decathlon . 

Thanks to the good folks at YouTube, let's go back in time and relive the magic….

So there you go… Bruce Jenner, quintessential man's man — gold medal, Wheaties box, patriotism, AMERICA! 

Now, imagine for a second that right after the Olympics, you were put into a Han Solo-style carbon freeze, sent into "perfect hibernation" for the next 39 years, and you woke up on July 15, 2015, and read the following sentence (on the screen of this laptop contraption, which by the way, blew your mind — a computer on my LAP?!?):

Tonight, you can place bets online as to whether or not Caitlyn Jenner (the transgender woman, formerly Bruce Jenner) will be showing cleavage when she makes her speech at the ESPY Awards, a creation of all-sports network ESPN, tonight.

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Think about how much is going on in that one sentence — you went to bed 39 years ago, woke up, and now there's an internet, an all-sports channel, an awards show in which that all-sports channel masturbates about itself recognizes the best of the best in the sports world, the ability to gamble from your house (hell, from your phone), and the ability to gamble on cleavage. 

Oh, and Bruce Jenner is now a woman. (A woman with tremendous boobs, I might add.) There's that. 

I believe this is what a paroled Brooks Hatlen meant in Shawshank Redemption when he lamented that "the world went and got itself in a big damn hurry." (And we all know what happened to Brooks right after that. #RIPBrooks #BrooksWasHere) Bruce Jenner is now Caitlyn Jenner, and we live in an age where we will literally gamble on anything, so why not gamble on the ESPY's tonight, and why not gamble on Caitlyn's freshly minted cleavage? 

Yes, in 2015, these are all activities that are readily available. The ESPY's are on tonight, and as much as I bag on ESPN, I will admit that a) I watch the ESPY's and b) the show is always good for a few memorable (for the right reasons) moments. Now, this year's show is probably the most controversial ESPY's that we've experienced, due wholly to Jenner receiving the Arthur Ashe Courage Award in the wake of her transition to life as a woman. It's a very polarizing topic.

Honestly, I hope that the ability to gamble on it will bridge some of these societal gaps. I mean, that's what gambling does!  Sit at a good blackjack table for a night and tell me that it's not a beautiful melting pot where you love your neighbor almost unconditionally (as long as they're not splitting face cards). You can't!

So without further ado, here are the odds on not just Caitlyn Jenner, but also the most high profile of the ESPY's that will be handed out tonight:

Caitlyn Jenner Cries during Acceptance Speech
Yes +120
No -150
PREDICTION: YES +120. I would imagine that this will be a pretty overwhelming moment for Caitlyn, and even though it's an award for courage (which inherently would seem to mean crying is off limits), YES as the underdog is good value. 

Caitlyn Jenner to Show Cleavage
Yes -260
No +200
PREDICTION: YES -260. Even at =260, this would seem to be the best value on the board. I feel like we have yet to see a Caitlyn Jenner public appearance where she hasn't shown her cleavage. And rightfully so! She should be proud of those puppies!

Caitlyn Jenner's Speech Time
Over 4 Minutes & 51 Seconds -120
Under 4 Minutes & 51 Seconds -110
PREDICTION: UNDER -110. There are plenty of adjectives to describe Caitlyn Jenner. "Talkative" doesn't appear to be one of them, although admittedly I'm basing like 95 percent of this assessment on Keeping Up With The Kardashians, where that whack job crew routinely puts Caitlyn in a corner…..

Caitlyn Jenner's to Mention Kim or Kanye in Speech
Yes +150
No -185
PREDICTION: NO -185. ….and this is the moment Jenner comes out of the corner. Tonight is a Kardashian-free zone. 

Color of Caitlyn Jenner's Dress(Arthur Ashe Award)
Gold/Silver +300
Blue/Purple +350
Green/Turquoise +700
Black +225
White +400
Red/Maroon +350
Yellow/Orange +700
PREDICTION: WHITE +400. Not sure why black is such a heavy favorite. This isn't a funeral! I'll go with white, based on Caitlyn likely wanting to show off her spray tan. White accentuates that. 

Best Female Athlete
Serena Williams (Tennis) -225
Ronda Rousey (MMA) +165
Lindsey Vonn (Skiing) +3300
Breanna Stewart (uConn) +5000
PREDICTION: WILLIAMS -225. Second best "favorite" value on the board behind Caitlyn's cleavage. 

Best Fighter
Floyd Mayweather Jr (Boxing) -185
Ronda Rousey (MMA) +135
Donald Cerrone (MMA) +2000
Terence Crawford (Boxing) +2000
Gennady Golovkin (Boxing) +2000
PREDICTION: MAYWEATHER -185. And admittedly, I'd like to see Rousey come up on stage and interrupt the acceptance speech, and slap Mayweather in an arm bar. 

Best Game
Seattle vs New England (Super Bowl) -1500
Oakland vs Kansas City (AL Wild Card) +1000
San Antonio vs LA Clippers G7 (NBA) +1000
PREDICTION: SEA vs NE -1500. Pretty lackluster year for this category when there are only three finalists and two of them are from playoff rounds that are before the conference finals/league championship series.

Best Male Athlete
Stephen Curry (Golden State) -500
LeBron James (Cleveland) +375
Aaron Rodgers (Green Bay) +425
JJ Watt (Houston) +1000
PREDICTION: JAMES +375. If Curry is -500, then someone knows something and he's probably winning, but in my heart of hearts, I feel like the right way to do this is to give the Male Athlete award to James, an off the charts, alien freak of an athlete, and give…..

Best NBA Player
LeBron James (Cleveland) -155
Stephen Curry (Golden State) +110
James Harden (Houston) +2000
Russell Westbrook (Oklahoma City) +2000
Anthony Davis (New Orleans) +3300
PREDICTION: CURRY +110. ….to Curry, who was the best basketball player on the planet for a big chunk of the last year (while LeBron was ramping up in Cleveland), and valuable enough to win the MVP award.

Best NFL Player
JJ Watt (Houston) -500
Aaron Rodgers (Green Bay) +300
Tom Brady (New England) +1000
DeMarco Murray (Dallas) +6600
Antonio Brown (Pittsburgh) +8000
PREDICTION: WATT -500. This will give us a reason to discuss J.J. on Thursday, keeping the streak alive for "days talking about J.J. Watt."

Enjoy the ESPY's, people! 

Listen to Sean Pendergast on SportsRadio 610 from 2 p.m. to 7 p.m. weekdays. Also, follow him on Twitter at

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