Caitlyn Jenner Prop Bets for the ESPYs

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They say you can bet on just about anything these days…especially offshore. This Wednesday night is the annual celebration of Excellent Sports Performance Yearly (ESPY) awards, but the show itself won’t be what catches headlines this year.  Instead, a former Olympic gold medal decathlete will occupy the spotlight and one offshore sportsbook ( is taking the opportunity to let bettors bet on a few novelty propositions.

Before you feign outrage at any potential insensitivity shown by these props, understand the job of an oddsmaker is to be creative with his craft, forcing gamblers of all ability levels to make tough wagering decisions before investing. Having reviewed this particular list below, making money will definitely be a challenge without proper intel.  

Let’s start with the first impression a woman will make at any awards show.

Caitlyn Jenner’s dress color

Gold/Silver  +250

White  +500

Black  +450

Blue/Purple +300

Red/Maroon  +500

Yellow/orange  +650

Green/turquoise +450

This is for all you fashionistas out there to dissect.  I won’t even venture an opinion on a decision-making process known to create endless stress for women. According to this article from the Daily Mail, women spend five months of their working lives picking outfits: an average of 90 minutes a week choosing what to wear. If this is the case just for heading to the office, there’s zero chance I’m handicapping a woman’s choice in formal attire for an appearance of this magnitude.

Caitlyn Jenner speech time 

Over/Under 4 minutes and 51 seconds

If you’re handicapping this prop it’s more about historical perspective and previous speeches than the message itself.  I’ve probably watched the ESPY’s once in their entirety so this is a bet I’m ill-equipped for unless I go all PCU tonight trying to watch every previous speech in ESPY award show history.

Caitlyn’s speech: Kim or Kanye mentioned

Yes +140

No -180

If Caitlyn mentions either of these idiots it will surely take away from the courageous life choice she made.  I’d find it hard to believe she was inspired by either of them. Give me No for every penny of the Travis fortune.

Caitlyn Jenner cries during speech

Note: Will Kaitlyn Jenner cry during her Arthur Ashe acceptance speech. No speech = no action.

Yes +120

No -160

I like the stipulation that there’s no action without an actual speech leading me to the YES here at +120.  We’ve seen in the past the Arthur Ashe award elicits strong emotions not only in the audience but also from the individual accepting the award. I’ll make the case the dog price is live.

Will Caitlyn Jenner show cleavage?

Yes -260

No +200

This is the easiest bet of all if you ask me… betting yes that Caitlyn Jenner will show cleavage in her formal attire.  Keep in mind betonline paid both the yes and no on “Will Katy Perry show cleavage during the Superbowl?” meaning that they’ve established precedent for awarding a win on both sides if there’s a grey area.  Call me a traditionalist but I really believe Ms. Jenner won’t show up to the ESPY’s all buttoned up for an evening of pageantry in LA.

There you have it…a complete handicap of ESPY props involving Caitlyn Jenner.  Grab your friends and colleagues; there’s always a dollar to be made when award shows take center stage.  Meanwhile I’ll go back to figuring out what SEC football team will be this year’s edition of 2014 Texas A&M.

Written by Clay Travis

Clay Travis is the founder of the fastest growing national multimedia platform, OutKick, that produces and distributes engaging content across sports and pop culture to millions of fans across the country. OutKick was created by Travis in 2011 and sold to the Fox Corporation in 2021.

One of the most electrifying and outspoken personalities in the industry, Travis hosts OutKick The Show where he provides his unfiltered opinion on the most compelling headlines throughout sports, culture, and politics. He also makes regular appearances on FOX News Media as a contributor providing analysis on a variety of subjects ranging from sports news to the cultural landscape. Throughout the college football season, Travis is on Big Noon Kickoff for Fox Sports breaking down the game and the latest storylines.

Additionally, Travis serves as a co-host of The Clay Travis and Buck Sexton Show, a three-hour conservative radio talk program syndicated across Premiere Networks radio stations nationwide.

Previously, he launched OutKick The Coverage on Fox Sports Radio that included interviews and listener interactions and was on Fox Sports Bet for four years. Additionally, Travis started an iHeartRadio Original Podcast called Wins & Losses that featured in-depth conversations with the biggest names in sports.

Travis is a graduate of George Washington University as well as Vanderbilt Law School. Based in Nashville, he is the author of Dixieland Delight, On Rocky Top, and Republicans Buy Sneakers Too.