<!DOCTYPE html><html lang="en"><head><meta charset="utf-8"><meta name="viewport" content="width=device-width,initial-scale=1,maximum-scale=1,user-scalable=no,shrink-to-fit=no"><title>Jason Whitlock's Guess That Ass</title><link rel="stylesheet" type="text/css" href="https://htlbid.com/v3/app.barstoolsports.com/htlbid.css"><script async src="https://htlbid.com/v3/app.barstoolsports.com/htlbid.js"></script><script>window.htlbid=window.htlbid||{},htlbid.cmd=htlbid.cmd||[],htlbid.cmd.push((function(){htlbid.setTargeting("pagetype","blog"),htlbid.setTargeting("authorId","44"),htlbid.setTargeting("Verity_keywords",["jason whitlock","guess","ass | barstool sports","hats","beanies","flag","hoodies","big game | new football t-shirts","more shop","gear","freeteanna","one"]),htlbid.setTargeting("Verity_IABv1",["IAB17","IAB17-12"]),htlbid.setTargeting("Verity_IABv2",["484","483"]),htlbid.setTargeting("Verity_IABv3",["484","483"]),htlbid.setTargeting("Verity_neutral","1"),htlbid.setTargeting("Verity_GGT5_conf","HIGH"),htlbid.setTargeting("Verity_GGT5_risk","MEDIUM"),htlbid.setTargeting("Verity_GGT4_conf","VERY_HIGH"),htlbid.setTargeting("Verity_GGT4_risk","HIGH"),htlbid.setTargeting("is_testing","no"),htlbid.layout()}))</script><script>var googletag = googletag || {};
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        pbjs.setConfig({ pageUrl: https://www.barstoolsports.com/blog/559023/jason-whitlocks-guess-that-ass });</script><script src="https://d9rde3y35j061.cloudfront.net/script.js"></script><script src="https://iframely.barstoolsports.com/embed.js" async></script><style>.union__content{font-family:-apple-system,HelveticaNeue,Roboto,sans-serif;font-weight:400;font-size:18px;color:#5a5b5d;word-wrap:break-word;box-sizing:border-box;padding:0 5px 32px 5px}.union__content p{padding:0;margin:16px 0 0 0}.union__content img{display:block;width:100%!important;height:auto;margin:16px 0 0 0}.union__content video{display:block!important;width:100%!important;height:auto;margin:16px 0 0 0}.union__content .articleAd{text-align:center;margin:16px 0 0 0;background-color:#f5f5f5}.union__content .htlad__container{display:inline-block}.union__content p a{color:#377dc4}.union__content .oembed__wrapper{margin:16px 0 0 0}.union__content blockquote:not(.twitter-video){display:block;margin:16px 0 0 0;padding:4px 12px;border-left:4px solid #77889a;font-style:italic;background:#f0f4f8;text-align:left;border-radius:0 6px 6px 0}.union__content blockquote:not(.twitter-video) p{font-style:italic}.union__content blockquote,q{quotes:none}.union__content iframe{max-width:100%}.union__content .bs-image-hidden{display:none}.union__content div.hq-image{width:fit-content;margin:0 auto}.union__content span.image-attribution,.union__content span.image-attribution a{color:#757575;font-size:12px;font-style:italic;letter-spacing:.1px;line-height:14px;text-decoration:none;padding:0;margin:0}.union__content .bs-videoPlayer .bs-videoPlayer__container,.union__content video-js,.wp-video{width:100%!important;height:0!important;position:relative;padding-bottom:56.25%;overflow:hidden;margin:16px 0 0 0}.wp-video video{width:100%!important;height:100%!important}.hq-image video{width:100%!important;height:100%!important}.union__content .bs-videoPlayer__container>iframe{position:absolute;top:0;left:0;width:100%;height:100%;border:none}@media (prefers-color-scheme:dark){.union__content,body,html{background:#1c1c1c;color:#f1f1f1}.union__content blockquote:not(.twitter-video){border-left:4px solid #367dc4;background:#272c35}}</style><script>window.addEventListener("applicationDidBecomeActive",(()=>{document.querySelectorAll(".hq-image video[autoplay]").forEach((e=>e.play()))}))</script></head><body class="union__content"><p><a href="https://cdn.barstoolsports.com/wp-content/uploads/2016/06/02/Screen-Shot-2016-06-02-at-11.55.50-AM.png"><img class="alignnone size-full wp-image-559024" src="https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75" alt="Screen Shot 2016-06-02 at 11.55.50 AM" width="1058" height="754" srcset="https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=320 320w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=480 480w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=640 640w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=750 750w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=828 828w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=1080 1080w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=1200 1200w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=1920 1920w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=2048 2048w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=3840 3840w" sizes="(max-width: 1080px) 100vw, 388px" loading="eager" style="aspect-ratio:1.7244444444444444"></a></p><p> </p><p>Hey Whitlock! This one’s for you!</p><p>#FreeTeanna</p><p><a href="https://cdn.barstoolsports.com/wp-content/uploads/2016/06/02/Screen-Shot-2016-06-02-at-11.57.42-AM.png"><img class="alignnone size-full wp-image-559026" src="https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75" alt="Screen Shot 2016-06-02 at 11.57.42 AM" width="1066" height="1118" srcset="https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=320 320w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=480 480w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=640 640w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=750 750w, 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href="https://cdn.barstoolsports.com/wp-content/uploads/2016/06/02/Screen-Shot-2016-06-02-at-11.57.54-AM.png"><img class="alignnone size-full wp-image-559027" src="https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75" alt="Screen Shot 2016-06-02 at 11.57.54 AM" width="1190" height="1162" srcset="https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=320 320w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=480 480w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=640 640w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=750 750w, 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href="https://cdn.barstoolsports.com/wp-content/uploads/2016/06/02/Screen-Shot-2016-06-02-at-11.58.08-AM.png"><img class="alignnone size-full wp-image-559028" src="https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75" alt="Screen Shot 2016-06-02 at 11.58.08 AM" width="964" height="1126" srcset="https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=320 320w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=480 480w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=640 640w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=750 750w, 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href="https://cdn.barstoolsports.com/wp-content/uploads/2016/06/02/Screen-Shot-2016-06-02-at-11.59.08-AM.png"><img class="alignnone size-full wp-image-559032" src="https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75" alt="Screen Shot 2016-06-02 at 11.59.08 AM" width="1188" height="1192" srcset="https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=320 320w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=480 480w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=640 640w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=750 750w, 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<p><a href="https://cdn.barstoolsports.com/wp-content/uploads/2016/06/02/Screen-Shot-2016-06-02-at-11.55.50-AM.png"><img class="alignnone size-full wp-image-559024" src="https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75" alt="Screen Shot 2016-06-02 at 11.55.50 AM" width="1058" height="754" srcset="https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=320 320w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=480 480w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=640 640w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=750 750w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=828 828w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=1080 1080w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=1200 1200w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=1920 1920w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=2048 2048w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=3840 3840w" sizes="(max-width: 1080px) 100vw, 388px" loading="eager" style="aspect-ratio:1.7244444444444444"></a></p><p> </p><p>Hey Whitlock! This one’s for you!</p><p>#FreeTeanna</p><p><a href="https://cdn.barstoolsports.com/wp-content/uploads/2016/06/02/Screen-Shot-2016-06-02-at-11.57.42-AM.png"><img class="alignnone size-full wp-image-559026" src="https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75" alt="Screen Shot 2016-06-02 at 11.57.42 AM" width="1066" height="1118" srcset="https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=320 320w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=480 480w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=640 640w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=750 750w, 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https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=828 828w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=1080 1080w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=1200 1200w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=1920 1920w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=2048 2048w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=3840 3840w" sizes="(max-width: 1080px) 100vw, 388px" loading="lazy" style="aspect-ratio:1.7244444444444444"></a><a href="https://cdn.barstoolsports.com/wp-content/uploads/2016/06/02/Screen-Shot-2016-06-02-at-11.59.08-AM.png"><img class="alignnone size-full wp-image-559032" src="https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75" alt="Screen Shot 2016-06-02 at 11.59.08 AM" width="1188" height="1192" srcset="https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=320 320w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=480 480w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=640 640w, https://chumley.barstoolsports.com/union/2025/07/25/Img-Not-Avail.50164f2b.png?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=750 750w, 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