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<!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>The Biggest Heartbreaks in Sports History</title><link rel="stylesheet" type="text/css" href="https://htlbid.com/v3/barstoolsports.com/htlbid.css"><script async src="https://htlbid.com/v3/barstoolsports.com/htlbid.js"></script><script async src="https://www.caffeine.tv/embed.js"></script><script>window.htlbid=window.htlbid||{},htlbid.cmd=htlbid.cmd||[],htlbid.cmd.push(function(){htlbid.setTargeting("pagetype","blog"),htlbid.setTargeting("brandId","63"),htlbid.setTargeting("authorId","14050"),htlbid.setTargeting("tags",["the-dog-walk","dog-walk","snake-draft","snake-drafts"]),htlbid.setTargeting("Verity_keywords",["number","frank","pick","world series","mugsy","one","guy","nate","boston red sox fan","chino","mikey bed","misery dana b.","tanky","first time","nice promo code"]),htlbid.setTargeting("Verity_IABv2",["521","545","507","492","483"]),htlbid.setTargeting("Verity_IABv3",["483","545","507","521","492"]),htlbid.setTargeting("Verity_positive","0.15"),htlbid.setTargeting("Verity_neutral","0.75"),htlbid.setTargeting("Verity_negative","0.1"),htlbid.setTargeting("Verity_GGT5_conf","HIGH"),htlbid.setTargeting("Verity_GGT5_risk","HIGH"),htlbid.setTargeting("Verity_GGT1_conf","VERY_HIGH"),htlbid.setTargeting("Verity_GGT1_risk","HIGH"),htlbid.setTargeting("is_testing","no"),htlbid.pubads().setPublisherProvidedId("PPID-GOES-HERE"),htlbid.layout()})</script><script src="https://d9rde3y35j061.cloudfront.net/script.js"></script><script src="https://htlbid.com/v3/barstoolsports.com/htlbid.js" async></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><script>window.htlAdUnitPath="57249056/in-app-iOS/Article-Page_In-Article-Unit",window.htlKeyvalues={authorId:"14050",category:"Chicago",tags:["the-dog-walk","dog-walk","snake-draft","snake-drafts"],brandName:"The Dog Walk",brandId:63,pagetype:"barstool_original"}</script></head><body class="union__content"><p>Frank, Dana and Nate enter the draft room for a Sports Heartbreaks Draft. We get into Frank's expert opinion on the topic, the biggest sports moments that haunt our lives forever, a questionable last round pick by Chief, and more.</p><p><a href="http://barstool.link/invitational" rel="noopener noreferrer" target="_blank"><img src="https://chumley.barstoolsports.com/union/2023/10/17/0Orag5YC.eb8049aa.jpg?fit=bounds&format=pjpg&auto=webp&quality=85%2C75" class="fr-fic fr-dib bs-image" draggable="true" alt data-image-provider data-image-author data-image-direct data-image-tracking data-image-id="hDXZDLQdWQP7i4xutxtXWiKL" srcset="https://chumley.barstoolsports.com/union/2023/10/17/0Orag5YC.eb8049aa.jpg?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=320 320w, https://chumley.barstoolsports.com/union/2023/10/17/0Orag5YC.eb8049aa.jpg?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=480 480w, https://chumley.barstoolsports.com/union/2023/10/17/0Orag5YC.eb8049aa.jpg?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=640 640w, https://chumley.barstoolsports.com/union/2023/10/17/0Orag5YC.eb8049aa.jpg?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=750 750w, https://chumley.barstoolsports.com/union/2023/10/17/0Orag5YC.eb8049aa.jpg?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=828 828w, https://chumley.barstoolsports.com/union/2023/10/17/0Orag5YC.eb8049aa.jpg?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=1080 1080w, https://chumley.barstoolsports.com/union/2023/10/17/0Orag5YC.eb8049aa.jpg?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=1200 1200w, https://chumley.barstoolsports.com/union/2023/10/17/0Orag5YC.eb8049aa.jpg?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=1920 1920w, https://chumley.barstoolsports.com/union/2023/10/17/0Orag5YC.eb8049aa.jpg?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=2048 2048w, https://chumley.barstoolsports.com/union/2023/10/17/0Orag5YC.eb8049aa.jpg?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=3840 3840w" sizes="(max-width: 1080px) 100vw, 776px" loading="eager" style="aspect-ratio:1.7777777777777777;width:100%"></a></p><p><strong><em>It's a college basketball event like no other. The 2023 Barstool Sports Invitational takes over Wintrust Arena in Chicago on Wednesday, Nov. 8. One night, two great games: Loyola Chicago vs. FAU at 6pm CT and Miss. State vs. Arizona State - 8pm CT. Get tickets now: </em></strong><a href="http://barstool.link/invitational" rel="noopener noreferrer" target="_blank"><strong><em>barstool.link/invitational</em></strong></a></p></body></html>

<p>Frank, Dana and Nate enter the draft room for a Sports Heartbreaks Draft. We get into Frank's expert opinion on the topic, the biggest sports moments that haunt our lives forever, a questionable last round pick by Chief, and more.</p><p><a href="http://barstool.link/invitational" rel="noopener noreferrer" target="_blank"><img src="https://chumley.barstoolsports.com/union/2023/10/17/0Orag5YC.eb8049aa.jpg?fit=bounds&format=pjpg&auto=webp&quality=85%2C75" class="fr-fic fr-dib bs-image" draggable="true" alt data-image-provider data-image-author data-image-direct data-image-tracking data-image-id="hDXZDLQdWQP7i4xutxtXWiKL" srcset="https://chumley.barstoolsports.com/union/2023/10/17/0Orag5YC.eb8049aa.jpg?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=320 320w, https://chumley.barstoolsports.com/union/2023/10/17/0Orag5YC.eb8049aa.jpg?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=480 480w, https://chumley.barstoolsports.com/union/2023/10/17/0Orag5YC.eb8049aa.jpg?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=640 640w, https://chumley.barstoolsports.com/union/2023/10/17/0Orag5YC.eb8049aa.jpg?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=750 750w, https://chumley.barstoolsports.com/union/2023/10/17/0Orag5YC.eb8049aa.jpg?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=828 828w, https://chumley.barstoolsports.com/union/2023/10/17/0Orag5YC.eb8049aa.jpg?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=1080 1080w, https://chumley.barstoolsports.com/union/2023/10/17/0Orag5YC.eb8049aa.jpg?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=1200 1200w, https://chumley.barstoolsports.com/union/2023/10/17/0Orag5YC.eb8049aa.jpg?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=1920 1920w, https://chumley.barstoolsports.com/union/2023/10/17/0Orag5YC.eb8049aa.jpg?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=2048 2048w, https://chumley.barstoolsports.com/union/2023/10/17/0Orag5YC.eb8049aa.jpg?fit=bounds&format=pjpg&auto=webp&quality=85%2C75&width=3840 3840w" sizes="(max-width: 1080px) 100vw, 776px" loading="eager" style="aspect-ratio:1.7777777777777777;width:100%"></a></p><p><strong><em>It's a college basketball event like no other. The 2023 Barstool Sports Invitational takes over Wintrust Arena in Chicago on Wednesday, Nov. 8. One night, two great games: Loyola Chicago vs. FAU at 6pm CT and Miss. State vs. Arizona State - 8pm CT. Get tickets now: </em></strong><a href="http://barstool.link/invitational" rel="noopener noreferrer" target="_blank"><strong><em>barstool.link/invitational</em></strong></a></p>

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The Biggest Heartbreaks in Sports History