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</div><div class="page-header article-page-header"><div class="background-highlight"></div><div class="content"><div class="container"><div class="heading-container"><h1 class="page-title">The 10 Biggest Bets In March Madness History</h1></div><div class="header-background-image"><picture class="picture"><source srcSet="https://imagedelivery.net/hoXdcCyL8VZtxGv-T1axXw/a099362e-02db-4312-4b88-0a83891f1800/public"/><img class="image" src="https://imagedelivery.net/hoXdcCyL8VZtxGv-T1axXw/a099362e-02db-4312-4b88-0a83891f1800/public" alt="The 10 Biggest Bets In March Madness History-picture"/></picture></div><div class="article-image"><picture class="picture"><source srcSet="https://imagedelivery.net/hoXdcCyL8VZtxGv-T1axXw/9aef4c8b-d4f7-46f1-4e4e-239e08473400/public"/><img class="image" src="https://imagedelivery.net/hoXdcCyL8VZtxGv-T1axXw/9aef4c8b-d4f7-46f1-4e4e-239e08473400/public" alt="The 10 Biggest Bets In March Madness History-picture"/></picture></div></div></div></div><div class="container article-content-container"><div class="author-date">Mar 24, 2023<!-- --> <!-- --> • <!-- --> <!-- -->PickBoss</div><div class="article-content"><p> </p><p>There are some great sporting events that take place each year, but few are more significant than the NCAA Tournament. March Madness has been popular for decades, but that popularity has only seemed to get bigger with the expansion of legal sports betting. </p><p> </p><p>While most bettors tend to make small bets during the NCAA Tournament, that is different from how some bettors go about it. There are some huge sports bettors out there, and they are looking to win big during March. </p><div class="raw-html-embed"><center><div class="metabet-gametile metabet-size-728x90 metabet-query-534457"></div></center></div><div class="raw-html-embed"><center><div class="metabet-gametile metabet-size-728x90 metabet-query-534464"></div></center></div><div class="raw-html-embed"><center><div class="metabet-gametile metabet-size-728x90 metabet-query-534458"></div></center></div><div class="raw-html-embed"><center><div class="metabet-gametile metabet-size-728x90 metabet-query-534474"></div></center></div><h2><br>Biggest Bets in March Madness History</h2><p>Most of the biggest bets ever made on March Madness are going to be <a href="https://www.pickboss.com/march-madness-parlay-betting">futures betting</a>, but there has been some big parlay hits as well. Here are 10 of the biggest bets and biggest wins during March Madness. </p><p></p><h2>1. Florida -8 vs. Oral Roberts</h2><p> </p><p>Most bettors tend to win big when betting on an underdog team, but that wasn’t the strategy used by one bettor a few years ago. After Oral Roberts pulled off a stunning upset over Ohio State as a 15-seed, one bettor decided to fade them in the next round. </p><p> </p><p>A bettor decided to make a $224,000 bet on the Gators to win and cover the eight-point spread. The reward would have been $204,000, and this bet was looking good in the first half, but things turned quickly. </p><p> </p><p>Not only did Florida end up failing to cover the spread, but Oral Roberts won the game and advanced all the way to the Sweet 16. </p><p> </p><h2>2. Tar Heels Come Up Short</h2><p> </p><p>Making a futures wager is a great way to win big, but you also take on a ton of risk. One bettor found out the hard way in 2019 as picking the favored North Carolina Tar Heels ended up being a significant loss of money. </p><p> </p><p>Before the NCAA Tournament started in 2019, William Hill Sportsbook took on a $10,000 bet on the Tar Heels to cut down the nets. That would have paid out $80,000 and would have been a massive payday. </p><p> </p><p>That bet ended early, though, as the Tar Heels failed even to reach the Final Four. </p><p> </p><h2>3. “Mattress Mack” in Action</h2><p> </p><p>Jim McIngvale is known as “Mattress Mack” due to his furniture store that he has in Texas, and he is also one of the biggest sports bettors in the country. Mattress Mack loves to make futures wagers, and you will struggle to find anyone that has the type of cash that he does. </p><p> </p><p>During the 2021 NCAA Tournament, Mattress Mack decided to place a $1 million wager on the Houston Cougars to win the title. That bet would have paid out $9 million, but ultimately the Cougars were defeated by the Baylor Bears in the Final Four. </p><p> </p><h2>4. Ohio State Ruins Big Bet</h2><p> </p><p>After a runner-up finish in the 2021 Big Ten Tournament, the Ohio State Buckeyes were a trendy pick to make a deep run in the NCAA Tournament. They were getting so much attention that one bettor decided to wager $100,000 on them to win the National Championship. </p><p> </p><p>If the Buckeyes were able to cut down the nets and win the title, it would have resulted in a multi-million dollar win for the bettor at William Hill Sportsbook. That bettor didn’t have to sweat out his bet long, though, as the Buckeyes lost in the first round, and William Hill was able to benefit from the poor bet. </p><p> </p><h2>5. Futures Parlay Goes to Waste</h2><p> </p><p>Futures betting is usually a way to go if you want a big win, but coming to some future bets into a parlay can result in a massive payday. That was the strategy used by one bettor that looked to pick the eventual national champion. </p><p> </p><p>A bettor placed a combination future wager on four different college basketball programs, and just one of them had to win the national championship. This $100,000 bet included Duke, Gonzaga, Michigan, and Kansas, and all four teams were in the top-15 betting favorites. </p><p> </p><p>Unfortunately, none of those teams ended up even making the Final Four, and that bet was over before the final weekend. That was an interesting wager to make, but ultimately it resulted in a donation of $100,000. </p><p> </p><p> <div class='video-grid'> <div class="video-thumbnail solo" id='article-video-player' data-video-title='March Madness Contender - Kansas' data-video-src='{"videoId":"76fa6f82-393f-4239-8b52-5b7d51518f98"}' > <div class="video-thumbnail-image"> <picture class="picture"> <img class="image" alt={alt ?? ""} sizes= (min-width: 394px) 346px calc(100vw - 48px) src=https://imagedelivery.net/hoXdcCyL8VZtxGv-T1axXw/c339b9e3-c375-41d1-84d4-0e9ace27b100/w=346,fit=contain srcSet=https://imagedelivery.net/hoXdcCyL8VZtxGv-T1axXw/c339b9e3-c375-41d1-84d4-0e9ace27b100/w=272,fit=contain 272w,https://imagedelivery.net/hoXdcCyL8VZtxGv-T1axXw/c339b9e3-c375-41d1-84d4-0e9ace27b100/w=327,fit=contain 327w,https://imagedelivery.net/hoXdcCyL8VZtxGv-T1axXw/c339b9e3-c375-41d1-84d4-0e9ace27b100/w=346,fit=contain 346w,https://imagedelivery.net/hoXdcCyL8VZtxGv-T1axXw/c339b9e3-c375-41d1-84d4-0e9ace27b100/w=544,fit=contain 544w,https://imagedelivery.net/hoXdcCyL8VZtxGv-T1axXw/c339b9e3-c375-41d1-84d4-0e9ace27b100/w=654,fit=contain 654w,https://imagedelivery.net/hoXdcCyL8VZtxGv-T1axXw/c339b9e3-c375-41d1-84d4-0e9ace27b100/w=692,fit=contain 692w /> </picture> </div> <div class="tag">Basketball</div> <div class="title-container"> <h2 class="video-title">March Madness Contender - Kansas</h2> </div> </div> </div> </p><p> </p><h2>6. A Chance at $47 Billion</h2><p> </p><p>You would think that in order to win $47 billion potentially, it would take a pretty massive wager. That wasn’t the case during the 2021 NCAA Tournament as one bettor had a chance to win that much money with a wager of just $0.10. </p><p> </p><p>This was obviously a massive longshot bet, as the bettor included six huge underdogs in a six-leg moneyline parlay. There wasn’t a real threat of this bet ever hitting, but it was an impressive attempt at a chance to cash in with only six legs and a tiny stake. </p><p> </p><h2>7. Mattress Mack Cashes In</h2><p> </p><p>Mattress Mack is back on this list, but this time his bet wasn’t a futures bet at all. In fact, this bet was almost made out of desperation as Mattress Mack was potentially on the hook to lose millions at his furniture store in Texas. </p><p> </p><p>Last April, McIngvale had to take a helicopter ride to Louisiana in order to place two wagers worth up to $5.5 million on the Kansas Jayhawks to win the National Championship. Mack ended up cashing in on those wagers to win more than $10 million, but all that win did was soften the blow as he was running a promotion for customers that allowed them to win if Kansas won it all. </p><p> </p><p>Just chalk up another win for Mattress Mack, though, and he will continue making big wagers in the future, especially when it comes time for the NCAA Tournament. </p><p> </p><p> </p><p> </p><h2>8. 2022 Title Game Was Wild Ride</h2><p> </p><p>The 2022 National Championship Game not only had the attention of college basketball fans, but it also had the attention of sportsbooks. That was because North Carolina entered the NCAA Tournament with odds set at +2500 or higher when the tournament began, and several bettors got in on that action. </p><p> </p><p>One bettor had a $10,200 wager on the Tar Heels when the tournament started, and that could have cashed in at $255,000. Instead, it was a bettor that made a smart live bet that ended up cashing in. </p><p> </p><p>After the Jayhawks got down by 15 points at halftime, one bettor made a wager of more than $8,000 on the moneyline for a payout of more than $110,000. Sportsbooks were saved by the Kansas win, but some bettors were still able to cash in. </p><p> </p><figure class="image"><img src="https://imagedelivery.net/hoXdcCyL8VZtxGv-T1axXw/39de5625-57fe-4a4b-1f92-00587c28b900/public" alt="MM_BAYLOR"></figure><p> </p><h2>9. 2021 Tournament Hurts Bovada Sportsbook</h2><p> </p><p>The national championship for the Baylor Bears in 2021 was costly for Bovada Sportsbook, as they took a ton of futures wager on the team. Baylor had odds set at +425, and plenty of bettors loved those odds when the action began. </p><p> </p><p>One bettor decided to place a $8,705 wager on Baylor to cut down the nets, and it ended up paying out nearly $40,000. There were some tense moments during that run from Baylor, but one bettor was able to cash in. </p><h2>10. Wildcats Win Big For Bettor</h2><p> </p><p>The Villanova Wildcats were one of the favorites to win the NCAA Tournament at +450, and there were plenty of bets made on that team. Most bettors tend to go small when making a futures bet, as there is a ton of risk, but that wasn’t the case for everyone. </p><p> </p><p>One specific bettor fell in love with the Wildcats before the start of the 2018 NCAA Tournament and decided to place a bet of $5,000. While this win by Villanova didn’t necessarily cause a life-changing win, one bettor was still able to win over $22,000.</p><p> </p><figure class="table" ><table class="ck-table-resized"><colgroup><col ><col ><col ><col ></colgroup><tbody><tr><td ><p><strong>FanDuel</strong></p><p><a href="https://wlfanduel.adsrv.eacdn.com/C.ashx?btag=a_25884b_2436c_&affid=16446&siteid=25884&adid=2436&c="><img src="https://imagedelivery.net/hoXdcCyL8VZtxGv-T1axXw/f99a17cc-be99-4289-971b-8775de88fe00/public" alt="FanDuel-vertical-logo.png"></a></p></td><td ><p><strong>Bonus Offer</strong> </p><p><i><strong>No Sweat First Bet up to $1,000</strong></i><strong> </strong></p></td><td ><p><strong>Top Features</strong> </p><p>Huge Betting Menu </p><p>Quick Payouts </p><p>Reliable Mobile App </p></td><td ><a href="https://wlfanduel.adsrv.eacdn.com/C.ashx?btag=a_25884b_2436c_&affid=16446&siteid=25884&adid=2436&c="><strong>CLAIM OFFER</strong></a> </td></tr></tbody></table></figure><figure class="table" ><table class="ck-table-resized"><colgroup><col ><col ><col ><col ></colgroup><tbody><tr><td ><p><strong>DraftKings</strong> </p><p><a href="https://dksb.sng.link/As9kz/32n0?_dl=https%3A%2F%2Fsportsbook.draftkings.com%2Fgateway%3Fs%3D492657391%26wpcid%3D241916%26wpcn%3D1000DB%26wpsrc%3D8Count%2520Media%26wpcrid%3D%26wpscn%3D&pcid=241916"><img src="https://imagedelivery.net/hoXdcCyL8VZtxGv-T1axXw/5e9187a2-0da3-4c28-86c5-5aab37f0ec00/public" alt="draftkings-crown.jpg"></a></p></td><td ><p><strong>Bonus Offer</strong> </p><p><i><strong>$1,000 Deposit Bonus</strong></i><strong> </strong></p></td><td ><p><strong>Top Features</strong> </p><p>Great Live Betting Section </p><p>Same-Game Parlays </p><p>User-Friendly Interface </p></td><td ><a href="https://dksb.sng.link/As9kz/32n0?_dl=https%3A%2F%2Fsportsbook.draftkings.com%2Fgateway%3Fs%3D492657391%26wpcid%3D241916%26wpcn%3D1000DB%26wpsrc%3D8Count%2520Media%26wpcrid%3D%26wpscn%3D&pcid=241916"><strong>CLAIM OFFER</strong></a> </td></tr></tbody></table></figure><figure class="table" ><table class="ck-table-resized"><colgroup><col ><col ><col ><col ></colgroup><tbody><tr><td ><p><strong>Caesars</strong> </p><p><a href="https://wlwilliamhillus.adsrv.eacdn.com/C.ashx?btag=a_7111b_2486c_&affid=302&siteid=7111&adid=2486&c="><img src="https://imagedelivery.net/hoXdcCyL8VZtxGv-T1axXw/18c16f32-700f-4a97-3a40-ef9b1b8e8f00/public" alt="final_app_icon-circle.png"></a></p></td><td ><p><strong>Bonus Offer</strong> </p><p><i><strong>Get Up To $1,250 in Bet Credits</strong></i><strong> </strong></p></td><td ><p><strong>Top Features</strong> </p><p>A Wide Variety of Betting Options </p><p>Generous Welcome Bonus </p><p>Many Deposit Options </p></td><td ><a href="https://wlwilliamhillus.adsrv.eacdn.com/C.ashx?btag=a_7111b_2486c_&affid=302&siteid=7111&adid=2486&c="><strong>CLAIM OFFER</strong></a> </td></tr></tbody></table></figure><h2> </h2><h2>Biggest Bets in March Madness History FAQ</h2><h3>How much money is legally bet on March Madness?</h3><p>According to the American Gaming Association, Americans are expected to legally bet around $295 million during 2023 March Madness. However, there is still a large amount of money wagered at offshore books and with cash payments to local bookies.</p><p> </p><h3>Who is “Mattress Mack?”</h3><p>“Mattress Mack” is Jim McIngvale, a Texas business man who runs a furniture empire. He is also one of the most prominent sports bettors and is known for making massive wagers on sporting events. </p><p> </p><figure class="image"><img src="https://imagedelivery.net/hoXdcCyL8VZtxGv-T1axXw/42dbce25-c0ed-4b36-9e83-cc766de08c00/public" alt="Mattress Mack"></figure><p> </p><h3>Want To Learn More?</h3><p><a href="https://www.pickboss.com/march-madness-cinderella-teams/">Best March Madness Cinderella Teams in History</a><br><a href="https://www.pickboss.com/march-madness-mvp-odds">Who is The Favorite to Win March Madness MVP in 2023?</a><br><a href="https://www.pickboss.com/march-madness-parlay-betting/">March Madness Betting Parlays to Make in 2023</a><br><a href="https://www.pickboss.com/watch-march-madness-nyc/ ">Where to Watch NCAA Tournament in NYC</a><br><a href="https://www.pickboss.com/march-madness-betting-sites">March Madness Betting Sites: Where to Bet on NCAA Tournament 2023</a></p></div><div id="myModal" class="video-player"><div class="video-modal"></div></div></div><script>(STORAGE_KEY => { if (!window.history.state || !window.history.state.key) { let key = Math.random().toString(32).slice(2); window.history.replaceState({ key }, ""); } try { let positions = JSON.parse(sessionStorage.getItem(STORAGE_KEY) || "{}"); let storedY = positions[window.history.state.key]; if (typeof storedY === "number") { window.scrollTo(0, storedY); } } catch (error) { console.error(error); sessionStorage.removeItem(STORAGE_KEY); } })("positions")</script><link rel="modulepreload" href="/build/manifest-2F855925.js"/><link rel="modulepreload" href="/build/entry.client-K7BNY5Z5.js"/><link rel="modulepreload" href="/build/_shared/chunk-OVDSVEZR.js"/><link rel="modulepreload" href="/build/_shared/chunk-Q3IECNXJ.js"/><link rel="modulepreload" href="/build/_shared/chunk-I6VQKEYX.js"/><link rel="modulepreload" href="/build/_shared/chunk-IEIGYRW6.js"/><link rel="modulepreload" href="/build/root-SL4AUC7G.js"/><link rel="modulepreload" href="/build/_shared/chunk-HULVTPOF.js"/><link rel="modulepreload" href="/build/_shared/chunk-5GGGADPA.js"/><link rel="modulepreload" href="/build/_shared/chunk-UOJO4LFU.js"/><link rel="modulepreload" href="/build/_shared/chunk-75J5FNML.js"/><link rel="modulepreload" href="/build/_shared/chunk-F765U54Q.js"/><link rel="modulepreload" href="/build/routes/$articleSlug-GALBVPTI.js"/><script>window.__remixContext = {"appState":{"trackBoundaries":true,"trackCatchBoundaries":true,"catchBoundaryRouteId":null,"renderBoundaryRouteId":null,"loaderBoundaryRouteId":null},"matches":[{"params":{"articleSlug":"biggest-bets-march-madness-history"},"pathname":"/","route":{"id":"root","path":"","module":"/build/root-SL4AUC7G.js","imports":["/build/_shared/chunk-I6VQKEYX.js","/build/_shared/chunk-IEIGYRW6.js"],"hasAction":false,"hasLoader":true,"hasCatchBoundary":true,"hasErrorBoundary":false}},{"params":{"articleSlug":"biggest-bets-march-madness-history"},"pathname":"/biggest-bets-march-madness-history","route":{"id":"routes/$articleSlug","parentId":"root","path":":articleSlug","module":"/build/routes/$articleSlug-GALBVPTI.js","imports":["/build/_shared/chunk-HULVTPOF.js","/build/_shared/chunk-5GGGADPA.js","/build/_shared/chunk-UOJO4LFU.js","/build/_shared/chunk-75J5FNML.js","/build/_shared/chunk-F765U54Q.js"],"hasAction":false,"hasLoader":true,"hasCatchBoundary":false,"hasErrorBoundary":false}}],"routeData":{"root":{"navBarData":{"navBarItems":[{"label":"March Madness","order":0,"slug":"march-madness"},{"label":"NCAAB","order":1,"slug":"NCAAB"},{"label":"NFL","order":2,"slug":"nfl"},{"label":"NCAAF","order":3,"slug":"NCAAF"},{"label":"NBA","order":4,"slug":"nba"},{"label":"UFC","order":5,"slug":"ufc"}],"states":[{"fullName":"Arizona","shortCode":"AZ","isDefault":null},{"fullName":"Colorado","shortCode":"CO","isDefault":null},{"fullName":"Illinois","shortCode":"IL","isDefault":null},{"fullName":"Indiana","shortCode":"IN","isDefault":null},{"fullName":"Louisiana","shortCode":"LA","isDefault":null},{"fullName":"Michigan","shortCode":"MI","isDefault":null},{"fullName":"New York","shortCode":"NY","isDefault":null},{"fullName":"Tennessee","shortCode":"TN","isDefault":null},{"fullName":"Pennsylvania","shortCode":"PA","isDefault":null},{"fullName":"Iowa","shortCode":"IA","isDefault":null},{"fullName":"Ohio","shortCode":"OH","isDefault":true},{"fullName":"New Jersey","shortCode":"NJ","isDefault":false}]},"siteConfig":null,"clientEnv":{"REMIX_GA_TRACKING_ID":"G-9DDC6R4ZZZ","REMIX_GTM_ID":"GTM-WFD9CSL","REMIX_PUBLIC_8COUNT_EMBED_BASE_URL":"https://embed.8count.tv/embed"}},"routes/$articleSlug":{"articleData":{"id":1052,"attributes":{"content":"\u003cp\u003e\u0026nbsp;\u003c/p\u003e\u003cp\u003eThere are some great sporting events that take place each year, but few are more significant than the NCAA Tournament. March Madness has been popular for decades, but that popularity has only seemed to get bigger with the expansion of legal sports betting.\u0026nbsp;\u003c/p\u003e\u003cp\u003e\u0026nbsp;\u003c/p\u003e\u003cp\u003eWhile most bettors tend to make small bets during the NCAA Tournament, that is different from how some bettors go about it. There are some huge sports bettors out there, and they are looking to win big during March.\u0026nbsp;\u003c/p\u003e\u003cdiv class=\"raw-html-embed\"\u003e\u003ccenter\u003e\u003cdiv class=\"metabet-gametile metabet-size-728x90 metabet-query-534457\"\u003e\u003c/div\u003e\u003c/center\u003e\u003c/div\u003e\u003cdiv class=\"raw-html-embed\"\u003e\u003ccenter\u003e\u003cdiv class=\"metabet-gametile metabet-size-728x90 metabet-query-534464\"\u003e\u003c/div\u003e\u003c/center\u003e\u003c/div\u003e\u003cdiv class=\"raw-html-embed\"\u003e\u003ccenter\u003e\u003cdiv class=\"metabet-gametile metabet-size-728x90 metabet-query-534458\"\u003e\u003c/div\u003e\u003c/center\u003e\u003c/div\u003e\u003cdiv class=\"raw-html-embed\"\u003e\u003ccenter\u003e\u003cdiv class=\"metabet-gametile metabet-size-728x90 metabet-query-534474\"\u003e\u003c/div\u003e\u003c/center\u003e\u003c/div\u003e\u003ch2\u003e\u003cbr\u003eBiggest Bets in March Madness History\u003c/h2\u003e\u003cp\u003eMost of the biggest bets ever made on March Madness are going to be \u003ca href=\"https://www.pickboss.com/march-madness-parlay-betting\"\u003efutures betting\u003c/a\u003e, but there has been some big parlay hits as well. Here are 10 of the biggest bets and biggest wins during March Madness.\u0026nbsp;\u003c/p\u003e\u003cp\u003e{WIDGET}\u003c/p\u003e\u003ch2\u003e1. Florida -8 vs. Oral Roberts\u003c/h2\u003e\u003cp\u003e\u0026nbsp;\u003c/p\u003e\u003cp\u003eMost bettors tend to win big when betting on an underdog team, but that wasn’t the strategy used by one bettor a few years ago. After Oral Roberts pulled off a stunning upset over Ohio State as a 15-seed, one bettor decided to fade them in the next round.\u0026nbsp;\u003c/p\u003e\u003cp\u003e\u0026nbsp;\u003c/p\u003e\u003cp\u003eA bettor decided to make a $224,000 bet on the Gators to win and cover the eight-point spread. The reward would have been $204,000, and this bet was looking good in the first half, but things turned quickly.\u0026nbsp;\u003c/p\u003e\u003cp\u003e\u0026nbsp;\u003c/p\u003e\u003cp\u003eNot only did Florida end up failing to cover the spread, but Oral Roberts won the game and advanced all the way to the Sweet 16.\u0026nbsp;\u003c/p\u003e\u003cp\u003e\u0026nbsp;\u003c/p\u003e\u003ch2\u003e2. Tar Heels Come Up Short\u003c/h2\u003e\u003cp\u003e\u0026nbsp;\u003c/p\u003e\u003cp\u003eMaking a futures wager is a great way to win big, but you also take on a ton of risk. One bettor found out the hard way in 2019 as picking the favored North Carolina Tar Heels ended up being a significant loss of money.\u0026nbsp;\u003c/p\u003e\u003cp\u003e\u0026nbsp;\u003c/p\u003e\u003cp\u003eBefore the NCAA Tournament started in 2019, William Hill Sportsbook took on a $10,000 bet on the Tar Heels to cut down the nets. That would have paid out $80,000 and would have been a massive payday.\u0026nbsp;\u003c/p\u003e\u003cp\u003e\u0026nbsp;\u003c/p\u003e\u003cp\u003eThat bet ended early, though, as the Tar Heels failed even to reach the Final Four.\u0026nbsp;\u003c/p\u003e\u003cp\u003e\u0026nbsp;\u003c/p\u003e\u003ch2\u003e3. “Mattress Mack” in Action\u003c/h2\u003e\u003cp\u003e\u0026nbsp;\u003c/p\u003e\u003cp\u003eJim McIngvale is known as “Mattress Mack” due to his furniture store that he has in Texas, and he is also one of the biggest sports bettors in the country. Mattress Mack loves to make futures wagers, and you will struggle to find anyone that has the type of cash that he does.\u0026nbsp;\u003c/p\u003e\u003cp\u003e\u0026nbsp;\u003c/p\u003e\u003cp\u003eDuring the 2021 NCAA Tournament, Mattress Mack decided to place a $1 million wager on the Houston Cougars to win the title. That bet would have paid out $9 million, but ultimately the Cougars were defeated by the Baylor Bears in the Final Four.\u0026nbsp;\u003c/p\u003e\u003cp\u003e\u0026nbsp;\u003c/p\u003e\u003ch2\u003e4. Ohio State Ruins Big Bet\u003c/h2\u003e\u003cp\u003e\u0026nbsp;\u003c/p\u003e\u003cp\u003eAfter a runner-up finish in the 2021 Big Ten Tournament, the Ohio State Buckeyes were a trendy pick to make a deep run in the NCAA Tournament. They were getting so much attention that one bettor decided to wager $100,000 on them to win the National Championship.\u0026nbsp;\u003c/p\u003e\u003cp\u003e\u0026nbsp;\u003c/p\u003e\u003cp\u003eIf the Buckeyes were able to cut down the nets and win the title, it would have resulted in a multi-million dollar win for the bettor at William Hill Sportsbook. That bettor didn’t have to sweat out his bet long, though, as the Buckeyes lost in the first round, and William Hill was able to benefit from the poor bet.\u0026nbsp;\u003c/p\u003e\u003cp\u003e\u0026nbsp;\u003c/p\u003e\u003ch2\u003e5. Futures Parlay Goes to Waste\u003c/h2\u003e\u003cp\u003e\u0026nbsp;\u003c/p\u003e\u003cp\u003eFutures betting is usually a way to go if you want a big win, but coming to some future bets into a parlay can result in a massive payday. That was the strategy used by one bettor that looked to pick the eventual national champion.\u0026nbsp;\u003c/p\u003e\u003cp\u003e\u0026nbsp;\u003c/p\u003e\u003cp\u003eA bettor placed a combination future wager on four different college basketball programs, and just one of them had to win the national championship. This $100,000 bet included Duke, Gonzaga, Michigan, and Kansas, and all four teams were in the top-15 betting favorites.\u0026nbsp;\u003c/p\u003e\u003cp\u003e\u0026nbsp;\u003c/p\u003e\u003cp\u003eUnfortunately, none of those teams ended up even making the Final Four, and that bet was over before the final weekend. That was an interesting wager to make, but ultimately it resulted in a donation of $100,000.\u0026nbsp;\u003c/p\u003e\u003cp\u003e\u0026nbsp;\u003c/p\u003e\u003cp\u003e{VIDEO}\u003c/p\u003e\u003cp\u003e\u0026nbsp;\u003c/p\u003e\u003ch2\u003e6. A Chance at $47 Billion\u003c/h2\u003e\u003cp\u003e\u0026nbsp;\u003c/p\u003e\u003cp\u003eYou would think that in order to win $47 billion potentially, it would take a pretty massive wager. That wasn’t the case during the 2021 NCAA Tournament as one bettor had a chance to win that much money with a wager of just $0.10.\u0026nbsp;\u003c/p\u003e\u003cp\u003e\u0026nbsp;\u003c/p\u003e\u003cp\u003eThis was obviously a massive longshot bet, as the bettor included six huge underdogs in a six-leg moneyline parlay. There wasn’t a real threat of this bet ever hitting, but it was an impressive attempt at a chance to cash in with only six legs and a tiny stake.\u0026nbsp;\u003c/p\u003e\u003cp\u003e\u0026nbsp;\u003c/p\u003e\u003ch2\u003e7. Mattress Mack Cashes In\u003c/h2\u003e\u003cp\u003e\u0026nbsp;\u003c/p\u003e\u003cp\u003eMattress Mack is back on this list, but this time his bet wasn’t a futures bet at all. In fact, this bet was almost made out of desperation as Mattress Mack was potentially on the hook to lose millions at his furniture store in Texas.\u0026nbsp;\u003c/p\u003e\u003cp\u003e\u0026nbsp;\u003c/p\u003e\u003cp\u003eLast April, McIngvale had to take a helicopter ride to Louisiana in order to place two wagers worth up to $5.5 million on the Kansas Jayhawks to win the National Championship. Mack ended up cashing in on those wagers to win more than $10 million, but all that win did was soften the blow as he was running a promotion for customers that allowed them to win if Kansas won it all.\u0026nbsp;\u003c/p\u003e\u003cp\u003e\u0026nbsp;\u003c/p\u003e\u003cp\u003eJust chalk up another win for Mattress Mack, though, and he will continue making big wagers in the future, especially when it comes time for the NCAA Tournament.\u0026nbsp;\u003c/p\u003e\u003cp\u003e\u0026nbsp;\u003c/p\u003e\u003cp\u003e\u0026nbsp;\u003c/p\u003e\u003cp\u003e\u0026nbsp;\u003c/p\u003e\u003ch2\u003e8. 2022 Title Game Was Wild Ride\u003c/h2\u003e\u003cp\u003e\u0026nbsp;\u003c/p\u003e\u003cp\u003eThe 2022 National Championship Game not only had the attention of college basketball fans, but it also had the attention of sportsbooks. That was because North Carolina entered the NCAA Tournament with odds set at +2500 or higher when the tournament began, and several bettors got in on that action.\u0026nbsp;\u003c/p\u003e\u003cp\u003e\u0026nbsp;\u003c/p\u003e\u003cp\u003eOne bettor had a $10,200 wager on the Tar Heels when the tournament started, and that could have cashed in at $255,000. Instead, it was a bettor that made a smart live bet that ended up cashing in.\u0026nbsp;\u003c/p\u003e\u003cp\u003e\u0026nbsp;\u003c/p\u003e\u003cp\u003eAfter the Jayhawks got down by 15 points at halftime, one bettor made a wager of more than $8,000 on the moneyline for a payout of more than $110,000. Sportsbooks were saved by the Kansas win, but some bettors were still able to cash in.\u0026nbsp;\u003c/p\u003e\u003cp\u003e\u0026nbsp;\u003c/p\u003e\u003cfigure class=\"image\"\u003e\u003cimg src=\"https://imagedelivery.net/hoXdcCyL8VZtxGv-T1axXw/39de5625-57fe-4a4b-1f92-00587c28b900/public\" alt=\"MM_BAYLOR\"\u003e\u003c/figure\u003e\u003cp\u003e\u0026nbsp;\u003c/p\u003e\u003ch2\u003e9. 2021 Tournament Hurts Bovada Sportsbook\u003c/h2\u003e\u003cp\u003e\u0026nbsp;\u003c/p\u003e\u003cp\u003eThe national championship for the Baylor Bears in 2021 was costly for Bovada Sportsbook, as they took a ton of futures wager on the team. Baylor had odds set at +425, and plenty of bettors loved those odds when the action began.\u0026nbsp;\u003c/p\u003e\u003cp\u003e\u0026nbsp;\u003c/p\u003e\u003cp\u003eOne bettor decided to place a $8,705 wager on Baylor to cut down the nets, and it ended up paying out nearly $40,000. There were some tense moments during that run from Baylor, but one bettor was able to cash in.\u0026nbsp;\u003c/p\u003e\u003ch2\u003e10. Wildcats Win Big For Bettor\u003c/h2\u003e\u003cp\u003e\u0026nbsp;\u003c/p\u003e\u003cp\u003eThe Villanova Wildcats were one of the favorites to win the NCAA Tournament at +450, and there were plenty of bets made on that team. Most bettors tend to go small when making a futures bet, as there is a ton of risk, but that wasn’t the case for everyone.\u0026nbsp;\u003c/p\u003e\u003cp\u003e\u0026nbsp;\u003c/p\u003e\u003cp\u003eOne specific bettor fell in love with the Wildcats before the start of the 2018 NCAA Tournament and decided to place a bet of $5,000. While this win by Villanova didn’t necessarily cause a life-changing win, one bettor was still able to win over $22,000.\u003c/p\u003e\u003cp\u003e\u0026nbsp;\u003c/p\u003e\u003cfigure class=\"table\" style=\"width:48.73%;\"\u003e\u003ctable class=\"ck-table-resized\"\u003e\u003ccolgroup\u003e\u003ccol style=\"width:25.32%;\"\u003e\u003ccol style=\"width:24.92%;\"\u003e\u003ccol style=\"width:36.2%;\"\u003e\u003ccol style=\"width:13.56%;\"\u003e\u003c/colgroup\u003e\u003ctbody\u003e\u003ctr\u003e\u003ctd style=\"width:123px;\"\u003e\u003cp\u003e\u003cstrong\u003eFanDuel\u003c/strong\u003e\u003c/p\u003e\u003cp\u003e\u003ca href=\"https://wlfanduel.adsrv.eacdn.com/C.ashx?btag=a_25884b_2436c_\u0026amp;affid=16446\u0026amp;siteid=25884\u0026amp;adid=2436\u0026amp;c=\"\u003e\u003cimg src=\"https://imagedelivery.net/hoXdcCyL8VZtxGv-T1axXw/f99a17cc-be99-4289-971b-8775de88fe00/public\" alt=\"FanDuel-vertical-logo.png\"\u003e\u003c/a\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd style=\"width:123px;\"\u003e\u003cp\u003e\u003cstrong\u003eBonus Offer\u003c/strong\u003e\u0026nbsp;\u003c/p\u003e\u003cp\u003e\u003ci\u003e\u003cstrong\u003eNo Sweat First Bet up to $1,000\u003c/strong\u003e\u003c/i\u003e\u003cstrong\u003e\u0026nbsp;\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd style=\"width:123px;\"\u003e\u003cp\u003e\u003cstrong\u003eTop Features\u003c/strong\u003e\u0026nbsp;\u003c/p\u003e\u003cp\u003eHuge Betting Menu\u0026nbsp;\u003c/p\u003e\u003cp\u003eQuick Payouts\u0026nbsp;\u003c/p\u003e\u003cp\u003eReliable Mobile App\u0026nbsp;\u003c/p\u003e\u003c/td\u003e\u003ctd style=\"width:123px;\"\u003e\u003ca href=\"https://wlfanduel.adsrv.eacdn.com/C.ashx?btag=a_25884b_2436c_\u0026amp;affid=16446\u0026amp;siteid=25884\u0026amp;adid=2436\u0026amp;c=\"\u003e\u003cstrong\u003eCLAIM OFFER\u003c/strong\u003e\u003c/a\u003e\u0026nbsp;\u003c/td\u003e\u003c/tr\u003e\u003c/tbody\u003e\u003c/table\u003e\u003c/figure\u003e\u003cfigure class=\"table\" style=\"width:48.45%;\"\u003e\u003ctable class=\"ck-table-resized\"\u003e\u003ccolgroup\u003e\u003ccol style=\"width:25%;\"\u003e\u003ccol style=\"width:25.2%;\"\u003e\u003ccol style=\"width:36.58%;\"\u003e\u003ccol style=\"width:13.22%;\"\u003e\u003c/colgroup\u003e\u003ctbody\u003e\u003ctr\u003e\u003ctd style=\"width:123px;\"\u003e\u003cp\u003e\u003cstrong\u003eDraftKings\u003c/strong\u003e\u0026nbsp;\u003c/p\u003e\u003cp\u003e\u003ca href=\"https://dksb.sng.link/As9kz/32n0?_dl=https%3A%2F%2Fsportsbook.draftkings.com%2Fgateway%3Fs%3D492657391%26wpcid%3D241916%26wpcn%3D1000DB%26wpsrc%3D8Count%2520Media%26wpcrid%3D%26wpscn%3D\u0026amp;pcid=241916\"\u003e\u003cimg src=\"https://imagedelivery.net/hoXdcCyL8VZtxGv-T1axXw/5e9187a2-0da3-4c28-86c5-5aab37f0ec00/public\" alt=\"draftkings-crown.jpg\"\u003e\u003c/a\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd style=\"width:123px;\"\u003e\u003cp\u003e\u003cstrong\u003eBonus Offer\u003c/strong\u003e\u0026nbsp;\u003c/p\u003e\u003cp\u003e\u003ci\u003e\u003cstrong\u003e$1,000 Deposit Bonus\u003c/strong\u003e\u003c/i\u003e\u003cstrong\u003e\u0026nbsp;\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd style=\"width:123px;\"\u003e\u003cp\u003e\u003cstrong\u003eTop Features\u003c/strong\u003e\u0026nbsp;\u003c/p\u003e\u003cp\u003eGreat Live Betting Section\u0026nbsp;\u003c/p\u003e\u003cp\u003eSame-Game Parlays\u0026nbsp;\u003c/p\u003e\u003cp\u003eUser-Friendly Interface\u0026nbsp;\u003c/p\u003e\u003c/td\u003e\u003ctd style=\"width:123px;\"\u003e\u003ca href=\"https://dksb.sng.link/As9kz/32n0?_dl=https%3A%2F%2Fsportsbook.draftkings.com%2Fgateway%3Fs%3D492657391%26wpcid%3D241916%26wpcn%3D1000DB%26wpsrc%3D8Count%2520Media%26wpcrid%3D%26wpscn%3D\u0026amp;pcid=241916\"\u003e\u003cstrong\u003eCLAIM OFFER\u003c/strong\u003e\u003c/a\u003e\u0026nbsp;\u003c/td\u003e\u003c/tr\u003e\u003c/tbody\u003e\u003c/table\u003e\u003c/figure\u003e\u003cfigure class=\"table\" style=\"width:48.45%;\"\u003e\u003ctable class=\"ck-table-resized\"\u003e\u003ccolgroup\u003e\u003ccol style=\"width:25%;\"\u003e\u003ccol style=\"width:25%;\"\u003e\u003ccol style=\"width:36.59%;\"\u003e\u003ccol style=\"width:13.41%;\"\u003e\u003c/colgroup\u003e\u003ctbody\u003e\u003ctr\u003e\u003ctd style=\"width:123px;\"\u003e\u003cp\u003e\u003cstrong\u003eCaesars\u003c/strong\u003e \u0026nbsp;\u003c/p\u003e\u003cp\u003e\u003ca href=\"https://wlwilliamhillus.adsrv.eacdn.com/C.ashx?btag=a_7111b_2486c_\u0026amp;affid=302\u0026amp;siteid=7111\u0026amp;adid=2486\u0026amp;c=\"\u003e\u003cimg src=\"https://imagedelivery.net/hoXdcCyL8VZtxGv-T1axXw/18c16f32-700f-4a97-3a40-ef9b1b8e8f00/public\" alt=\"final_app_icon-circle.png\"\u003e\u003c/a\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd style=\"width:123px;\"\u003e\u003cp\u003e\u003cstrong\u003eBonus Offer\u003c/strong\u003e\u0026nbsp;\u003c/p\u003e\u003cp\u003e\u003ci\u003e\u003cstrong\u003eGet Up To $1,250 in Bet Credits\u003c/strong\u003e\u003c/i\u003e\u003cstrong\u003e\u0026nbsp;\u003c/strong\u003e\u003c/p\u003e\u003c/td\u003e\u003ctd style=\"width:123px;\"\u003e\u003cp\u003e\u003cstrong\u003eTop Features\u003c/strong\u003e\u0026nbsp;\u003c/p\u003e\u003cp\u003eA Wide Variety of Betting Options\u0026nbsp;\u003c/p\u003e\u003cp\u003eGenerous Welcome Bonus\u0026nbsp;\u003c/p\u003e\u003cp\u003eMany Deposit Options\u0026nbsp;\u003c/p\u003e\u003c/td\u003e\u003ctd style=\"width:123px;\"\u003e\u003ca href=\"https://wlwilliamhillus.adsrv.eacdn.com/C.ashx?btag=a_7111b_2486c_\u0026amp;affid=302\u0026amp;siteid=7111\u0026amp;adid=2486\u0026amp;c=\"\u003e\u003cstrong\u003eCLAIM OFFER\u003c/strong\u003e\u003c/a\u003e\u0026nbsp;\u003c/td\u003e\u003c/tr\u003e\u003c/tbody\u003e\u003c/table\u003e\u003c/figure\u003e\u003ch2\u003e\u0026nbsp;\u003c/h2\u003e\u003ch2\u003eBiggest Bets in March Madness History FAQ\u003c/h2\u003e\u003ch3\u003eHow much money is legally bet on March Madness?\u003c/h3\u003e\u003cp\u003eAccording to the American Gaming Association, Americans are expected to legally bet around $295 million during 2023 March Madness. However, there is still a large amount of money wagered at offshore books and with cash payments to local bookies.\u003c/p\u003e\u003cp\u003e\u0026nbsp;\u003c/p\u003e\u003ch3\u003eWho is “Mattress Mack?”\u003c/h3\u003e\u003cp\u003e“Mattress Mack” is Jim McIngvale, a Texas business man who runs a furniture empire. He is also one of the most prominent sports bettors and is known for making massive wagers on sporting events.\u0026nbsp;\u003c/p\u003e\u003cp\u003e\u0026nbsp;\u003c/p\u003e\u003cfigure class=\"image\"\u003e\u003cimg src=\"https://imagedelivery.net/hoXdcCyL8VZtxGv-T1axXw/42dbce25-c0ed-4b36-9e83-cc766de08c00/public\" alt=\"Mattress Mack\"\u003e\u003c/figure\u003e\u003cp\u003e\u0026nbsp;\u003c/p\u003e\u003ch3\u003eWant To Learn More?\u003c/h3\u003e\u003cp\u003e\u003ca href=\"https://www.pickboss.com/march-madness-cinderella-teams/\"\u003eBest March Madness Cinderella Teams in History\u003c/a\u003e\u003cbr\u003e\u003ca href=\"https://www.pickboss.com/march-madness-mvp-odds\"\u003eWho is The Favorite to Win March Madness MVP in 2023?\u003c/a\u003e\u003cbr\u003e\u003ca href=\"https://www.pickboss.com/march-madness-parlay-betting/\"\u003eMarch Madness Betting Parlays to Make in 2023\u003c/a\u003e\u003cbr\u003e\u003ca href=\"https://www.pickboss.com/watch-march-madness-nyc/\u0026nbsp;\"\u003eWhere to Watch NCAA Tournament in NYC\u003c/a\u003e\u003cbr\u003e\u003ca href=\"https://www.pickboss.com/march-madness-betting-sites\"\u003eMarch Madness Betting Sites: Where to Bet on NCAA Tournament 2023\u003c/a\u003e\u003c/p\u003e","title":"The 10 Biggest Bets In March Madness History","createdAt":"2023-02-23T13:40:57.556Z","updatedAt":"2023-03-24T09:05:39.149Z","publishedAt":"2023-03-24T09:05:39.143Z","slug":"biggest-bets-march-madness-history","author":{"data":{"id":1,"attributes":{"name":"PickBoss","description":null,"createdAt":"2022-11-14T13:25:52.130Z","updatedAt":"2022-11-14T13:25:54.389Z","publishedAt":"2022-11-14T13:25:54.386Z","image":{"data":null}}}},"tags":{"data":[{"id":3,"attributes":{"name":"Betting Guides","type":"other","createdAt":"2022-11-19T15:14:51.759Z","updatedAt":"2022-11-23T15:39:44.380Z","publishedAt":"2022-11-19T15:14:53.001Z","order":3,"isNavBarItem":false,"slug":"betting-guides","parent":{"data":null},"tags":{"data":[]}}},{"id":7,"attributes":{"name":"Basketball","type":"sport","createdAt":"2023-01-19T18:11:21.491Z","updatedAt":"2023-01-19T18:11:22.793Z","publishedAt":"2023-01-19T18:11:22.788Z","order":0,"isNavBarItem":false,"slug":"basketball","parent":{"data":null},"tags":{"data":[{"id":10,"attributes":{"name":"March Madness","type":"league","createdAt":"2023-02-14T10:46:45.722Z","updatedAt":"2023-02-21T08:43:12.413Z","publishedAt":"2023-02-14T10:47:01.275Z","order":0,"isNavBarItem":true,"slug":"march-madness"}},{"id":11,"attributes":{"name":"NCAAB","type":"league","createdAt":"2023-02-21T08:41:53.446Z","updatedAt":"2023-02-21T08:43:12.431Z","publishedAt":"2023-02-21T08:42:49.407Z","order":1,"isNavBarItem":true,"slug":"NCAAB"}},{"id":8,"attributes":{"name":"NBA","type":"league","createdAt":"2023-01-19T18:11:40.697Z","updatedAt":"2023-02-21T08:43:12.481Z","publishedAt":"2023-01-19T18:11:42.212Z","order":4,"isNavBarItem":true,"slug":"nba"}}]}}},{"id":10,"attributes":{"name":"March Madness","type":"league","createdAt":"2023-02-14T10:46:45.722Z","updatedAt":"2023-02-21T08:43:12.413Z","publishedAt":"2023-02-14T10:47:01.275Z","order":0,"isNavBarItem":true,"slug":"march-madness","parent":{"data":{"id":7,"attributes":{"name":"Basketball","type":"sport","createdAt":"2023-01-19T18:11:21.491Z","updatedAt":"2023-01-19T18:11:22.793Z","publishedAt":"2023-01-19T18:11:22.788Z","order":0,"isNavBarItem":false,"slug":"basketball"}}},"tags":{"data":[]}}},{"id":11,"attributes":{"name":"NCAAB","type":"league","createdAt":"2023-02-21T08:41:53.446Z","updatedAt":"2023-02-21T08:43:12.431Z","publishedAt":"2023-02-21T08:42:49.407Z","order":1,"isNavBarItem":true,"slug":"NCAAB","parent":{"data":{"id":7,"attributes":{"name":"Basketball","type":"sport","createdAt":"2023-01-19T18:11:21.491Z","updatedAt":"2023-01-19T18:11:22.793Z","publishedAt":"2023-01-19T18:11:22.788Z","order":0,"isNavBarItem":false,"slug":"basketball"}}},"tags":{"data":[]}}}]},"widget_offer":{"data":{"id":8,"attributes":{"header":"DraftKings","ctaLabel":"CLAIM NOW","termsAndConditions":"Physically present in AZ/CO/IL/IN/IA/LA(select parishes)/MI/NJ/NY/PA/TN/OH. 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