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4 Biggest Baseball Sports Betting Wins


Baseball is often called America’s pastime. But the popularity of Major League Baseball has dipped over the last two decades. It’s falling behind the NBA and the NFL that rules the roost in sheer revenue.

But baseball has as rich of a history as gambling itself.

Let’s take a look at the biggest baseball sports betting wins of all time.

1 – St. Louis Cardinals Win Big for Anonymous Gambler

The 2011 St. Louis Cardinals broke the hearts of the Texas Rangers and their legion of fans. The team was one strike away from defeat when they miraculously came back to win Game 6.

That Game 6 win tied the series at 3-3. However, it did more than net the W. The shocking comeback set the stage for a Game 7 that had the Cardinals riding the highest of highs and the Rangers reeling.

MLB staff had already taken the players’ families and press to the Rangers locker room to enjoy the celebration when fortunes shifted. Dallas media had gone so far as to announce a Rangers World Series title.

The Cardinals went on to win Game 7 and the World Series, making their dream of becoming World Champions come true.

They also made dreams come true for an anonymous bettor. The anonymous gambler strolled casually into the sportsbook at the MGM in Vegas and placed two very profitable bets.

The savvy man or woman put a simple $250 bet on the team to win the National League pennant. They then placed a second even more lucrative bet that St. Louis would become the World Series champions.

The secretive bettor that placed the two bets totaling $500 could cash out those tickets for a whopping $375,000.

That’s an insane return on investment and one phenomenal pick. I hope they are enjoying their handsome earnings.

2 – Kansas City Crushes It for “Vegas Dave”

Dave Oancea has become somewhat of a celebrity among sports bettors and Las Vegas casino gamblers. Before “Vegas Dave” was selling baseball cards for a record-breaking $4 million, he placed big-time bets on baseball.

After only one week of MLB action in the 2015 season, Vegas Dave had seen all he needed to place a massive bet on the World Series.

The Kansas City Royals came out of the gate red hot. They made it through their first seven games undefeated. Jumping out at 7-0 is impressive, but certainly not unheard of in the MLB.

That’s why many people quietly snickered at Oancea when he placed his bet on the Royals to win it all. Dave knew exactly what he was doing, and he trusted his knowledge enough to recognize the massive value.

Vegas Dave got 30/1 odds on the significant risk. Those 30/1 odds would bay at a pretty solid return on even a modest wager.

Dave didn’t place a small bet at all. Many sharp sports bettors may have opted for a $10,000 bet. Indeed, that’s a large bet and a potential payday of $300k. That’s several good years for many professional sports bettors.

Instead, Oancea decided to spread $140,000 over a dozen Vegas sportsbooks.

Kansas City made it through the regular season and playoffs to face the New York Mets in the World Series. The Royals never let it get interesting, dispatching the Mets in five games.

Vegas Dave hit a grand slam with this best and cashed his winning tickets in for a smooth $2.5 million.

3 – Let It Ride

During the 2017 World Series, the Houston Astros faced off against the Los Angeles Dodgers. Another anonymous gambler placed a significant wager on Game 1 and won.

They then pushed all-in on Game 2 and again won the bet. The stealthy punter didn’t stop there, though. They made winning bets on five straight games in the series, winning all five and letting it ride on the next game.

By Game 6, the anonymous sports bettor placed a jaw-dropping $8 million on the Dodgers to win it and force a Game 7.

I don’t know how much money you need to have to risk $8 million on a baseball game. I’m guessing $8,000,001, but realistically, it must be in the billions.

LA took care of their end and snatched a 3-1 victory from Houston. This win netted our incognito friend $14 million.

That number makes this win not only the biggest baseball sports bet win of all time, but the biggest win in the history of sports betting.

The 2017 World Series would later become part of one of the biggest scandals in the game’s history.

Allegations of the Houston Astros using technology to cheat during the season, including the World Series, was confirmed by a former player.

The cheating scandal rocked the baseball world, and several managers and executives lost their jobs as part of the fallout.

The MLB levied severe penalties against Houston but stopped short of stripping the team of their title. However, they did lose valuable draft picks and paid a substantial fine.

Not one of the vilified Houston players received any suspensions from the league. However, they had better be quick on their feet standing in the batter’s box this season.

We still don’t know who the mystery millionaire or perhaps billionaire is. Still, he’s rumored to reside somewhere in Eastern Europe.

Whoever the “Let It Ride” gambler is, he certainly has nerves of steel. Laying a wager of that gigantic proportion is not for the weak of heart.

4 – Mattress Mack

It would be a disservice to all of the biggest baseball sports betting wins if we didn’t take a look at one of the biggest baseball sports betting fails.

That dubious honor belongs to Jim McIngvale, the eccentric owner of Gallery Furniture in Houston, TX. You may not recognize the name, but you’ve probably heard of him as the infamous “Mattress Mack.”

In 2017, Mattress Mack ran a promotion that if the Houston Astros won the World Series, he would refund all mattress purchases over $3,000. Unfortunately for Mack, the Astros surprised many in the sports world.

The team won the World Series in seven games against the Dodgers, and as I mentioned above, the scandal that would follow put a terrible stain on the franchise.

Nevertheless, the promotion cost Mattress Mack over $10,000,000. But Mack is a betting man, and that year, he traveled to Las Vegas to bet on his favorite team to win the world series. The bet was over $1 million, to help absorb some of the eight-figure sting.

The 2019 MLB season saw the Houston Astros returning to the World Series. Mattress Mack was again looking to mitigate the potential losses from his popular promotion.

McIngvale traveled to nearby Biloxi, MS, to place a $3.5 million bet on his beloved Astros at the Scarlet Pearl. That is a massive wager and believed to be the biggest sports bet in Mississippi gaming history.

Mattress Mack didn’t stop there. He also placed a $1.5 million bet with the DraftKings sportsbook at the Meadowlands in New Jersey.

That wager is believed to be the most massive online bet in the state’s brief history of legal sports betting. It also brought Mattress Mack’s total investment on the series to over $5 million. The furniture business must be doing great.

With more money riding on the line than anyone in baseball sports betting history, Mack waited in eager anticipation.

Houston lost the first two games of the series and fell behind 0-2. Then, they roared back to life, winning three consecutive games and taking a series lead of 3-2.

Houston fans must’ve thought they had the World Series cinched up being just one win away from victory. However, it was not to be. The Nationals won the next two games and the World Series.

Mattress Mack lost over $5 million that season. Although, it’s unclear whether or not he was broken up over the loss. Based on the 2017 results, the loss may have saved him at least $5,000,000.

My dad lost $500 on the Dallas Cowboys when Dwight Clark made “The Catch,” and he has hated the Dallas Cowboys since that day. I wonder if Mattress Mack has left the dark side and become a Rangers fan?


As you can see, baseball has had some incredibly lucrative sports betting wins. It’s also not immune to kicking some bettors straight to the gut, as is the beast’s nature.

Whether you are a whale, like our mystery man in Eastern Europe laying $8 million on a single game or betting $20 on the series, sports betting on baseball can jump the excitement to an 11.

What’s your biggest baseball sports betting win?

Michael Stevens

Michael Stevens has been researching and writing topics involving the gambling industry for well over a decade now and is considered an expert on all things casino and sports betting. Michael has been writing for since early 2016. …

View all posts by Michael Stevens

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