The Largest Sports Betting Wins In History

Today's email breaks down the overall size of the sports betting market and details some of the biggest winners in history.


In the effort of keeping things fresh and showcasing additional content, context, and perspective, I try to publish a guest post on a relevant topic at least once every one to two months.

Today, you’re in luck.

Michael Sutyak, who runs a popular sports betting newsletter called Bettor Secrets (think Morning Brew for Sports Betting), has written up a detailed analysis on the overall size of the sports betting market and a few of his favorite bets in history.


The Quick Action: Market Size & The Biggest Sports Betting Wins

The size of the “illegal” sports betting market

It is tough to overstate the world’s appetite for gambling.  Lottos, casinos, sports betting. You name the event or activity and you can probably bet on it somewhere.  And even if you can’t bet on something currently, you can likely pull a bookie aside and have him generate a bet for you. 

In the US, even some of our most hallowed institutions participate in and facilitate betting. Investment banks are the biggest bookies of all (“The Big Short” anyone?).

But, few things captivate the human imagination and fire as much as sporting events when it comes to throwing down bets.    

The global sports betting industry reached a market size of $203 billion in 2020.  Within this industry, there were approximately 197 thousand employees in a total of almost 31 thousand businesses.

And this is just for legal, on-the-books sports betting.   

According to estimates from the American Gaming Association, Americans alone gamble more than $150 billion illegally on sports in a year. Because I saw this questioned (and hey, I get it - the American Gaming Association has a vested interest in this becoming legalized anyway you slice it), I saw another calculation.  

If people in the U.S. are allowed to make bets at the same rate as in the U.K. (where sports betting is legal), the industry's size would be about $67 billion a year. Even with that low ball figure, that’s an enormous industry.

Compare that to the $11.3 billion a year that Americans spend on tickets to movies (from 2019 because 2020 doesn’t count).

Or the ~ $10B a year Americans spend on the sporting event tickets themselves.

This is to say nothing of the folks that would place wagers if there were legal channels for them to use and open advertising across channels like Google Adwords (they’re slowly easing restrictions).

It should be a secret to no one that full legalization of sports betting is imminent in the US. Over 25 states have already passed legislation allowing at least some form of sports betting (online or at in-person sportsbooks), and more states will legalize sports gambling in the aftermath of the Supreme Court’s 2018 decision to strike down a 1992 federal law banning betting in most states.

And honestly, given the events of the past couple of months, I believe this sums it up best:

The Super Bowl has come and gone (a regular jubilee of sports gambling excess).  Roughly 100 million people watched the Kansas City Chiefs take on the Tampa Bay Buccaneers in Super Bowl 55.

So, while America nurses its betting hangover for a couple of days, I thought it would be interesting to dig into some of the more unique and most significant paying sports bets ever.  

Here are 5 of my favorites.

Largest Sports Betting Wins In History

1. Tiger Woods Masters Bet

  • Invested: $85K

  • Paid Out: $1.2M

  • Return: 1,312%

Tiger has had his struggles recently, and what used to be a relatively sure bet has become less so. But there are some stone-cold bettors out there, and we tip our cap to James Adducci.

He put down an $85,000 wager on Woods to win the 2019 Masters at the William Hill sportsbook with 14/1 odds. Adducci was paid out $1.2 million for his troubles.

The kicker? 

It was his first-ever sports bet. 

2. Kansas City Royals Future

  • Invested: $100K

  • Paid Out: $2.5M

  • Return: 2,400%

He may be obnoxious, his takes may be spicy, but love him or hate him, “Vegas Dave” Oancea has brought home some major winners.

In 2015, he bet $100K at 30/1 for the Kansas City Royals to win the World Series and even had to spread it across 15 different casinos because none would take such an enormous liability.

The Royals won the 2015 World Series - and Vegas Dave scooped $2.5M.

3. 15-Leg NFL Parlay

  • Invested: $5

  • Paid Out: $105K

  • Return: 2,099,900%

Yea, that’s not a typo. That’s not $5K; that’s $5. A Lincoln.

For those not familiar, a parlay is a series of bets that you need to win in order to pay out. It’s tough to win 3 or even 2 leg parlays. But Tayla Polia took a flyer on a 15-leg parlay at 20,000/1.

Even more amazing?

Her parlay included 5 underdogs on the moneyline (and 9 favorites). When it hit, Polia took home $105K. Easy game.

It was her second-ever bet. I guess there is such a thing as beginner’s luck.           

4. Leicester City Premier League Future

  • Invested: £100

  • Paid Out: £200,000

  • Return: 199,900%

The English Premier League is one of those leagues where the cream tends to rise to the top. 

Since 2010, only 5 teams have won the league: Manchester United, Manchester City, Chelsea, and Liverpool — and in 2015, Leicester City. 

Starting that season, Leicester was a 5000/1 dog. But someone was able to turn £100 into £200,000 by laying on them to win. It’s hard to overstate this level of upset (soccer fanatics will tell you). 

5. Phil Mickelson Baltimore Ravens Future

  • Invested: $20K

  • Paid Out: $560K

  • Return: 2,700%

It’s somewhat odd to hear that the athletes themselves put down sports betting wagers — but they can, and they do.

Phil Mickelson, Lefty himself, put $20K down on the Baltimore Ravens in the ‘00/’01 season at 22/1 odds before the season beginning.

Once the Ravens won the Super Bowl, Phil took home $560K.

The real question?

How much he has gambled with guys like Michael Jordan and Tiger Woods out on the links.

If you enjoyed this email, make sure to check out Michael Sutyak’s newsletter Bettor Secrets, which focuses on '“sports betting news, tips, and tricks from sharps you can’t get anywhere else.”

Sign Up Here!

Have a great day, and we’ll talk tomorrow.

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